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Sideways (2004)
Comedy, Drama, Romance

Sideways (2004)

A week before his friend Jack is to be married, best man Miles and the prospective groom head off to wine country for a week of fun, relaxation and - of course - wine drinking. Miles is the oenophile and does his best to teach Jack a bit about the art of appreciating great wine. All Jack cares about is drinking and carousing, something he accomplishes when he meets the attractive Stephanie at one of the vineyards. Miles is something of a sad sack, a high school English teacher who is a failed writer at heart. He has yet to get over the fact that his wife has divorced him and that she has remarried and he now faces that nerve racking wait for word from a prospective publisher. Miles has an opportunity to start anew when he meets Stephanie's friend Maya but when he let's slip that Jack is about to be married any hope of a relationship seems to be lost. (Read More)

Themes:writing, unfaithfulness, depression, theft, divorce, wedding, drunkenness, infidelity, marriage, friendship
Mood:satire
Locations:motel, restaurant, beach, hospital
Characters:writer, actor, waitress, teacher, lust
Story:wine, golf course, wine tasting, san diego california, road trip, wedding ceremony, los angeles california, fast food restaurant, academic masters degree, talking dirty during sex, failed artist, car crashing into a tree, money roll, knocking on door, makeup sex, sex with fat woman, tanker truck, middle age romance, fling, jazz score

About Schmidt (2002)
Comedy, Drama

About Schmidt (2002)

Warren Schmidt has led a safe, predictable life working in the insurance industry in Omaha, Nebr. for many years, yet now faces retirement. At the same time he is forced to take a hard look at his wife, his life and his relationship with his estranged daughter. An often hilarious series of events follow as Schmidt embarks on an unpredictable RV journey to attend his daughter's wedding in Denver. (Read More)

Themes:depression, wedding, infidelity, marriage
Mood:satire
Locations:restaurant
Story:highway travel, based on novel, midlife crisis, divorcee, medication, answering machine, on the road, road movie, road trip

Almost Famous (2000)
Adventure, Comedy, Drama, Music

Almost Famous (2000)

William Miller is a 15-year-old kid hired by Rolling Stone magazine to tour with and write about Stillwater, an up and coming rock band. This wonderfully witty coming-of-age film follows William as he falls face first to confront life, love, and lingo.

Themes:unfaithfulness, drunkenness, infidelity, friendship
Characters:teacher
Story:san diego california, los angeles california, sexual attraction, premarital sex, on the road, scantily clad female, california, road trip, cleavage, guitar, marijuana, birthday, telephone call, mother son relationship

American Wedding (2003)
Comedy, Romance

American Wedding (2003)

Jim Levenstein has finally found the courage to ask his girlfriend, Michelle Flaherty to marry him. She agrees to get married, but the problems don't stop there for Jim. Now along with Paul Finch and Kevin Myers, Jim must plan the wedding. Unfortunately Steve Stifler is in town and won't let the wedding go past without having some fun himself, which includes setting up a secret bachelor party. (Read More)

Themes:wedding, marriage, friendship
Locations:restaurant, beach
Characters:lust
Story:bachelor, highway travel, deceit, sexual attraction, premarital sex, on the road, scantily clad female, gay slur, cleavage, small town, telephone call, leg spreading, mother son relationship

American Beauty (1999) is one of the best movies like Sideways (2004)
Drama, Romance

American Beauty (1999)

After his death sometime in his forty-third year, suburbanite Lester Burnham tells of the last few weeks of his life, during which he had no idea of his imminent passing. He is a husband to real estate agent Carolyn Burnham and father to high school student Janie Burnham. Although Lester and Carolyn once loved each other, they now merely tolerate each other. Typical wallflower Janie too hates both her parents, the three who suffer individually in silence in their home life. Janie tries to steer clear of both her parents. Carolyn, relatively new to the real estate business, wants to create the persona of success to further her career, she aspiring to the professional life of Buddy Kane, the king of the real estate business in their neighborhood. Lester merely walks mindlessly through life, including at his job in advertising. His company is downsizing, and he, like all the other employees, has to justify his position to the newly hired efficiency expert to keep his job. Things change for Lester when he falls in love at first sight with Janie's more experienced classmate, Angela Hays. Both Janie and Angela can see Lester's sexual infatuation with Angela, who courts such attention from any man as a sign that she is model material, she having once appeared in Seventeen and it a career to which she aspires. Lester's infatuation with Angela gives him a reenergized view on life, where he openly doesn't care anymore what anyone thinks about what he does, anyone except Angela. This infatuation coincides with the Fittses moving in next door: homophobic disciplinarian US Marine Colonel Frank Fitts who rules the house with a military fist (that fist being both figurative and literal), his semi-comatose wife Barbara Fitts, and their bright and quietly subversive eighteen year old son Ricky Fitts, who openly abides by his father's rules while behind the scenes lives by his own quite different perspective. Much like Lester's infatuation, Ricky immediately becomes infatuated with Janie, he who considers girls like Angela as ordinary. The entry of Angela and the Fittses into the Burnhams' lives ultimately leads to each of the players confronting what is truly in his or her heart. (Read More)

Themes:unfaithfulness, depression, infidelity, friendship
Mood:satire
Locations:motel, restaurant
Characters:lust, writer
Story:fast food restaurant, fast food, buddy, talking dirty during sex, middle age, midlife crisis, deceit, unfaithful wife, premarital sex, scantily clad female, gay slur, cleavage, marijuana, extramarital affair, bare butt, sex in bed, small town, mother son relationship, sex scene

Along Came Polly (2004)
Comedy, Romance

Along Came Polly (2004)

