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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,  winery,  cheating on girlfriend,  has been,  reference to ernest hemingway,  grape,  fat girl,  voice mail,  crawling,  highway travel,  self doubt,  crossword puzzle,  ostrich,  cityscape,  junior high school,  vineyard,  middle age,  broken nose,  failure,  windmill,  based on novel,  fast food,  bachelor,  wallet,  cartoon on tv,  novel,  man crying,  midlife crisis,  melancholy,  copulation,  casual sex,  divorcee,  deceit,  engagement,  convenience store,  medication,  unfaithful wife,  buddy,  crying man,  womanizer,  coitus,  caught having sex,  sexual attraction,  breaking and entering,  no panties,  answering machine,  golf,  premarital sex,  convertible,  on the road,  road movie,  author,  scantily clad female,  diner,  california,  single mother,  gay slur,  cleavage,  guitar,  marijuana,  birthday,  extramarital affair,  bare butt,  sex in bed,  small town,  car accident,  telephone call,  leg spreading,  chase,  interracial sex,  mother son relationship,  independent film,  one word title,  sex scene

Short Cuts (1993)
Comedy, Drama

Short Cuts (1993)

While helicopters overhead spray against a Medfly infestation a group of Los Angeles lives intersect, some casually, some to more lasting effect. Whilst they go out to concerts and jazz clubs and even have their pools cleaned, they also lie, drink, and cheat. Death itself seems never to be far away, even on a fishing trip. (Read More)

Themes:unfaithfulness,  drunkenness,  infidelity,  marriage,  friendship
Locations:hospital
Characters:lust,  waitress
Story:los angeles california,  jazz score,  melancholy,  unfaithful wife,  no panties,  scantily clad female,  california,  cleavage,  marijuana,  birthday,  extramarital affair,  bare butt,  sex in bed,  car accident,  telephone call,  mother son relationship,  independent film

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Nurse Betty (2000)
Comedy, Crime, Drama, Romance

Nurse Betty (2000)

A Kansas City waitress with dreams of becoming a nurse becomes delusional after seeing her no-good car salesman husband murdered. Becoming delusional from shock, she becomes convinced that she is the former fiancee of her soap opera idol. What she also believes is that the soap opera is real and goes to LA to find the hospital where he works as a cardiologist. Meanwhile, her husband's murderers are searching for the drugs stolen by her husband and, as luck would have it, they are stored in the trunk of the car she drove off in. Freeman, an aging hit man planning his retirement after this job, also becomes delusional about the woman he is tracking. (Read More)

Themes:theft,  infidelity,  friendship
Mood:satire
Locations:motel,  restaurant,  hospital
Characters:waitress,  writer,  actor
Story:los angeles california,  highway travel,  crying man,  on the road,  road movie,  diner,  road trip,  gay slur,  birthday,  small town,  car accident,  telephone call,  chase,  independent film

Spread (2009)
Comedy, Drama, Romance

Spread (2009)

In Los Angeles, Nikki is homeless, car-less and closing in on 30, but he's amoral, good-looking, and adept in the sack, moving from one wealthy woman of 35 or 40 to another, a kept boy-toy. His newest gig, with Samantha, an attorney whose house overlooks L.A., is sweet, although it's unclear how long she'll put up with him. Then Nikki meets Heather, a waitress. Is the player being played, or might this be love? What will Nikki discover? (Read More)

Themes:unfaithfulness,  drunkenness,  infidelity
Characters:lust,  waitress
Story:unfaithful wife,  womanizer,  caught having sex,  sexual attraction,  scantily clad female,  diner,  cleavage,  extramarital affair,  sex in bed,  telephone call,  leg spreading,  one word title,  sex scene

Swingers (1996) is one of the best movies like Sideways (2004)
Comedy, Drama

Swingers (1996)

This is a story about Mike, a guy who left his girl in New York when he came to LA to be a star. It's been six months since his girlfriend left him and he's not doing so good. So, his pal and some other friends try and get him back in the social scene and forget about his 6 year relationship.

