Movies like Sideways

If you like "Sideways" you are looking for talky, humorous and semi serious movies about / with road trip, wine, friendship, golf, writers, midlife crisis and vacation themes of Comedy, Drama and Romance genre shot in USA or Hungary.
Find your next favorite and similar movies in two steps: 1. Identify all themes of interest from this film (block below). 2. Look for them in the presented list.
Sideways (2004)
 7.5
 182K
Sideways (2004)
Genre: Comedy, Drama, Romance
Country: USA, Hungary
Duration: 127 min.
Story: Two middle-aged men embark on a spiritual journey through Californian wine country. One is an unpublished novelist suffering from depression, and the other is only days away from walking down the aisle.
Style: talky, humorous, semi serious, sentimental, road movie, melancholic, witty, realistic, emotional, clever ...
Plot: road trip, wine, friendship, golf, writers, midlife crisis, vacation, on the road, depression, fall in love, best friends, love and romance, couples, lifestyle, nothing goes right, actor, deception, divorced divorcee, marijuana, buddy, winery, wine tasting, unlikely friendships, character study, life philosophy ...
Time: contemporary, 21st century
Place: california, usa, los angeles, san diego california

Movie in categories

road trip movies
1237
wine movies
1667
california movies
3297
friendship movies
14275
golf movies
577
writers movies
4888
vacation movies
847

Most similar movies to Sideways

The list contains related movies ordered by similarity. Recommendation engine sorted out realistic, semi serious, melancholic and talky films with plots about unlikely friendships, dialogue, mentor, storytelling, friendship, relationships and honest mostly in Comedy, Drama and Romance genres. Some movies like Sideways: Friends with Money (2006), Smart People (2008), Celeste & Jesse Forever (2012), The Trip (2010), Husbands and Wives (1992). The matching attributes are highlighted in bold.
Friends with Money (2006)
Genre: Comedy, Drama, Romance
Country: USA
Duration: 88 min.
Story: After she quits her lucrative job, Olivia finds herself unsure about her future and her relationships with her successful and wealthy friends.
Style: witty, semi serious, humorous, sentimental, melancholic ...
Audience: girls' night
Plot: friendship, midlife crisis, marriage, maid, love and romance, crumbling marriage, money, power relations, looking for love, master and servant, unfulfillment, couples ...
Time: contemporary, 2000s
Place: los angeles, california, usa, santa monica california, new jersey
⇓ similarity ⇓
100%
 6.1
 22K
Smart People (2008)
Genre: Comedy, Drama, Romance
Country: USA
Duration: 95 min.
Story: Professor Lawrence Wetherhold (Dennis Quaid) might be imperiously brilliant, monumentally self-possessed and an intellectual giant -- but when it comes to solving the conundrums of love and family, he's as downright flummoxed as the next guy.
Style: humorous, realistic, contemplative, touching, sentimental ...
Plot: self discovery, family relations, parents and children, couple relations, introspection, family life, couples, romance, hopes, love and romance, siblings relations, alienation ...
Time: 21st century, contemporary
Place: usa, pittsburgh, new york, pennsylvania, new jersey
⇓ similarity ⇓
40%
Celeste & Jesse Forever (2012)
Genre: Comedy, Drama, Romance
Country: USA
Duration: 92 min.
Story: Celeste and Jesse met in high school and got married young. They laugh at the same jokes and finish each other’s sentences. They are forever linked in their friends’ minds as the perfect couple – she, a high-powered businesswoman and budding ...
Style: humorous, semi serious, sentimental, melancholic, romantic ...
Audience: date night, chick flick, girls' night
Plot: friendship, divorce, best friends, romance, couples, love and romance, lifestyle, starting over, looking for love, hopes, breakup, thirtysomething life ...
Time: 21st century, contemporary
Place: los angeles, usa, new jersey, california, san francisco
⇓ similarity ⇓
37%
 7.0
 22K
The Trip (2010)
Genre: Comedy, Drama
Country: UK
Duration: 112 min.
Story: When Steve Coogan is asked by The Observer to tour the country's finest restaurants, he envisions it as the perfect getaway with his beautiful girlfriend. But, when she backs out on him, he has no one to accompany him but his best friend and ...
Style: humorous, semi serious, melancholic, atmospheric, surreal ...
Plot: on the road, restaurant, friendship, lifestyle, artists and showbiz, countryside, loneliness, midlife crisis, eccentricity, existentialism, sarcasm, beautiful scenery ...