Reuben Feffer thinks he's found the love of his life but on his honeymoon he discovers her cheating on him with a scuba instructor. Reuben travels back home to get his life on track. On a night out with best pal, Sandy Lyle, Reuben discovers an old school friend, Polly Prince. Reuben feels a connection straight away, and tries constantly to get her to like him. But it's not going to be easy for Reuben, especially when he spends his days calculating risks, and when someone unexpected turns up. This is why Along Came Polly (2004) is one of the best movies like Sideways (2004). (Read More)

Themes:unfaithfulness, wedding, infidelity, marriage, friendship
Locations:restaurant, beach
Characters:waitress, writer, actor
Story:los angeles california, fling, crawling, unfaithful wife, womanizer, answering machine, golf, wine, marijuana, extramarital affair, sex in bed, telephone call, mother son relationship, sex scene

Nocturnal Animals (2016)
Crime, Drama, Romance, Thriller

Nocturnal Animals (2016)

A "story inside a story," in which the first part follows a woman named Susan who receives a book manuscript from her ex-husband, a man whom she left 20 years earlier, asking for her opinion. The second element follows the actual manuscript, called "Nocturnal Animals," which revolves around a man whose family vacation turns violent and deadly. It also continues to follow the story of Susan, who finds herself recalling her first marriage and confronting some dark truths about herself. (Read More)

Themes:divorce, drunkenness, infidelity, marriage
Locations:motel, restaurant
Characters:writer
Story:los angeles california, based on novel, novel, man crying, unfaithful wife, crying man, author, diner, road trip, gay slur, extramarital affair, car accident, independent film

Closer (2004)
Drama, Romance

Closer (2004)

Smart-but-ineffectual journalist Dan "We use euphemisms!" cannot decide between his girlfriend, loving-but-clingy waitress Alice, or his lover cold-but-intellectual photographer Anna; herself indecisive between Dan and honest-but-thuggish "You're bloody gorgeous!" doctor Larry. The film puts the four leading characters in a box and strips them apart. (Read More)

Themes:unfaithfulness, depression, divorce, infidelity, marriage
Locations:restaurant, hospital
Characters:lust, waitress, writer
Story:cheating on girlfriend, divorcee, unfaithful wife, sexual attraction, scantily clad female, cleavage, birthday, extramarital affair, car accident, independent film, one word title, sex scene

As Good As It Gets (1997) is one of the best movies like Sideways (2004)
Comedy, Drama, Romance

As Good As It Gets (1997)

New York City. Melvin Udall, a cranky, bigoted, obsessive-compulsive writer, finds his life turned upside down when neighboring gay artist Simon is hospitalized and his dog is entrusted to Melvin. In addition, Carol, the only waitress who will tolerate him, must leave work to care for her sick son, making it impossible for Melvin to eat breakfast. (Read More)

Themes:writing, depression, theft, friendship
Locations:restaurant, hospital
Characters:waitress, writer
Story:diner, single mother, road trip, gay slur, bare butt, mother son relationship

Wedding Crashers (2005)
Comedy, Romance

Wedding Crashers (2005)

Two friends, John (played by Owen Wilson) and Jeremy (Vince Vaughn), crash weddings to pick up women. One day they crash the wedding of the daughter of the Treasury Secretary, Secretary Cleary (Christopher Walken). Instead of short-term flings they end up being invited to the Clearys' island estate, and potentially meet the loves of their lives... (Read More)

Themes:divorce, wedding, unfaithfulness, depression, infidelity, marriage, friendship
Locations:beach
Characters:lust
Story:bachelor, cartoon on tv, deceit, engagement, buddy, womanizer, premarital sex, convertible, scantily clad female, gay slur, cleavage, birthday, extramarital affair, bare butt, telephone call, leg spreading, mother son relationship

Clerks II (2006)
Comedy

Clerks II (2006)

A calamity at Dante and Randall's shops sends them looking for new horizons - but they ultimately settle at Mooby's, a fictional fast-food restaurant. Free from his dead-end job (and lodged in a new one), Dante begins to break free of his rut, planning to move away with his clingy fiance. Dante is ready to leave the horrors of minimum-wage New Jersey behind, but Randal - always the more hostile of the two - starts to become overwhelmed by his own rancor. This is why Clerks II (2006) is one of the best movies like Sideways (2004). (Read More)

Themes:drunkenness, infidelity, friendship
Locations:restaurant
Story:fast food, fast food restaurant, bachelor, engagement, convenience store, buddy, scantily clad female, gay slur, cleavage

Catch Me If You Can (2002)
Biography, Crime, Drama

Catch Me If You Can (2002)

New Rochelle, the 1960s. High schooler Frank Abagnale Jr. idolizes his father, who's in trouble with the IRS. When his parents separate, Frank runs away to Manhattan with $25 in his checking account, vowing to regain dad's losses and get his parents back together. Just a few years later, the FBI tracks him down in France; he's extradited, tried, and jailed for passing more than $4,000,000 in bad checks. Along the way, he's posed as a Pan Am pilot, a pediatrician, and an attorney. And, from nearly the beginning of this life of crime, he's been pursued by a dour FBI agent, Carl Hanratty. What starts as cat and mouse becomes something akin to father and son. (Read More)

Themes:divorce, infidelity
Locations:motel, restaurant, hospital
Story:los angeles california, jazz score, wallet, casual sex, divorcee, engagement, unfaithful wife, womanizer, premarital sex, diner, california, extramarital affair, chase, mother son relationship, sex scene

21 Grams (2003) is one of the best movies like Sideways (2004)
Crime, Drama, Thriller

21 Grams (2003)

This is the story of three well-meaning but flawed people: Paul Rivers, an ailing mathematician lovelessly married to an English emigre; Christina Peck, an upper-middle-class suburban housewife, happily married homemaker with two young daughters, with hiding a secret past; and Jack Jordan, an ex-convict who has found in his Christian faith the strength to live a law-abiding life and raise a family. They will be brought together by a terrible accident that will change their lives. By the final frame, none of them will be the same as they will have learnt harsh truths about love, faith, courage, desire and guilt, and how chance can change our worlds irretrievably, forever. (Read More)