Themes:depression,  drunkenness,  friendship
Locations:restaurant
Characters:waitress,  actor
Story:golf course,  los angeles california,  womanizer,  answering machine,  golf,  premarital sex,  on the road,  scantily clad female,  diner,  gay slur,  cleavage,  telephone call,  independent film,  one word title

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Adoration (2013)
Drama, Romance

Adoration (2013)

Lil ('Naomi Watts' (qv)) and Roz ('Robin Wright (V)' (qv)) are two lifelong friends, having grown up together as neighbors in an idyllic beach town. As adults, their sons have developed a friendship as strong as that which binds their mothers. One summer, all four are confronted by simmering emotions that have been mounting between them, and each find unexpected happiness in relationships that cross the bounds of convention. This is why Adoration (2013) is one of the best movies like Sideways (2004). (Read More)

Themes:unfaithfulness,  divorce,  wedding,  drunkenness,  infidelity,  marriage,  friendship
Locations:beach,  hospital
Characters:actor
Story:copulation,  coitus,  scantily clad female,  wine,  cleavage,  birthday,  extramarital affair,  bare butt,  sex in bed,  telephone call,  leg spreading,  mother son relationship

The Last Kiss (2006)
Comedy, Drama, Romance

The Last Kiss (2006)

Michael and Jenna, having been a couple for three years, want to get married and start a family. These plans seem to be well on their way when Jenna announces that she's pregnant. But Michael is worried that his life and his youth will be over for good. At a wedding of a friend, he meets a free-spirited college co-ed, Kim, who opens his eyes and leads him on a dangerous path away from Jenna. Meanwhile, none of the relationships of the people surrounding Michael and Jenna are happy and stable. Michael's friend Izzy is unwilling to let go of his childhood sweetheart Arianna; Kenny is a handsome stud who fears commitment to his latest conquest Danielle; and Chris is a co-worker who is dominated by his neurotic and overbearing wife over raising their newborn son. Even Jenna's parents, Stephen and Anna, are experiencing problems in their long-suffering marriage. (Read More)

Themes:unfaithfulness,  wedding,  drunkenness,  infidelity,  marriage,  friendship
Characters:lust
Story:midlife crisis,  casual sex,  scantily clad female,  wine,  cleavage,  marijuana,  extramarital affair,  bare butt,  sex in bed,  car accident,  telephone call,  leg spreading,  mother son relationship

Broken Flowers (2005)
Comedy, Drama, Mystery, Romance

Broken Flowers (2005)

The resolutely single Don Johnston has just been dumped by his latest lover, Sherry. Don resigns himself to being alone yet again and left to his own devices. Instead, he is compelled to reflect on his past when he receives by mail a mysterious pink letter. It is from an anonymous former lover and informs him that he has a 19-year-old son who may now be looking for his father. Don is urged to investigate this "mystery" by his closest friend and neighbor, Winston, an amateur sleuth and family man. Hesitant to travel at all, Don nonetheless embarks on a cross-country trek in search of clues from four former flames. Unannounced visits to each of these unique women hold new surprises for Don as he haphazardly confronts both his past and, consequently, his present. (Read More)

Themes:divorce,  marriage,  friendship
Locations:motel
Characters:waitress,  writer
Story:knocking on door,  highway travel,  bachelor,  casual sex,  womanizer,  no panties,  on the road,  road movie,  author,  scantily clad female,  road trip,  marijuana,  car accident,  mother son relationship

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About Schmidt (2002) is one of the best movies like Sideways (2004)
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

Lucia Y El Sexo (2001)
Drama, Romance

Lucia Y El Sexo (2001)

Lucia is a young waitress in a restaurant in the centre of Madrid. After the loss of her long-time boyfriend, a writer, she seeks refuge on a quiet, secluded Mediterranean island. There, bathed in an atmosphere of fresh air and dazzling sun, Lucia begins to discover the dark corners of her past relationship, as if they were forbidden passages of a novel which the author now, from afar, allows her to read. (Read More)

Themes:depression,  drunkenness,  infidelity,  friendship
Locations:restaurant,  beach,  hospital
Characters:waitress,  writer,  lust
Story:novel,  copulation,  no panties,  author,  scantily clad female,  cleavage,  birthday,  sex in bed,  car accident,  telephone call,  leg spreading,  sex scene

Intolerable Cruelty (2003)
Comedy, Crime, Romance

Intolerable Cruelty (2003)