Time: contemporary, 21st century
Place: england, northern england, london
⇓ similarity ⇓
34%
Movie in collections
Husbands and Wives (1992)
Genre: Comedy, Drama, Romance
Country: USA
Duration: 108 min.
Story: When Jack and Sally announce that they're splitting up, this comes as a shock to their best friends Gabe and Judy. Maybe mostly because they also are drifting apart and are now being made aware of it. So while Jack and Sally try to go on and ...
Style: talky, realistic, sincere, semi serious, melancholic ...
Plot: infidelity, marriage, breakup, friendship, dishonesty, family problems, teacher student relationship, friends, romance, couple relations, fall in love, human nature ...
Time: 20th century, 90s, 70s
Place: new york, usa, manhattan new york city
⇓ similarity ⇓
32%
Dinner with Friends (2001)
Genre: Comedy, Drama, Romance
Country: USA
Duration: 94 min.
Story: A husband and wife reevaluate their marriage after their closest friends, another couple decide to split up after twelve years.
Style: talky, sincere, realistic, witty, stylized ...
Audience: girls' night
Plot: friendship, family problems, introspection, relationships, infidelity, crumbling marriage, love and romance, midlife crisis, dinner, starting over, honest, betrayal ...
Time: 21st century, contemporary, 80s
Place: new york, usa, connecticut, new jersey, california ...
⇓ similarity ⇓
31%
 7.1
 124K
About Schmidt (2002)
Genre: Comedy, Drama
Country: USA
Duration: 125 min.
Story: 66-year-old Warren Schmidt is a retired insurance salesman and has no particular plans other than to drive around in the motor home his wife insisted they buy. He's not altogether bitter, but not happy either, as everything his wife does annoys ...
Style: contemplative, tragicomedy, humorous, semi serious, road movie ...
Plot: life changing, family life, on the road, wedding, letter, salesman, fish out of water, parents and children, golden years, introspection, elderly, understanding ...
Time: 21st century, contemporary
Place: kansas, colorado, denver colorado, nebraska, california
⇓ similarity ⇓
31%
Friends with Kids (2011)
Genre: Comedy, Drama, Romance
Country: USA
Duration: 107 min.
Story: In the wake of their friends' marriages and eventual offspring, longtime pals Julie and Jason decide to have a child together without becoming a couple. By becoming "time-share" parents, they reason, they can experience the joys of ...
Style: touching, realistic, humorous, sentimental, semi serious ...
Audience: date night, kids, chick flick, teens, girls' night
Plot: friendship, best friends in love, relationship problems, platonic, best friend, romance, couple relations, best friends, love and romance, lifestyle, thirtysomething life, friends ...
Time: contemporary, 21st century
Place: new york, usa, brooklyn new york city, vermont, california ...
⇓ similarity ⇓
31%
Movie in collections
The Puffy Chair (2005)
Genre: Comedy, Drama, Romance
Country: USA
Duration: 85 min.
Story: Josh's life is pretty much in the toilet. He's a failed NYC indie rocker, and a failing booking agent. But he finds the potential of a small victory in a really bad idea. He decides to purchase a 1985 Lazy Boy on eBay, just like the one ...
Style: road movie, mumblecore, humorous, melancholic, stylized ...
Audience: date night
Plot: road trip, on the road, family relations, wedding, parents and children, introspection, hopes, self discovery, love and romance, brother brother relationship, couple relations, gift ...
Time: contemporary, 21st century
Place: new york, usa, atlanta georgia
⇓ similarity ⇓
29%
 7.4
 322K
Up in the Air (2009)
Genre: Comedy, Drama, Romance
Country: USA
Duration: 109 min.
Story: George Clooney plays the dry cynical character of Ryan Bingham, an executive who specializes in "downsizing". Ryan lives out of his suitcase, traveling the country for the sole purpose terminating unwanted employees day after day. Just as ...
Style: touching, thought provoking, cynical, humorous, sexy ...
Audience: date night
Plot: on the road, loneliness, love affair, business trip, love and romance, couples, business, relationship vs career, introspection, unfulfillment, top executive, power relations ...
Time: 21st century, contemporary
Place: las vegas, usa, kansas city, miami, detroit ...
⇓ similarity ⇓
28%
 4.9
 185
Sam the Man (2001)
Genre: Comedy, Drama, Romance
Country: USA
Duration: 87 min.