Themes:unfaithfulness, drunkenness, infidelity, marriage
Locations:motel, restaurant, hospital
Characters:teacher
Story:golf course, sexual attraction, golf, diner, cleavage, birthday, extramarital affair, sex in bed, car accident, telephone call, mother son relationship, independent film

Thelma & Louise (1991)
Adventure, Crime, Drama

Thelma & Louise (1991)

Louise is working in a diner as a waitress and has some problems with her boyfriend Jimmy, who, as a musician, is always on the road. Thelma is married to Darryl who likes his wife to stay quiet in the kitchen so that he can watch football on TV. One day they decide to break out of their normal life and jump in the car and hit the road. Their journey, however, turns into a flight when Louise kills a man who threatens to rape Thelma. They decide to go to Mexico, but soon they are hunted by American police. (Read More)

Themes:marriage, friendship
Locations:motel
Characters:waitress
Story:highway travel, buddy, convertible, on the road, road movie, diner, road trip, chase

The Wolf Of Wall Street (2013)
Biography, Comedy, Crime, Drama

The Wolf Of Wall Street (2013)

Jordan Belfort is a Long Island penny stockbroker who served 22 months in prison for defrauding investors in a massive 1990s securities scam that involved widespread corruption on Wall Street and in the corporate banking world, including shoe designer Steve Madden.

Themes:unfaithfulness, theft, divorce, wedding, drunkenness, infidelity, marriage, friendship
Mood:satire
Locations:restaurant
Characters:lust, teacher
Story:golf course, crawling, cartoon on tv, no panties, answering machine, golf, single mother, gay slur, marijuana, extramarital affair, bare butt, sex in bed, car accident, telephone call, leg spreading, sex scene

Mulholland Dr. (2001)
Drama, Mystery, Thriller

Mulholland Dr. (2001)

A bright-eyed young actress travels to Hollywood, only to be ensnared in a dark conspiracy involving a woman who was nearly murdered, and now has amnesia because of a car crash. Eventually, both women are pulled into a psychotic illusion involving a dangerous blue box, a director named Adam Kesher, and the mysterious night club Silencio. This is why Mulholland Dr. (2001) is one of the best movies like Sideways (2004). (Read More)

Themes:divorce, infidelity
Characters:waitress
Story:los angeles california, engagement, unfaithful wife, no panties, diner, california, extramarital affair, car accident, telephone call, independent film

Wild Hogs (2007) is one of the best movies like Sideways (2004)
Action, Adventure, Comedy

Wild Hogs (2007)

Four middle-aged men decide to take a road trip from Cincinnati to the Pacific in order to get away from their lives which are leading them nowhere. Taking their motorcycles, these "Wild Hogs" tear up the road and eventually stop in New Mexico for a drink not knowing that the bar belongs to the "Del Fuegos", a mean biker gang. When the Del Fuegos steal a bike that belongs to the Wild Hogs, the four men form a plan to steal their bike back. (Read More)

Themes:divorce, friendship
Locations:hospital
Characters:waitress, writer
Story:road trip, highway travel, midlife crisis, convenience store, on the road, road movie, diner, small town

The Machinist (2004)
Drama, Thriller

The Machinist (2004)

Trevor Reznik is a machinist in a factory. An extreme case of insomnia has led to him not sleeping in a year, and his body withering away to almost nothing. He has an obsessive compulsion to write himself reminder notes and keep track of his dwindling weight, both scribbled on yellow stickies in his apartment. The only person he lets into his life in an emotional sense is Stevie, a prostitute, although he has an infatuation with Maria, a single mother waitress working in an airport diner. His co-workers don't associate with and mistrust him because of not knowing what is going on in his life that has led to his emaciated physical appearance. A workplace incident further alienates him with his coworkers, and in conjunction with some unfamiliar pieces of paper he finds in his apartment, Trevor believes that someone or some people - probably one or some of his coworkers - are out to get him, using a phantom employee named Ivan as their front. As Trevor goes on a search for evidence as to Ivan's schemes and whereabouts, Trevor may come to a true understanding of what has caused his insomnia. (Read More)

Locations:motel
Characters:waitress
Story:los angeles california, copulation, divorcee, coitus, no panties, scantily clad female, diner, single mother, cleavage, sex in bed, car accident, chase, mother son relationship, independent film, sex scene

The Big Lebowski (1998)
Comedy, Crime

The Big Lebowski (1998)

When "The Dude" Lebowski is mistaken for a millionaire Lebowski, two thugs urinate on his rug to coerce him into paying a debt he knows nothing about. While attempting to gain recompense for the ruined rug from his wealthy counterpart, he accepts a one-time job with high pay-off. He enlists the help of his bowling buddy, Walter, a gun-toting Jewish-convert with anger issues. Deception leads to more trouble, and it soon seems that everyone from porn empire tycoons to nihilists want something from The Dude. (Read More)

Themes:divorce, drunkenness, friendship
Mood:satire
Characters:lust, actor
Story:los angeles california, buddy, breaking and entering, no panties, answering machine, premarital sex, convertible, scantily clad female, diner, cleavage, marijuana, bare butt, car accident, telephone call, leg spreading, independent film

Old School (2003)
Comedy

Old School (2003)

Mitch, Frank and Beanie are disillusioned with their personal lives begining when Mitch's nymphomanic girlfriend, Heidi, cheats on him, then former party animal Frank gets married, but unwilling to let go of his wild life, and Beanie is a family man seeking to reclaim his wild and crazy youth. Beanie suggests that they form their own fraternity in Mitch's new house on a college campus to re-live their glory days by bringing together a variety of misfit college students, losers, middle-aged and elderly retirees as their new friends and later try to avoid being evicted by the new Dean of Students, Pritchard, whom still holds a personal grudge against all three of them. (Read More)