Miles Massey, a prominent Los Angeles divorce attorney has everything--and in some cases, two of everything. Despite his impressive client list, a formidable win record, the respect of his peers and an ironclad contract (the Massey pre-nup) named after him, he's reached a crossroads in his life. Sated on success, boredom has set in and he's looking for new challenges. All that changes when Miles meets his match in the devastating Marylin Rexroth. Marylin is the soon-to-be ex-wife of his client Rex Rexroth, a wealthy real estate developer and habitual philanderer. With the help of hard charging private investigator Gus Petch, she has Rex nailed and is looking forward to the financial independence a successful divorce will bring. But thanks to Miles' considerable skills, she ends up with nothing. Not to be outdone, Marylin schemes to get even and as part of her plan, quickly marries oil tycoon Howard Doyle. Miles and his unflappable associate, Wrigley, unwittingly dig themselves in deeper and deeper as they go head-to-head with Marylin. Underhanded tactics, deceptions and an undeniable attraction escalate as Marylin and Miles square off in this classic battle of the sexes. This is why Intolerable Cruelty (2003) is one of the best movies like Sideways (2004). (Read More)

Themes:divorce,  unfaithfulness,  wedding,  infidelity,  marriage,  friendship
Mood:satire
Locations:motel,  restaurant
Characters:waitress,  actor
Story:los angeles california,  midlife crisis,  deceit,  breaking and entering,  convertible,  diner,  wine,  guitar,  extramarital affair,  car accident

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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

Y Tu Mama Tambien (2001) is one of the best movies like Sideways (2004)
Adventure, Comedy, Drama, Romance

Y Tu Mama Tambien (2001)

In Mexico City, late teen friends Tenoch Iturbide and Julio Zapata are feeling restless as their respective girlfriends are traveling together through Europe before they all begin the next phase of their lives at college. At a lavish family wedding, Tenoch and Julio meet Luisa Cortes, the twenty-something wife of Tenoch's cousin Jano, the two who have just moved to Mexico from Spain. Tenoch and Julio try to impress the beautiful Luisa by telling her that they will be taking a trip to the most beautiful secluded beach in Mexico called la Boca del Cielo (translated to Heaven's Mouth), the trip and the beach which in reality don't exist. When Luisa learns of Jano's latest marital indiscretion straight from the horse's mouth, she takes Tenoch and Julio's offer to go along on this road trip, meaning that Tenoch and Julio have to pull together quickly a road trip to a non-existent beach. They decide to head toward one suggested by their friend Saba, who seems a little confused himself of this beach's location. On the road trip, which ends up not being totally harmonious, the three go on a trip of discovery. For Luisa, she has to figure out what to do with her immediate future based on the news from Jano and a secret she is keeping. And Tenoch and Julio have to figure out what their friendship really means as they grow up. (Read More)

Themes:wedding,  unfaithfulness,  divorce,  drunkenness,  infidelity,  marriage,  friendship
Locations:beach,  restaurant
Characters:lust,  writer
Story:road trip,  coitus,  sexual attraction,  no panties,  answering machine,  on the road,  road movie,  gay slur,  cleavage,  marijuana,  extramarital affair,  bare butt,  telephone call,  leg spreading,  mother son relationship,  independent film

Fast Times At Ridgemont High (1982)
Comedy, Drama

Fast Times At Ridgemont High (1982)

Follows a group of high school students growing up in southern California, based on the real-life adventures chronicled by Cameron Crowe. Stacy Hamilton and Mark Ratner are looking for a love interest, and are helped along by their older classmates, Linda Barrett and Mike Damone, respectively. The center of the film is held by Jeff Spicoli, a perpetually stoned surfer dude who faces off with the resolute Mr. Hand, who is convinced that everyone is on dope. (Read More)

Themes:friendship
Locations:restaurant,  hospital
Characters:teacher,  lust
Story:california,  los angeles california,  fast food restaurant,  fast food,  convenience store,  sexual attraction,  premarital sex,  scantily clad female,  gay slur,  cleavage,  marijuana,  car accident,  leg spreading,  sex scene

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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

The Good Girl (2002)
Drama, Romance

The Good Girl (2002)

The plot revolves around a young married woman whose mundane life takes a turn for the worse when she strikes up a passionate and illicit affair with an oddball discount-store stock boy who thinks he's Holden Caulfield. This is why The Good Girl (2002) is one of the best movies like Sideways (2004).