Story: Before he broke out with the J.D. Salinger-esque Tadpole in 2002, producer-turned-director Gary Winick filmed this little-seen relationship drama. Fisher Stevens stars as the title character, a writer with one novel under his belt who can't ...
Style: semi serious, realistic, suspense, sincere, sentimental ...
Audience: date night
Plot: infidelity, looking for love, love and romance, couples, estrangement, breakup, lifestyle, romance, womanizer, dishonesty, bittersweet, artists and showbiz ...
Time: contemporary, 21st century
Place: new york, usa
⇓ similarity ⇓
28%
Waking Up in Reno (2002)
Genre: Comedy, Romance
Country: USA
Duration: 91 min.
Story: Candy and Lonnie Earl are just crazy about each other. The problem: she's married to Roy and he's married to Darlene. So far it's been a secret affair. But that's about to change, because this foursome is driving cross-country ...
Style: humorous, semi serious, witty, funny, talky ...
Audience: date night
Plot: infidelity, romance, unfulfillment, love and romance, partners, crumbling marriage, nothing goes right, dishonesty, buddies, on the road, couple relations, road trip ...
Time: contemporary
Place: usa, arkansas, nevada
⇓ similarity ⇓
26%
The Anniversary Party (2001)
Genre: Comedy, Drama, Romance
Country: USA
Duration: 115 min.
Story: While celebrating their reconciliation and six years of marriage, the American actress Sally Nash (Jennifer Jason Leigh) and the British novelist Joe Therrian (Alan Cumming) receive their close friends, some colleagues and their next door neighbors ...
Style: cynical, humorous, melancholic, satirical, talky ...
Plot: infidelity, party, love and romance, lifestyle, family problems, couple relations, couples, crumbling marriage, dishonesty, anniversary, marital crisis, dysfunctional relationship ...
Time: contemporary
Place: california, usa, los angeles
⇓ similarity ⇓
26%
Melvin Goes to Dinner (2003)
Genre: Comedy, Drama, Romance
Country: USA
Duration: 83 min.
Story: Marital infidelity, religion, a guy in heaven wearing a Wizards jersey, anal fetishes, cigarettes and schizophrenia, ghosts, and how it's going to get worse before it gets better.
Style: humorous, intellectual, witty, melancholic, talky ...
Plot: friendship, infidelity, fetish, self discovery, introspection, buddies, couple relations, ghost, adultery, schizophrenic, husband wife relationship, stewardess ...
Time: contemporary
Place: new jersey
⇓ similarity ⇓
26%
Friends & Lovers (1999)
Genre: Drama, Romance, Comedy
Country: USA
Duration: 103 min.
Story: Friends for ten years, a group of twenty-somethings head for the ski slopes as guests of Ian's father. (Ian and dad are estranged because dad worked too many hours when Ian was a lad.) Dad has something to say, but Ian won't listen. ...
Style: sexy, humorous, realistic, melancholic, clever ...
Audience: girls' night, date night, teens
Plot: friendship, thirtysomething life, midlife crisis, infidelity, romance, lifestyle, sex, pregnancy, skiing, existentialism, relationships, honest ...
Time: 90s
Place: new jersey
⇓ similarity ⇓
50%
 6.1
 36K
Greenberg (2010)
Genre: Comedy, Drama, Romance
Country: USA
Duration: 107 min.
Story: A New Yorker moves to Los Angeles in order to figure out his life while he housesits for his brother, and he soon sparks with his brother's assistant.
Style: semi serious, psychological, sincere, satirical, twists and turns ...
Plot: old love, friendship, personal assistant, starting over, misfit, self fulfillment, fall in love, reunion, mentally unstable, love and romance, buddies, escape from reality ...
Time: contemporary, 21st century
Place: los angeles, california, usa, new york, brooklyn new york city ...
⇓ similarity ⇓
25%
Sex and the City (2008)
Genre: Comedy, Drama, Romance
Country: USA
Duration: 145 min.
Story: A New York writer on sex and love is finally getting married to her Mr. Big. But her three best girlfriends must console her after one of them inadvertently leads Mr. Big to jilt her.
Style: witty, light, romantic, emotional, erotic ...
Audience: chick flick, girls' night, date night, teens
Plot: fashion, friends, love and romance, city life, friendship, lifestyle, couple relations, sexual relations, family relations, urban, best friends, female friendship ...
Time: contemporary, 21st century, 2000s
Place: new york, usa, manhattan, new york city, manhattan new york city, malibu california ...