Themes:unfaithfulness, divorce, wedding, drunkenness, infidelity, friendship
Story:san diego california, cheating on girlfriend, premarital sex, diner, gay slur, cleavage, car accident, chase

American Psycho (2000) is one of the best movies like Sideways (2004)
Crime, Drama

American Psycho (2000)

Patrick Bateman is handsome, well educated and intelligent. He is twenty-seven and living his own American dream. He works by day on Wall Street, earning a fortune to complement the one he was born with. At night he descends into madness, as he experiments with fear and violence. This is why American Psycho (2000) is one of the best movies like Sideways (2004). (Read More)

Themes:divorce, wedding, drunkenness, infidelity, friendship
Mood:satire
Locations:restaurant
Characters:lust
Story:cityscape, based on novel, answering machine, premarital sex, scantily clad female, wine, gay slur, cleavage, bare butt, sex in bed, car accident, leg spreading, chase, independent film, sex scene

Blue Valentine (2010)
Drama, Romance

Blue Valentine (2010)

Dean Pereira and Cindy Heller Pereira are a young, working class married couple - Dean currently working as a painter, and Cindy working as a nurse in a medical clinic - with a young daughter named Frankie. Despite their relatively tender ages, they are both ravaged by the life they've eked out together and by the experiences they've had leading into their marriage. Dean, a high school drop out, comes from a broken home, where he never really had a mother figure. He never saw himself getting married or having a family despite falling in love at first sight with Cindy. He doesn't have any professional ambition beyond his current work - which he enjoys since he feels he can knock off a beer at 8 o'clock in the morning without it affecting his work - although Cindy believes he has so much more potential in life. Cindy also comes from a dysfunctional family, with her own mother and father not setting an example of a harmonious married or family life. One of her previous serious relationships was with Bobby Ontario, that relationship which has a profound affect on many aspects of her marriage to Dean. Dean and Cindy head off on an overnight getaway together without Frankie, the getaway which may provide a clearer picture if their marriage can survive its many issues. (Read More)

Themes:depression, divorce, wedding, drunkenness, marriage
Locations:motel, restaurant
Characters:lust
Story:wedding ceremony, copulation, coitus, no panties, answering machine, scantily clad female, cleavage, bare butt, telephone call, leg spreading, sex scene

Kiss Kiss Bang Bang (2005)
Comedy, Crime, Mystery

Kiss Kiss Bang Bang (2005)

A petty thief posing as an actor is brought to Los Angeles for an unlikely audition and finds himself in the middle of a murder investigation along with his high school dream girl and a detective who's been training him for his upcoming role...

Themes:theft, drunkenness, friendship
Mood:satire
Locations:motel, beach, hospital
Characters:actor, lust, teacher
Story:los angeles california, based on novel, novel, buddy, breaking and entering, no panties, scantily clad female, gay slur, cleavage, car accident, leg spreading

Road Trip (2000)
Adventure, Comedy

Road Trip (2000)

Josh and Tiffany have been together since they were kids. ENTER Beth, a sexy blonde going to college with Josh. One night, Josh and Beth hook up and make a videotape the same day that Josh plans to mail a video to Tiffany of him talking about college life. The wrong tape gets sent, forcing Josh, along with a few pals, to go to Austin, where Tiffany is, and stop her from seeing the tape. Full of laughs, you'll be sure to enjoy Road Trip. (Read More)

Themes:friendship
Characters:lust
Story:road trip, sex with fat woman, fat girl, highway travel, on the road, road movie, cleavage, marijuana, car accident, interracial sex, sex scene

Forgetting Sarah Marshall (2008) is one of the best movies like Sideways (2004)
Comedy, Drama, Romance

Forgetting Sarah Marshall (2008)

Peter is a composer and a likable sad sack who's devastated when his girlfriend of five years, Sarah Marshall, the star of a cheesy CSI-style crime show, dumps him. He weeps, he rails, he mopes. Finally, his step-brother Brian suggests Hawaii, so Peter heads for a resort on Oahu where, as he's checking in, he sees Sarah and her new beau, Aldous, a polymorphously perverse English rocker. The weeping and moping start again, until Peter is rescued by Rachel, a thoughtful hotel clerk who invites him to a luau and to hang out. Although he constantly runs into Sarah and Aldous, Peter starts to come alive again. Will Sarah realize what she's lost, and what about Rachel? (Read More)

Themes:depression, wedding, drunkenness, infidelity, friendship
Mood:satire
Locations:restaurant, beach
Characters:lust
Story:los angeles california, cheating on girlfriend, no panties, premarital sex, scantily clad female, wine, cleavage, marijuana, bare butt, sex in bed, telephone call, leg spreading, sex scene

The Hangover (2009)
Comedy

The Hangover (2009)

Angelenos Doug Billings and Tracy Garner are about to get married. Two days before the wedding, the four men in the wedding party - Doug, Doug's two best buddies Phil Wenneck and Stu Price, and Tracy's brother Alan Garner - hop into Tracy's father's beloved Mercedes convertible for a 24-hour stag party to Las Vegas. Phil, a married high school teacher, has the same maturity level as his students when he's with his pals. Stu, a dentist, is worried about everything, especially what his controlling girlfriend Melissa thinks. Because she disapproves of traditional male bonding rituals, Stu has to lie to her about the stag, he telling her that they are going on a wine tasting tour in the Napa Valley. Regardless, he intends on eventually marrying her, against the advice and wishes of his friends. And Alan seems to be unaware of what are considered the social graces of the western world. The morning after their arrival in Las Vegas, they awaken in their hotel suite each with the worst hangover. None remembers what happened in the past twelve or so hours. The suite is in shambles. And certain things are in the suite that shouldn't be, and certain things that should be in the suite are missing. Probably the most important in the latter category is Doug. As Phil, Stu and Alan try to find Doug using only what little pieces of information they have at hand, they go on a journey of discovery of how certain things got into the suite and what happened to the missing items. However they are on a race for time as if they can't find Doug in the next few hours, they are going to have to explain to Tracy why they are not yet back in Los Angeles. And even worse, they may not find Doug at all before the wedding. This is why The Hangover (2009) is one of the best movies like Sideways (2004). (Read More)