Themes:unfaithfulness,  depression,  theft,  drunkenness,  infidelity,  marriage,  friendship
Locations:motel,  hospital
Characters:writer
Story:cartoon on tv,  marijuana,  extramarital affair,  bare butt,  sex in bed,  small town,  mother son relationship,  independent film,  sex scene

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

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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. (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

The Unbearable Lightness Of Being (1988)
Drama, Romance

The Unbearable Lightness Of Being (1988)

Tomas is a doctor and a lady-killer in 1960s Czechoslovakia, an apolitical man who is struck with love for the bookish country girl Tereza; his more sophisticated sometime lover Sabina eventually accepts their relationship and the two women form an electric friendship. The three are caught up in the events of the Prague Spring (1968), until the Soviet tanks crush the non-violent rebels; their illusions are shattered and their lives change forever. (Read More)

Themes:unfaithfulness,  wedding,  infidelity,  marriage,  friendship
Locations:restaurant,  beach,  hospital
Characters:waitress,  writer
Story:based on novel,  womanizer,  no panties,  scantily clad female,  california,  wine,  cleavage,  extramarital affair,  sex in bed,  leg spreading,  independent film

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Lolita (1997) is one of the best movies like Sideways (2004)
Drama, Romance

Lolita (1997)

Humbert Humbert, a British professor coming to the US to teach, rents a room in Charlotte Haze's house, but only after he sees her 14-year-old daughter, Dolores (Lolita), to whom he is immediately attracted. Though he hates the mother, he marries her as this is the only way to be close to the girl, who will prove to be too mature for her age. They start a journey together, trying to hide they're not just (step)father and daughter, throughout the country, being followed by someone whom Humbert first suspects to be from the police. The profound jealousy, and maybe some guilt from the forbidden love, seem slowly to drive the man emotionally labile. This is why Lolita (1997) is one of the best movies like Sideways (2004). (Read More)

Themes:writing,  drunkenness,  marriage
Locations:motel,  hospital
Characters:lust,  writer,  teacher
Story:based on novel,  copulation,  coitus,  sexual attraction,  scantily clad female,  road trip,  cleavage,  sex in bed,  car accident,  telephone call,  leg spreading,  independent film

Sleeping With Other People (2015)
Comedy, Drama, Romance

Sleeping With Other People (2015)

Themes:unfaithfulness,  infidelity,  marriage,  friendship
Locations:restaurant,  hospital
Characters:teacher
Story:copulation,  divorcee,  womanizer,  coitus,  answering machine,  scantily clad female,  wine,  cleavage,  marijuana,  extramarital affair,  telephone call,  chase,  interracial sex,  mother son relationship

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

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Alfie (2004)
Comedy, Drama, Romance

Alfie (2004)

In Manhattan, the British limousine driver Alfie is surrounded by beautiful women, most of them clients, and he lives as a Don Juan, having one night stands with all of them and without any sort of commitment. His girl-friend and single-mother Julie is quite upset with the situation and his best friends are his colleague Marlon and his girl-friend Lonette. Alfie has a brief affair with Lonette, and the consequences of his act forces Alfie to reflect and wonder about his life style. (Read More)

Themes:unfaithfulness,  drunkenness,  infidelity,  marriage,  friendship
Locations:restaurant,  beach
Story:cheating on girlfriend,  casual sex,  unfaithful wife,  womanizer,  premarital sex,  scantily clad female,  single mother,  cleavage,  marijuana,  extramarital affair,  interracial sex,  mother son relationship,  one word title,  sex scene

The Heartbreak Kid (2007) is one of the best movies like Sideways (2004)
Comedy, Romance

The Heartbreak Kid (2007)

Eddie is forty, owns a sporting-goods store, and is still single. After watching his ex-fiancee walk down the aisle, he meets Lila, an environmental researcher, who seems too good to be true. Pressured by his father and best friend, Eddie pops the question and marries Lila after only 6 weeks. However, as he almost instantly discovers, his new bride is a nightmare with more baggage than he can handle. She's immature, foolish, a monster in bed, owes a tremendous amount of money to various sources, and as it turns out, is only a volunteer and doesn't actually have a job. While on their honeymoon in Cabo, Eddie meets Miranda, a down-to-earth lacrosse coach who is visiting with her family. Sparks fly, and Eddie falls for her. Now comes the tricky part of breaking off his marriage to crazy Lila, all while keeping the truth from Miranda about why he's in Cabo in the first place... (Read More)

Themes:divorce,  wedding,  drunkenness,  infidelity,  marriage,  friendship
Characters:lust
Story:talking dirty during sex,  copulation,  engagement,  coitus,  no panties,  premarital sex,  scantily clad female,  cleavage,  bare butt,  sex in bed,  leg spreading

As Good As It Gets (1997)
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. This is why As Good As It Gets (1997) is one of the best movies like Sideways (2004). (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

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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. (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

Another Year (2010) is one of the best movies like Sideways (2004)
Comedy, Drama

Another Year (2010)

A married couple who have managed to remain blissfully happy into their autumn years, are surrounded over the course of the four seasons of one average year by friends, colleagues, and family who all seem to suffer some degree of unhappiness.