⇓ similarity ⇓
25%
 7.0
 14K
Chinese Puzzle (2013)
Genre: Comedy, Drama, Romance
Country: France, USA, Belgium
Duration: 117 min.
Story: Xavier is a 40-year-old father of two who still finds life very complicated. When the mother of his children moves to New York, he can't bear them growing up far away from him and so he decides to move there as well.
Style: humorous, touching, realistic, feel good, witty ...
Audience: date night
Plot: friendship, midlife crisis, immigrants, fake marriage, starting over, longing, old love, fall in love, parents and children, family problems, couples, love and romance ...
Time: contemporary, 21st century, 2010s
Place: new york, usa, paris france, france, new jersey
⇓ similarity ⇓
24%
Movie in collections
 6.4
 41K
The Last Kiss (2006)
Genre: Comedy, Drama, Romance
Country: USA, Canada
Duration: 115 min.
Story: Revolves around a young couple and their friends struggling with adulthood and issues of relationships and commitment. Based on the 2001 Italian film L'ultimo bacio, directed by Gabriele Muccino.
Style: sentimental, touching, humorous, emotional, intense ...
Audience: date night, chick flick, girls' night
Plot: battle of the sexes, pregnancy, casual sex, romance, wedding, infidelity, introspection, human nature, power of love, free spirited, youth, couples ...
Time: contemporary, 21st century
Place: usa, cape town south africa, sydney australia, florence italy, patagonia ...
⇓ similarity ⇓
24%
Drinking Buddies (2013)
Genre: Comedy, Drama, Romance
Country: USA
Duration: 90 min.
Story: Weekend trips, office parties, late night conversations, drinking on the job, marriage pressure, biological clocks, holding eye contact a second too long… you know what makes the line between “friends” and “more than friends” really ...
Style: semi serious, humorous, mumblecore, melancholic, enigmatic ...
Plot: love triangle, profanity, relationships, romance, couple relations, couples, lifestyle, love and romance, weekend, unfulfillment, boyfriend girlfriend relationship, group of friends ...
Time: 21st century, contemporary, 70s
Place: usa, chicago illinois, illinois, new jersey
⇓ similarity ⇓
23%
California Suite (1978)
Genre: Comedy, Drama, Romance
Country: USA
Duration: 103 min.
Story: Misadventures of four groups of guests at the Beverly Hills Hotel.
Style: talky, witty, clever, humorous, captivating ...
Plot: hotel, multiple storylines, womanizer, tennis, custody, friendship, romance, gays and lesbians, dishonesty, lifestyle, love and romance, love affair ...
Time: 70s, 20th century, 1930s
Place: california, usa, beverly hills, los angeles, new york ...
⇓ similarity ⇓
23%
 7.9
 133K
Manhattan (1979)
Genre: Comedy, Drama, Romance
Country: USA
Duration: 96 min.
Story: The life of a divorced television writer dating a teenage girl is further complicated when he falls in love with his best friend's mistress.
Style: intellectual, humorous, sincere, realistic, semi serious ...
Audience: date night
Plot: adultery, mistress, love triangle, age difference, divorce, crumbling relationship, city life, dating, romance, friendship, love affair, looking for love ...
Time: 20th century, 70s
Place: new york, manhattan new york city, usa, manhattan, new york city
⇓ similarity ⇓
23%
 7.0
 60K
Enough Said (2013)
Genre: Comedy, Drama, Romance
Country: USA
Duration: 93 min.
Story: Eva is a divorced soon-to-be empty-nester wondering about her next act. Then she meets Marianne, the embodiment of her perfect self. Armed with a restored outlook on being middle-aged and single, Eva decides to take a chance on her new love interest ...
Style: touching, sincere, sentimental, melancholic, romantic ...
Audience: chick flick
Plot: dating, party, divorced divorcee, poet, romance, goodhearted, couple relations, middle aged, single parent, sexual activity, encounter, masseuse ...
Time: contemporary, 21st century
Place: usa, california, united states, new jersey, los angeles
⇓ similarity ⇓
23%
Movie in collections
 7.4
 12K
Ten Inch Hero (2007)
Genre: Comedy, Drama, Romance
Country: USA
Duration: 102 min.
Story: Four friends search for love and happiness while working at a California sandwich shop.
Style: touching, witty, feel good, sentimental, humorous ...