Themes:wedding, divorce, drunkenness, marriage, friendship
Locations:motel, hospital
Characters:teacher
Story:bachelor, wine tasting, convertible, los angeles california, womanizer, scantily clad female, single mother, wine, road trip, gay slur, cleavage, car accident, leg spreading

A History Of Violence (2005)
Crime, Drama, Thriller

A History Of Violence (2005)

This is the story of a mild-mannered man, named Tom Stall, who becomes a local hero through an act of violence, he lives a happy and quiet life with his lawyer wife and their two children in the small town of Millbrook, Indiana. But one night their idyllic existence is shattered when Tom foils a vicious attempted robbery in his diner. Sensing danger, he takes action and saves his customers and friends in the self-defense killings of two-sought-after criminals. Heralded as a hero, Tom's life is changed overnight, attracting a national media circus, which forces him into the spotlight. Uncomfortable with his newfound celebrity, Tom tries to return to the normalcy of his ordinary life only to be confronted by a mysterious and threatening man who arrives in town believing Tom is the man who wronged him in the past. As Tom and his family fight back against this case of mistaken identity and struggle to cope with their changed reality, they are forced to confront their relationships and the divisive issues which surface as a result. (Read More)

Themes:theft, marriage
Locations:restaurant, hospital
Characters:lust, waitress
Story:diner, crossword puzzle, deceit, scantily clad female, gay slur, cleavage, marijuana, sex in bed, small town, telephone call, leg spreading, mother son relationship, sex scene

Rain Man (1988)
Drama

Rain Man (1988)

Charles Sanford "Charlie" Babbit is a self-centered Los Angeles-based automobile dealer/hustler/bookie who is at war with his own life. Charlie, as a young teenager, used his father's 1949 Buick convertible without permission and as a result, he went to jail for two days on account that his father reported it stolen. It is then that Charlie learns that his estranged father died and left him from his last will and testament a huge bed of roses and the car while the remainder will of $3 Million goes into a trust fund to be distributed to someone. Charlie seemed pretty angry by this and decides to look into this matter. It seems as if that "someone" is Raymond, Charlie's unknown brother, an autistic savant who lives in a world of his own, resides at the Walbrook Institute. Charlie then kidnaps Raymond and decides to take him on a lust for life trip to the west coast as a threat to get the $3 Million inheritance. Raymond's acts and nagging, including repeated talks of "Abbott & Costello", "Four minutes till Wapner" and refusal to fly on an airline except Quantas drives Charlie insane... and out of his selfish world into a cross-country trek of pure love and understanding that these two both have. (Read More)

Locations:motel
Characters:lust, waitress
Story:convertible, coitus, caught having sex, premarital sex, on the road, road movie, diner, california, road trip, sex in bed, small town, telephone call, sex scene

Crazy, Stupid, Love. (2011) is one of the best movies like Sideways (2004)
Comedy, Drama, Romance

Crazy, Stupid, Love. (2011)

Cal (Steve Carell) and Emily (Julianne Moore) have the perfect life together living the American dream... until Emily asks for a divorce. Now Cal, Mr Husband, has to navigate the single scene with a little help from his professional bachelor friend Jacob Palmer (Ryan Gosling). Make that a lot of help... (Read More)

Themes:divorce, unfaithfulness, depression, drunkenness, infidelity, marriage, friendship
Characters:teacher
Story:los angeles california, bachelor, wallet, midlife crisis, buddy, womanizer, answering machine, extramarital affair, telephone call, chase, mother son relationship, sex scene

The Invention Of Lying (2009)
Comedy, Fantasy, Romance

The Invention Of Lying (2009)

It's a world where everyone tells the truth - and just about anything they're thinking. Mark Bellison is a screenwriter, about to be fired. He's short and chunky with a flat nose - a genetic setup that means he won't get to first base with Anna, the woman he loves. At a bank, on the spur of the moment he blurts out a fib, with eye-popping results. Then, when his mother's on her deathbed, frightened of the eternal void awaiting her, Mark invents fiction. The hospital staff overhear his description of Heaven, believe every word, and tell others. Soon Mark is a prophet, his first inventive screenplay makes him rich, and he's basically a good guy. But will that be enough for Anna? (Read More)

Themes:writing, depression, theft, wedding, drunkenness, marriage, friendship
Mood:satire
Locations:motel, restaurant, hospital
Characters:waitress, writer
Story:wedding ceremony, deceit, breaking and entering, gay slur, birthday, small town, telephone call, mother son relationship

I Love You, Man (2009)
Comedy, Romance

I Love You, Man (2009)

Peter Klaven's world revolves around his real estate work and Zooey, his soon-to-be fiancee. After he pops the question, she calls her best friends and they go into wedding planning mode. Peter has no male friends and that poses problems: will he turn out to be a clingy guy, and who will be his best man? Zooey, her friends, and Peter's brother Robbie offer help that results in awkward moments. Then, at an open house Peter's hosting, he meets Sydney, an amiable, low-key guy. They trade business cards, and Peter calls him to meet for drinks. A friendship develops that's great at first but then threatens Peter's engagement and career. Can guys be friends and couples be in love? This is why I Love You, Man (2009) is one of the best movies like Sideways (2004). (Read More)

Themes:wedding, drunkenness, marriage, friendship
Locations:restaurant, beach
Story:golf course, los angeles california, divorcee, engagement, buddy, golf, wine, guitar, marijuana, telephone call, mother son relationship

No Strings Attached (2011)
Comedy, Romance

No Strings Attached (2011)