Themes:unfaithfulness,  depression,  divorce,  wedding,  drunkenness,  infidelity,  friendship
Locations:restaurant
Story:golf course,  melancholy,  divorcee,  golf,  wine,  marijuana,  extramarital affair,  telephone call,  mother son relationship

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On The Road (2012)
Adventure, Drama, Romance

On The Road (2012)

Shaken by the death of his father and discouraged by his stalled career, writer Sal Paradise goes on a road trip hoping for inspiration. While traveling, he is befriended by charismatic and fearless Dean Moriarty and Moriarty's free-spirited and seductive young wife, Marylou. Traveling across the American southwest together, they strive to break from conformity and and search the unknown, and their decisions change the very course of their lives. (Read More)

Themes:friendship
Locations:motel
Characters:writer
Story:based on novel,  man crying,  on the road,  road movie,  diner,  california,  road trip,  gay slur,  marijuana,  mother son relationship,  sex scene

Alpha Dog (2006)
Biography, Crime, Drama

Alpha Dog (2006)

1999, Claremont, California. Middle-class kids, in their 20s, talk trash, wave guns, hang out in a pack. Johnny Truelove, drug dealer and son of a underworld figure, threatens Jake Mazursky, an explosive head case who owes Johnny money; Jake responds by breaking into Johnny's house. On impulse, Johnny and a couple pals kidnap Jake's 15-year-old brother, Zach. Zach's okay with it, figuring his brother will pay the debt soon. Johnny assigns his buddy Frankie to be Zach's minder, and they develop a brotherly friendship. Zach parties with his captors as things begin to spin out of control. Group think, amorality, and fear of prison assert a hold on the pack. Is Zach in danger? This is why Alpha Dog (2006) is one of the best movies like Sideways (2004). (Read More)

Themes:drunkenness,  friendship
Locations:motel,  restaurant
Characters:lust
Story:convenience store,  buddy,  breaking and entering,  answering machine,  scantily clad female,  california,  gay slur,  marijuana,  birthday,  leg spreading,  mother son relationship,  independent film,  sex scene

Mr. Woodcock (2007)
Comedy, Romance, Sport

Mr. Woodcock (2007)

Fatherless John Farley's youth frustration, even trauma, like many his school kids' in his Nebraska small town home, was the constant abuse and humiliation in sadistic Jasper Woodcock's gym class. After college, doting son John became a motivational bestseller author and returns during a book signing tour to receive the backwater's highest honor. To John's horror, his devoted mother Beverly announces her plans to marry the hated coach and he's to be celebrated on the same event as John. Only ridiculous fatso Nedderman and his strange brother try to help Farley stop Woodcock, but that keeps backfiring. (Read More)

Themes:divorce
Locations:restaurant
Characters:teacher
Story:junior high school,  engagement,  breaking and entering,  premarital sex,  author,  single mother,  gay slur,  small town,  mother son relationship,  sex scene

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Catch Me If You Can (2002) is one of the best movies like Sideways (2004)
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)
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

Five Easy Pieces (1970)
Drama

Five Easy Pieces (1970)

Robert Dupea has given up his promising career as a concert pianist and is now working in oil fields. He lives together with Rayette, who's a waitress in a diner. When Robert hears from his sister that his father isn't well, he drives up to Washington to see him, taking Rayette with him. There he gets confronted with his rich, cultured family that he had left behind. (Read More)

Themes:infidelity,  friendship
Locations:motel,  restaurant
Characters:waitress,  lust
Story:diner,  los angeles california,  failure,  melancholy,  premarital sex,  on the road,  road movie,  scantily clad female,  california,  road trip,  cleavage,  sex in bed,  small town

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Rumor Has It... (2005)
Comedy, Drama, Romance

Rumor Has It... (2005)

Hunky NY lawyer Jeff Daly finally got engaged to fickle Sarah Huttinger, who presents him to her Pasadena family, who all soon take to him, for her sister's wedding to Scott. But Jeff's clever counting makes Sarah realize her dad Earl isn't her biological father. Once movie clues from family indicate as suspect successful author Beau Burroughs, she insists on meeting him. Only like her mother and grandmother, she has a one night-stand with Beau, which may well cost her Jeff. This is why Rumor Has It... (2005) is one of the best movies like Sideways (2004). (Read More)