Audience: girls' night, date night, chick flick, teens
Plot: looking for love, friends, fall in love, friendship, love and romance, restaurant, shyness, young people, love story, lifestyle, happy ending, twentysomething life ...
Time: 21st century, contemporary
Place: usa, california
⇓ similarity ⇓
23%
Your Friends & Neighbors (1998)
Genre: Comedy, Drama, Romance
Country: USA
Duration: 100 min.
Story: This adult comedy follows six characters, three men and three women from a cross-section of social groups, as they play sexual power games. When an affair fires up between 2 of the married characters, it sparks a chain of consequences for all of ...
Style: sexual, sexy, humorous, semi serious, realistic ...
Audience: girls' night
Plot: infidelity, extramarital affair, unhappiness, male friendship, friendship between men, dark humor, betrayal, couple relations, love affair, looking for love, thirtysomething life, battle of the sexes ...
Time: 90s
⇓ similarity ⇓
23%
 6.1
 9K
Duets (2000)
Genre: Comedy, Drama, Music, Romance
Country: USA
Duration: 112 min.
Story: Duets is a road-trip comedy which revolves around the little known world of karaoke and the whimsical characters who inhabit it. All roads lead to Omaha, site of a national karaoke competition where this motley group of singers and stars come ...
Style: humorous, touching, sentimental, entertaining, clever ...
Audience: date night, chick flick
Plot: family relations, partners, love and romance, contests and competitions, ambition, singing contest, singing competition, musician, singing, karaoke, on the road, road trip ...
Time: 90s
Place: las vegas, usa, nevada, utah, new jersey ...
⇓ similarity ⇓
23%
 6.3
 23K
Shopgirl (2005)
Genre: Drama, Romance
Country: USA
Duration: 106 min.
Story: Mirabelle is a disenchanted salesgirl and aspiring artist who sells gloves and accessories at a department store. She has two men in her life: wealthy divorcée Ray Porter and struggling musician Jeremy. Mirabelle falls in love with the glamorous ...
Style: touching, sentimental, realistic, semi serious, emotional ...
Audience: date night, girls' night, chick flick
Plot: love triangle, salesman, romance, fall in love, twentysomething life, lifestyle, unfulfillment, dull life, artist, depression, unlikely friendships, honest ...
Time: 21st century, contemporary, 2000s
Place: los angeles, california, usa, beverly hills, vermont ...
⇓ similarity ⇓
23%
Barney's Version (2010)
Genre: Comedy, Drama
Country: Italy, Canada
Duration: 134 min.
Story: The picaresque and touching story of the politically incorrect, fully lived life of the impulsive, irascible and fearlessly blunt Barney Panofsky.
Style: emotional, semi serious, witty, sincere, thought provoking ...
Plot: suicide, marriage, friendship, everyday life, lifestyle, human nature, marital problem, love and romance, aging, divorce, jewish, actress ...
Time: 70s, 90s, 80s, 20th century, year 1974 ...
Place: canada, rome italy, montreal quebec, italy, montreal ...
⇓ similarity ⇓
22%
 7.1
 9K
The Wood (1999)
Genre: Comedy, Drama, Romance
Country: USA
Duration: 106 min.
Story: In the panicky, uncertain hours before his wedding, a groom with prenuptial jitters and his two best friends reminisce about growing up together in the middle-class African-American neighborhood of Inglewood, California. Flashing back to the ...
Style: feel good, humorous, realistic, touching, semi serious ...
Audience: teens, date night, girls' night
Plot: friendship, wedding, coming of age, high school, homecoming, friendship between men, family relations, adolescence vs adulthood, siblings relations, best friends, twentysomething life, love and romance ...
Time: 80s
Place: california, usa, new jersey, texas
⇓ similarity ⇓
22%
Kicking and Screaming (1995)
Genre: Comedy, Drama, Romance
Country: USA
Duration: 96 min.
Story: After college graduation, Grover's girlfriend Jane tells him she's moving to Prague to study writing. Grover declines to accompany her, deciding instead to move in with several friends, all of whom can't quite work up the inertia to ...
Style: talky, humorous, realistic, semi serious, melancholic ...
Plot: friendship, college, coming of age, graduation, lifestyle, buddies, twentysomething life, drinking alcohol, drinking, student, husband wife relationship, roommate ...
Time: 20th century, 90s, 1990s
Place: usa, new york, brooklyn new york city, prague, manhattan new york city ...
⇓ similarity ⇓
22%