Occasionally in the 15 years since summer camp, Adam and Emma cross paths. When he discovers that an ex-girlfriend is living with his dad, he gets drunk, calls every woman in his cell phone contact list, and ends up passed out naked in her living room. By this time, she's a medical resident in L.A. and he's a gopher on a "Glee"-like TV series, hoping to be a writer. She guards her emotions (calling her father's funeral "a thing"), so after a quick shag in the moments she has before leaving for the hospital, she asks if he wants a no-strings-attached, sex-only relationship, without romance or complications. A prescription for fun or for disaster? (Read More)

Themes:divorce, drunkenness
Locations:restaurant, hospital
Characters:writer, waitress, actor
Story:los angeles california, engagement, sexual attraction, diner, guitar, marijuana, birthday, bare butt, sex scene

Boogie Nights (1997) is one of the best movies like Sideways (2004)
Drama

Boogie Nights (1997)

Adult film director Jack Horner is always on the lookout for new talent and it's only by chance that he meets Eddie Adams who is working as a busboy in a restaurant. Eddie is young, good looking and plenty of libido to spare. Using the screen name Dirk Diggler, he quickly rises to the top of his industry winning awards year after year. Drugs and ego however come between Dirk and those around him and he soon finds that fame is fleeting. (Read More)

Themes:marriage
Locations:motel, restaurant, hospital
Characters:actor
Story:los angeles california, copulation, casual sex, divorcee, coitus, no panties, scantily clad female, diner, california, gay slur, cleavage, guitar, sex in bed, telephone call, mother son relationship, independent film

One Hour Photo (2002)
Drama, Thriller

One Hour Photo (2002)

Middle aged Sy Parrish works as a technician at a one hour photo lab located in a SavMart store in a suburban mall. Sy is a lonely man, never having had any friends. He knows much about his customers through the photographs they have developed. But he knows more about the Yorkin family - specifically Nina Yorkin and her adolescent son Jake Yorkin, the two in the family who drop off and pick up the family's photofinishing - the family about whom he is obsessed, than anyone else. Nina's husband, Will Yorkin, is incidental to his obsession since Sy has only seen him in photographs. Sy's obsession includes fantasizing about being their favorite "Uncle Sy". He has even been making an extra set of prints for himself of all of their photographs since Jake was a newborn. After an incident at work and after Sy finds out more about the family through a set of photographs, he decides to right the injustices he sees in the only way he knows how. His actions demonstrate his true mental state. (Read More)

Themes:unfaithfulness, depression, theft, drunkenness, infidelity, marriage
Locations:restaurant
Characters:waitress
Story:cartoon on tv, breaking and entering, no panties, scantily clad female, diner, cleavage, birthday, extramarital affair, car accident, mother son relationship

The Lost Boys (1987)
Comedy, Horror

The Lost Boys (1987)

A mother and her two sons move to a small coast town in California. The town is plagued by bikers and some mysterious deaths. The younger boy makes friends with two other boys who claim to be vampire hunters while the older boy is drawn into the gang of bikers by a beautiful girl. The older boy starts sleeping days and staying out all night while the younger boy starts getting into trouble because of his friends' obsession. (Read More)

Locations:beach
Story:california, divorcee, small town, premarital sex, convertible, single mother, wine, marijuana, chase, mother son relationship

Fargo (1996)
Crime, Drama, Thriller

Fargo (1996)

Jerry works in his father-in-law's car dealership and has gotten himself in financial problems. He tries various schemes to come up with money needed for a reason that is never really explained. It has to be assumed that his huge embezzlement of money from the dealership is about to be discovered by father-in-law. When all else falls through, plans he set in motion earlier for two men to kidnap his wife for ransom to be paid by her wealthy father (who doesn't seem to have the time of day for son-in-law). From the moment of the kidnapping, things go wrong and what was supposed to be a non-violent affair turns bloody with more blood added by the minute. Jerry is upset at the bloodshed, which turns loose a pregnant sheriff from Brainerd, MN who is tenacious in attempting to solve the three murders in her jurisdiction. This is why Fargo (1996) is one of the best movies like Sideways (2004). (Read More)

Themes:marriage
Mood:satire
Locations:motel, restaurant
Story:fast food, copulation, deceit, buddy, coitus, breaking and entering, no panties, scantily clad female, diner, cleavage, sex in bed, small town, car accident, mother son relationship, independent film, one word title, sex scene

Due Date (2010) is one of the best movies like Sideways (2004)
Comedy, Drama

Due Date (2010)

In Atlanta on business, straight-laced and overly analytical architect Peter Highman is flying home to Los Angeles and his wife Sarah for the imminent birth of their first child. However, traveling by plane no longer becomes an option when he and a fellow passenger, aspiring actor Ethan Tremblay, are kicked off the plane, which was caused by Ethan's social inappropriateness, due to being generally unaware, exacerbated by Peter's temper at a situation against his sensibilities. Peter, who ends up without money or his suitcase, is forced to accept Ethan's offer of a shared car ride to Los Angeles, Ethan who is looking for his big acting break. For Peter, this partnership is one made in hell, but he feels he has no other choice. Peter obviously wants to take as direct and as quick a route as possible, while he is at Ethan's mercy as the person with the driver's license, car rental and money. They get into one misadventure after another on this trip, with the same issue at each misadventure being Ethan's ineptness as an adult combined with Peter's resulting temper. The questions become whether they will survive the trip together, and if so if Peter will make it home in time to witness the birth of his and Sarah's first child. (Read More)

Themes:friendship
Locations:motel, restaurant, hospital
Characters:actor
Story:los angeles california, highway travel, wallet, cartoon on tv, buddy, on the road, diner, single mother, road trip, marijuana, car accident, mother son relationship

The Hours (2002)
Drama, Romance

The Hours (2002)