Themes:wedding,  unfaithfulness,  infidelity,  marriage,  friendship
Locations:restaurant,  beach
Characters:writer
Story:los angeles california,  vineyard,  premarital sex,  author,  diner,  extramarital affair,  telephone call

Nothing To Lose (1997) is one of the best movies like Sideways (2004)
Action, Adventure, Comedy, Crime

Nothing To Lose (1997)

When a man (Robbins) believes he has discovered that his wife is having an affair with his boss, it sets off a chain reaction of events. First he wanders into a ghetto where a robber (Lawrence) tries to take his money at gunpoint, but instead sets a wild ride from California to Arizona. The two eventually become reluctant friends. Discussing robbery techniques, they decide to get back at the boss by robbing an office safe containing hundreds of thousands of dollars. Life is further complicated by another pair of robbers who chase the first two for infringing on their territory. (Read More)

Themes:friendship
Locations:restaurant
Characters:waitress
Story:los angeles california,  convenience store,  answering machine,  premarital sex,  on the road,  diner,  california,  extramarital affair,  car accident,  chase,  mother son relationship

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

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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

Bad Grandpa (2013)
Comedy

Bad Grandpa (2013)

Eighty-six-year-old Irving Zisman is on a journey across America with the most unlikely companion: his eight-year-old grandson Billy, in "Jackass Presents: Bad Grandpa". Jackass characters Irving Zisman (Johnny Knoxville) and Billy (Jackson Nicoll) will take movie audiences along for the most insane hidden camera road trip ever captured on camera. Along the way Irving will introduce the young and impressionable Billy to people, places, and situations that give new meaning to the term "childrearing". The duo will encounter male strippers, disgruntled child beauty pageant contestants (and their equally disgruntled mothers), funeral home mourners, biker bar patrons, and a whole lot of unsuspecting citizens. Real people in unreal situations, making for one really messed up comedy. (Read More)

Themes:wedding
Locations:motel,  restaurant
Story:golf course,  highway travel,  man crying,  convenience store,  crying man,  on the road,  road movie,  diner,  road trip

Wonder Boys (2000) is one of the best movies like Sideways (2004)
Comedy, Drama

Wonder Boys (2000)

Grady Tripp is a professor/writer living in Pittsburgh who is struggling with writer's block. Whilst doing this, he also manages to get the chancellor pregnant. In the meantime, he and a college student, James Leer are trying to find a rare jacket once owned by Marilyn Monroe, and a college girl, Hannah Green boarding with Grady has a bit of a crush on him. This is why Wonder Boys (2000) is one of the best movies like Sideways (2004). (Read More)

Themes:writing,  divorce,  drunkenness,  marriage,  friendship
Characters:writer
Story:based on novel,  midlife crisis,  convenience store,  breaking and entering,  marijuana,  extramarital affair,  car accident

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Young Adult (2011)
Comedy, Drama

Young Adult (2011)

Thirty-seven year old Mavis Gary seems incapable of happiness. She has had one failed marriage with no romance in her immediate horizon. She ghosts writes a young adult series of books, which has just been canceled due to low sales. She is in the process of writing the last book, with which she is having a mental block. She lives vicariously through Kendall Strickland, the teenaged female heroine in her books, as like Kendall she believes her high school years were the best years of her life when she was the prom queen. When she receives news that her high school beau, Buddy Slade, and his wife, Beth Slade, have just had their first child, Mavis takes it as a sign that she and Buddy are meant to be together. As such, she devises a false pretense to travel from her Minneapolis home back her her old hometown of Mercury, Minnesota to reclaim Buddy from Beth. As Mavis slyly or not so slyly does whatever she can to hang out with Buddy, even in Beth's company if need be, she also runs into another old high school colleague named Matt Freehauf. She barely remembers Matt until she is reminded that he was the "hate crime" kid i.e. he was beaten almost to death by the school jocks who believed he was gay (which he is not), which has left him among other things needing to walk with a brace. Matt ends up being Mavis' drinking buddy and confidante, Matt, in turn, who tries to be Mavis' voice of reason to get her out of her delusional state about Buddy and get a grip on reclaiming her life as a functioning adult. (Read More)

