Small Films (?)    
Showing best popular movies like Sideways:
Want more independent & international films similar to Sideways?
<< FIND THEM HERE! >>
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:
Mood:
Locations:
Characters:
Story: (See All)

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:
Locations:
Characters:
Story:

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:
Locations:
Characters:
Story:

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:
Locations:
Characters:
Story:

Sex And Lucía (2001) is one of the best movies like Sideways (2004)
Drama, Romance

Sex And Lucía (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:
Locations:
Characters:
Story:

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:
Locations:
Characters:
Story:

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:
Characters:
Story:

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:
Mood:
Locations:
Characters:
Story:

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:
Locations:
Characters:
Story:

Swingers (1996)
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:
Locations:
Characters:
Story:

Terms Of Endearment (1983)
Comedy, Drama

Terms Of Endearment (1983)

Aurora and Emma are mother and daughter who march to different drummers. Beginning with Emma's marriage, Aurora shows how difficult and loving she can be. The movie covers several years of their lives as each finds different reasons to go on living and find joy. Aurora's interludes with Garrett Breedlove, retired astronaut and next door neighbor are quite striking. In the end, different people show their love in very different ways. (Read More)

Themes:
Locations:
Characters:
Story:

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:
Locations:
Characters:
Story:

Adore (2013) is one of the best movies like Sideways (2004)
Drama, Romance

Adore (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. (Read More)

Themes:
Locations:
Characters:
Story:

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:
Locations:
Characters:
Story:

Y Tu Mamá También (2001)
Adventure, Comedy, Drama, Romance

Y Tu Mamá También (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:
Locations:
Characters:
Story:

Forgetting Sarah Marshall (2008)
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:
Mood:
Locations:
Characters:
Story:

The Last Kiss (2006) is one of the best movies like Sideways (2004)
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:
Characters:
Story:

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:
Locations:
Characters:
Story:

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. (Read More)

Themes:
Mood:
Locations:
Characters:
Story:

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:
Locations:
Characters:
Story:

Sliding Doors (1998) is one of the best movies like Sideways (2004)
Comedy, Drama, Fantasy, Romance

Sliding Doors (1998)

In London, the public relation Helen is fired from her position in a PR company. While returning home, she does not catch the train in the subway. But in another possibility of her life, she catches the train in the subway. The story shows two parallel lives of Helen: in one life, she stays with her boyfriend Gerry, and in the other life, she finds that Gerry cheats her with Lydia and falls in love with James Hammerton. (Read More)

Themes:
Locations:
Characters:
Story:

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:
Locations:
Characters:
Story:

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:
Mood:
Locations:
Story:

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:
Mood:
Locations:
Characters:
Story:

Rumor Has It... (2005) is one of the best movies like Sideways (2004)
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. (Read More)

Themes:
Locations:
Characters:
Story:

Up In The Air (2009)
Drama, Romance

Up In The Air (2009)

Ryan Bingham is a corporate downsizing expert whose cherished life on the road is threatened just as he is on the cusp of reaching ten million frequent flyer miles and just after he's met the frequent-traveler woman of his dreams.

Themes:
Locations:
Story:

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:
Locations:
Characters:
Story:

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:
Locations:
Characters:
Story:

Harold & Kumar Go To White Castle (2004) is one of the best movies like Sideways (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:
Locations:
Story:

The Heartbreak Kid (2007)
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:
Characters:
Story:

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:
Mood:
Locations:
Characters:
Story:

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:
Mood:
Locations:
Characters:
Story:

The Unbearable Lightness Of Being (1988) is one of the best movies like Sideways (2004)
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:
Locations:
Characters:
Story:

9½ Weeks (1986)
Drama, Romance

9½ 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:
Locations:
Characters:
Story:

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? (Read More)

Themes:
Locations:
Characters:
Story:

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.

Themes:
Locations:
Characters:
Story:

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? (Read More)

Themes:
Locations:
Characters:
Story:

Little Miss Sunshine (2006)
Comedy, Drama

Little Miss Sunshine (2006)

In Albuquerque, Sheryl Hoover brings her suicidal brother Frank to the breast of her dysfunctional and emotionally bankrupted family. Frank is homosexual, an expert in Proust. He tried to commit suicide when he was rejected by his boyfriend and his great competitor became renowned and recognized as number one in the field of Proust. Sheryl's husband Richard is unsuccessfully trying to sell his self-help and self-improvement technique using nine steps to reach success, but he is actually a complete loser. Her son Dwayne has taken a vow of silence as a follower of Nietzsche and aims to be a jet pilot. Dwayne's grandfather Edwin was sent away from the institution for elders (Sunset Manor) and is addicted in heroin. When her seven-year-old daughter Olive has a chance to dispute the Little Miss Sunshine pageant in Redondo Beach, California, the whole family travels together in their old Volkswagen Type 2 (Kombi) in a funny journey of hope of winning the talent contest and to make a dream come true. (Read More)

Themes:
Locations:
Characters:
Story:

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:
Locations:
Characters:
Story:

Waitress (2007) is one of the best movies like Sideways (2004)
Comedy, Drama, Romance

Waitress (2007)

Jenna is unhappily married, squirreling away money, and hoping to win a pie-baking contest so, with the prize money, she'll have enough cash to leave her husband Earl. She finds herself pregnant, which throws her plans awry. She bakes phenomenal pies at Joe's diner, listens to old Joe's wisdom, tolerates her sour boss Cal, is friends with Dawn and Becky (her fellow waitresses), and finds a mutual attraction with the new doctor in town. As the pregnancy advances, life with Earl seems less tolerable, a way out less clear, and the affair with the doctor complicated by his marriage. What options does a waitress have? (Read More)

Themes:
Locations:
Characters:
Story:

Lolita (1997)
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. (Read More)

Themes:
Locations:
Characters:
Story:

The Graduate (1967)
Comedy, Drama

The Graduate (1967)

Ben has recently graduated from college, with his parents now expecting great things from him. At his "Homecoming" party, Mrs. Robinson, the wife of his father's business partner, has Ben drive her home, which leads to an affair between the two. The affair eventually ends, but comes back to haunt him when he finds himself falling for Elaine, Mrs. Robinson's daughter. (Read More)

Themes:
Mood:
Locations:
Characters:
Story:

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:
Locations:
Characters:
Story:

Clerks II (2006) is one of the best movies like Sideways (2004)
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:
Locations:
Story:

Boogie Nights (1997)
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:
Locations:
Characters:
Story:

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:
Characters:
Story:

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:
Locations:
Characters:
Story:

Wild At Heart (1990) is one of the best movies like Sideways (2004)
Comedy, Crime, Drama, Thriller

Wild At Heart (1990)

Lula's psychopathic mother goes crazy at the thought of Lula being with Sailor, who just got free from jail. Ignoring Sailor's probation, they set out for California. However their mother hires a killer to hunt down Sailor. Unaware of this, the two enjoy their journey and themselves being together... until they witness a young woman dying after a car accident - a bad omen. (Read More)

Themes:
Mood:
Locations:
Characters:
Story:

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. (Read More)

Themes:
Locations:
Characters:
Story:

Showing 50 most popular matches above.
Looking for arthouse and lower-budget films similar to Sideways?
<< FIND THEM HERE! >>
(Poster artwork courtesy of TheMovieDB.org)