In 1951, Laura Brown, a pregnant housewife, is planning a party for her husband, but she can't stop reading the novel 'Mrs. Dalloway'. Clarissa Vaughn, a modern woman living in present times is throwing a party for her friend Richard, a famous author dying of AIDS. These two stories are simultaneously linked to the work and life of Virginia Woolf, who's writing the novel mentioned before. (Read More)

Themes:writing, depression, friendship
Characters:writer
Story:author, birthday, los angeles california, middle age romance, based on novel, novel, melancholy, medication, single mother, mother son relationship

Jay And Silent Bob Strike Back (2001)
Comedy

Jay And Silent Bob Strike Back (2001)

Jay and Silent Bob Strike Back is a tale of adventure on the open road. When Dante and Randal (of Clerks fame) get a restraining order to keep the punchy Jay and his hetero life-mate, Silent Bob, from selling drugs in front of the Quick Stop convenience store, their lives are suddenly empty. They find new purpose when their friend, Brodie, informs them a movie is being made featuring two infamous characters based on their likenesses. After visiting one of the creators of the Bluntman and Chronic, Holden McNeil, they set out to get what fat movie cash they deserve and hopefully put an end to people slandering them on the Internet. Along the way, they learn the rules of the road from a hitchhiking George Carlin, ride with a group of gorgeous jewel thieves, and incur the wrath of a hapless wildlife marshal for liberating an orangutan named Suzanne. The quest takes them from New Jersey to Hollywood where a showdown involving the police, the jewel thieves, and the Bluntman and Chronic filmmakers will decide the fate of Suzanne, Jay, Silent Bob, and their good names. (Read More)

Mood:satire
Story:highway travel, convenience store, on the road, road movie, scantily clad female, california, road trip, gay slur, cleavage, guitar, chase, independent film

Ray (2004)
Biography, Drama, Music

Ray (2004)

The story of Ray Charles, music legend. Told in his adult live with flashbacks to his youth we see his humble origins in Florida, his turbulent childhood which included losing his brother and then his sight, his rise as pianist in a touring band, his writing his own songs and running his own band and then stardom. Also includes his addiction to drugs and its affect on his working life and family life. (Read More)

Themes:writing, unfaithfulness, wedding, drunkenness, infidelity, marriage
Locations:beach, hospital
Story:los angeles california, premarital sex, single mother, guitar, marijuana, birthday, extramarital affair, mother son relationship, one word title

The School Of Rock (2003) is one of the best movies like Sideways (2004)
Comedy, Family, Music

The School Of Rock (2003)

Down and out rock star Dewey Finn gets fired from his band, and he faces a mountain of debts and depression. He takes a job as a 4th grade substitute teacher at an uptight private school where his attitude and hijinx have a powerful effect on his students. He also meets Zack, a 10-year-old guitar prodigy, who could help Dewey win a "battle of the bands" competition, which would solve his financial problems and put him back in the spotlight. This is why The School Of Rock (2003) is one of the best movies like Sideways (2004). (Read More)

Themes:depression, drunkenness, friendship
Characters:teacher
Story:guitar, los angeles california, deceit, diner, small town, telephone call

Eyes Wide Shut (1999)
Drama, Mystery, Thriller

Eyes Wide Shut (1999)

After his wife, Alice, tells him about her sexual fantasies, William Harford sets out for a night of sexual adventure. After several less than successful encounters, he meets an old friend, Nick Nightingale - now a musician - who tells him of strange sex parties when he is required to play the piano blindfolded. All the men at the party are costumed and wear masks while the women are all young and beautiful. Harford manages to find an appropriate costume and heads out to the party. Once there, however, he is warned by someone who recognizes him, despite the mask, that he is in great danger. He manages to extricate himself but the threats prove to be quite real and sinister. (Read More)

Themes:drunkenness, infidelity, marriage, friendship
Locations:restaurant
Characters:lust, waitress
Story:based on novel, cartoon on tv, copulation, deceit, coitus, sexual attraction, no panties, scantily clad female, cleavage, marijuana, extramarital affair, telephone call, leg spreading

Blow (2001)
Biography, Crime, Drama

Blow (2001)

A boy named George Jung grows up in a struggling family in the 1950's. His mother nags at her husband as he is trying to make a living for the family. It is finally revealed that George's father cannot make a living and the family goes bankrupt. George does not want the same thing to happen to him, and his friend Tuna, in the 1960's, suggests that he deal marijuana. He is a big hit in California in the 1960's, yet he goes to jail, where he finds out about the wonders of cocaine. As a result, when released, he gets rich by bringing cocaine to America. However, he soon pays the price. (Read More)

Themes:theft, divorce, wedding, marriage, friendship
Locations:beach
Characters:actor
Story:california, los angeles california, gay slur, marijuana, birthday, mother son relationship, one word title

Basic Instinct (1992)
Drama, Mystery, Thriller

Basic Instinct (1992)

A former rock star, Johnny Boz, is brutally killed during sex, and the case is assigned to detective Nick Curran of the SFPD. During the investigation, Nick meets Catherine Tramell, a crime novelist who was Boz's girlfriend when he died. Catherine proves to be a very clever and manipulative woman, and though Nick is more or less convinced that she murdered Boz, he is unable to find any evidence. Later, when Nilsen, Nick's rival in the police, is killed, Nick suspects of Catherine's involvement in it. He then starts to play a dangerous lust-filled mind game with Catherine to nail her, but as their relationship progresses, the body count rises and contradicting evidences force Nick to start questioning his own suspicions about Catherine's guilt. (Read More)

Themes:writing, unfaithfulness, drunkenness
Characters:lust, writer
Story:novel, deceit, sexual attraction, no panties, author, scantily clad female, california, cleavage, sex in bed, leg spreading, chase, sex scene

Leaving Las Vegas (1995) is one of the best movies like Sideways (2004)
Drama, Romance

Leaving Las Vegas (1995)