Themes:writing,  depression,  divorce,  drunkenness,  marriage,  friendship
Locations:motel,  restaurant
Characters:writer
Story:buddy,  divorcee,  on the road,  diner,  single mother,  wine,  gay slur,  guitar,  small town,  car accident,  telephone call,  mother son relationship,  sex scene

Mike And Dave Need Wedding Dates (2016)
Adventure, Comedy, Romance

Mike And Dave Need Wedding Dates (2016)

Hard-partying brothers Mike (Adam Devine) and Dave (Zac Efron) place an online ad to find the perfect dates (Anna Kendrick, Aubrey Plaza) for their sister's Hawaiian wedding. Hoping for a wild getaway, the boys instead find themselves outsmarted and out-partied by the uncontrollable duo.

Themes:wedding,  drunkenness,  marriage,  friendship
Locations:beach
Characters:waitress
Story:wedding ceremony,  crying man,  caught having sex,  sexual attraction,  no panties,  scantily clad female,  cleavage,  bare butt,  car accident,  leg spreading,  mother son relationship,  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. (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

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Secretary (2002) is one of the best movies like Sideways (2004)
Comedy, Drama, Romance

Secretary (2002)

An emotionally fragile woman recently released from a mental hospital for self mutilation goes to school to gain secretarial skills to gain employment. She has an alcoholic father and a co-dependent mother who are clueless as to who she really is which a tormented soul who really wants to find something with which she can find success. She is a great secretary and finds a job with a unique, old fashioned, but off center in charge boss with a somewhat sadistic sexual proclivity. She grows and evolves and so does he. (Read More)

Themes:writing,  wedding,  drunkenness
Locations:restaurant,  hospital
Story:los angeles california,  crawling,  coitus,  sexual attraction,  no panties,  scantily clad female,  diner,  wine,  cleavage,  telephone call,  mother son relationship,  independent film,  one word title,  sex scene

Sunshine Cleaning (2008)
Comedy, Drama

Sunshine Cleaning (2008)

A family. Rose and Norah, in Albuquerque, lost their mother when they were young. Rose is responsible - a housecleaner, raising her seven-year-old son Oscar. She's also having an affair with Mac, a married cop, her high-school sweetheart. Norah can't hold a job. Their dad, Joe, is quirky. When Oscar is expelled for odd behavior, Rose wants to earn enough to send him to private school. Mac suggests she clean up after crime scenes, suicides, and deaths that go undiscovered for awhile. Rose enlists Norah, and Sunshine Cleaners is born. Norah bonds with the dead, Rose finds out that it's a regulated business, and complications arise. Can a family marked by tragedy sort things out? This is why Sunshine Cleaning (2008) is one of the best movies like Sideways (2004). (Read More)

Themes:unfaithfulness,  infidelity
Locations:motel,  restaurant
Characters:waitress,  teacher
Story:fast food restaurant,  medication,  diner,  single mother,  marijuana,  birthday,  extramarital affair,  bare butt,  car accident,  telephone call,  mother son relationship,  independent film

Wild Hogs (2007)
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

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Nine 1/2 Weeks (1986)
Drama, Romance

Nine 1/2 Weeks (1986)

An erotic story about a woman, the assistant of an art gallery, who gets involved in an impersonal affair with a man. She barely knows about his life, only about the sex games they play, so the relationship begins to get complicated.

Themes:divorce,  friendship
Locations:restaurant
Characters:lust
Story:crawling,  based on novel,  copulation,  divorcee,  coitus,  sexual attraction,  no panties,  scantily clad female,  wine,  gay slur,  cleavage,  sex in bed,  telephone call,  leg spreading,  chase,  sex scene

The Machinist (2004) is one of the best movies like Sideways (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

Kalifornia (1993)
Crime, Drama, Thriller

Kalifornia (1993)

Brian Kessler, a journalist researching serial killers, and his photographer girlfriend Carrie set out on a cross-country tour of the sites of the killings. Sharing the ride and their expenses are Early Grayce, a paroled white trash criminal, and his girlfriend Adele. As the trip progresses, Early begins to appear more and more unstable, and Brian and Carrie begin to fear that they may have a real-life killer in the back seat of their car. (Read More)

Themes:writing,  theft
Locations:motel
Characters:waitress,  writer
Story:on the road,  road movie,  california,  road trip,  gay slur,  bare butt,  car accident,  independent film,  one word title

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