Because his wife left him and took his son with her, screenwriter Ben Sanderson has started drinking, a lot. He's getting more and more isolated and he troubles women in bars because he wants to have sex with them. When he gets fired, he decides to leave everything behind and move to Las Vegas and drink himself to death. In Las Vegas he meets Sera, a prostitute with some problems as well who he moves in with. (Read More)

Themes:depression, theft, infidelity
Locations:motel, restaurant
Story:los angeles california, jazz score, based on novel, no panties, scantily clad female, cleavage, sex in bed

Knocked Up (2007)
Comedy, Romance

Knocked Up (2007)

When Alison Scott is promoted in E! Television, she goes to a night-club to celebrate with her older married sister Debbie. Alison meets the pothead reckless Ben Stone and while having a small talk with Ben, Debbie's husband Pete calls her to tell that their daughter has chicken pox. Debbie leaves the place but Allison stays with Ben, drinking and dancing along all night; completely wasted, they end up having a one night stand. Ben does not use condom and eight weeks later, Allison discovers that she is pregnant. She calls Ben and they decide to try to stay together and have the baby. However, Ben needs to grow-up first to raise a family of his own. This is why Knocked Up (2007) is one of the best movies like Sideways (2004). (Read More)

Themes:drunkenness, infidelity, marriage
Locations:restaurant, hospital
Characters:lust
Story:los angeles california, casual sex, premarital sex, scantily clad female, diner, gay slur, cleavage, marijuana, bare butt, sex in bed, sex scene

Harold & Kumar Go To White Castle (2004)
Adventure, Comedy

Harold & Kumar Go To White Castle (2004)

Harold Lee and Kumar Patel are two stoners who end up getting the munchies. What they crave the most after seeing a TV advertisement, is a trip to White Castle. So from here, follows a journey for the burgers they require. On their way they will encounter many obstacles including a raccoon, a racist officer, and a horny Neil Patrick Harris. (Read More)

Themes:friendship
Locations:restaurant, hospital
Story:highway travel, fast food, sexual attraction, convertible, on the road, road movie, scantily clad female, road trip, cleavage, marijuana, bare butt, car accident, sex scene

Manhattan (1979)
Comedy, Drama, Romance

Manhattan (1979)

Forty-two year old Isaac Davis has a romanticized view of his hometown, New York City, most specifically Manhattan, as channeled through the lead character in the first book he is writing, despite his own Manhattan-based life being more of a tragicomedy. He has just quit his job as a hack writer for a bad television comedy, he, beyond the ten second rush of endorphins during the actual act of quitting, now regretting the decision, especially as he isn't sure he can live off his book writing career. He is paying two alimonies, his second ex-wife, Jill Davis, a lesbian, who is writing her own tell-all book of their acrimonious split. The one somewhat positive aspect of his life is that he is dating a young woman named Tracy, although she is only seventeen and still in high school. Largely because of their differences a big part of which is due to their ages, he does not see a long term future with her. His life has the potential to be even more tragicomical when he meets journalist Mary Wilkie, the mistress of his best friend, college professor Yale Pollack. Although Isaac's first impression of Mary is that she is a pretentious intellectual, he falls for her. They do become friends with the potential of becoming more than just friends as she knows that being the "other woman" in Yale's life is not a long term role that she wants. An Isaac/Mary coupling may complicate matters even more with Yale being mutually in their lives. Regardless, Isaac may be able to rationalize events after they happen, no matter what those events are. (Read More)

Themes:writing, divorce, marriage
Mood:satire
Locations:restaurant
Characters:writer, teacher
Story:novel, premarital sex, convertible, diner, extramarital affair, telephone call, one word title

I Am Sam (2001) is one of the best movies like Sideways (2004)
Drama

I Am Sam (2001)

Sam Dawson has the mental capacity of a 7-year-old. He works at a Starbucks and is obsessed with the Beatles. He has a daughter with a homeless woman; she abandons them as soon as they leave the hospital. He names his daughter Lucy Diamond (after the Beatles song), and raises her. But as she reaches age 7 herself, Sam's limitations start to become a problem at school; she's intentionally holding back to avoid looking smarter than him. The authorities take her away, and Sam shames high-priced lawyer Rita Harrison into taking his case pro bono. In the process, he teaches her a great deal about love, and whether it's really all you need. (Read More)

Themes:divorce, friendship
Locations:restaurant, hospital
Characters:teacher
Story:los angeles california, cartoon on tv, answering machine, california, single mother, birthday, mother son relationship

Sex And The City (2008)
Comedy, Drama, Romance

Sex And The City (2008)

After moving in together in an impossibly beautiful New York apartment, Carrie Bradshaw and Mr. Big make a rather arbitrary decision to get married. The wedding itself proves to be anything but a hasty affair--the guest list quickly blooms from 75 to 200 guests, and Carrie's simple, label-less wedding gown gives way to an enormous creation that makes her look like a gigantic cream puff. An upcoming photo spread in Vogue puts the event--which will take place at the New York Public Library--squarely in the public eye. Meanwhile, Carrie's girlfriends--Samantha, the sexpot; Charlotte, the sweet naif; and Miranda, the rigid perfectionist--could not be happier. At least, they couldn't be happier for Carrie. Charlotte still has the unrealized hope of getting pregnant. Samantha is finding a loving, committed relationship more grueling than she could have imagined. Miranda unwittingly lets her own unhappiness--created when Steve admits to cheating on her just once--spoil Carrie's. After a heated encounter with Steve, she happens to spot Mr. Big and tells him he's crazy to get married. She's really only thinking of her own marriage. But her angry remark gets Mr. Big to thinking. (Read More)

Themes:wedding, depression, marriage, friendship
Locations:hospital
Characters:lust, writer, actor
Story:los angeles california, voice mail, copulation, coitus, no panties, scantily clad female, cleavage, sex in bed, leg spreading, sex scene

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