20 movies like Sideways, ordered by similarity : The Disaster Artist(2017), The Land of Steady Habits(2018), Red Dog: True Blue(2016), Full Grown Men(2006), Congorama(2006), Pork Pie(2017), Beats(2019), American Graffiti(1973), Suddenly(2002), American Splendor(2003), Then Came You(2018), Go(1999) ...
7.5/10
Comedy, Drama
USA|Hungary
2004
126 Minutes
Paul Giamatti Thomas Haden Church Virginia Madsen Sandra Oh Marylouise Burke Jessica Hecht Missy Doty M.C. Gainey Patrick Gallagher Alex Kalognomos Joe Marinelli
writer actor waitress server wife amusing endearing playful emotional san diego wine country friendship midlife crisis male bonding affair road trip adventure temptation growing up 2000s
Two men reaching middle age with not much to show but disappointment embark on a week-long road trip through California's wine country, just as one is about to take a trip down the aisle.
7.4/10
Comedy, Drama
USA
2017
103 Minutes
James Franco Dave Franco Seth Rogen Zac Efron Alison Brie Paul Scheer Hannibal Buress Jerrod Carmichael Zoey Deutch Nathan Fielder Ari Graynor
director actor audience acting teacher friend filmmaker amusing hilarious emotional endearing passionate offbeat hollywood, calif. film set theater field restaurant apartment following your dreams filmmaker
When Greg Sestero, an aspiring film actor, meets the weird and mysterious Tommy Wiseau in an acting class, they form a unique friendship and travel to Hollywood to make their dreams come true.
6.2/10
Drama, Comedy
USA
2018
98 Minutes
Ben Mendelsohn Edie Falco Thomas Mann Charlie Tahan Connie Britton Bill Camp Elizabeth Marvel Natalie Gold Josh Pais
retiree wife drug addict teenager father son amusing hilarious emotional raw quirky moving restaurant house kitchen woods hospital bar lifestyle changes adventure
After leaving his wife and his job to find happiness, Anders befriends a drug-addicted teen, sending him down a path of reckless and shameful behavior.
6.4/10
Comedy, Drama
Australia
2016
88 Minutes
Jason Isaacs Thomas Cocquerel Levi Miller Bryan Brown Hanna Mangan Lawrence John Jarratt Justine Clarke Steve Le Marquand
father son brother dog pet pet owner animal endearing emotional heartwarming playful positive australia pet care human connection human-animal friendship family childhood trials life
An iconic Australian story of family, friendship and adventure, between a young boy and a scrappy one-of-a-kind dog that would grow up to become an Australian legend.
4.9/10
Comedy, Drama
USA
2006
78 Minutes
Matt McGrath Judah Friedlander Alan Cumming Amy Sedaris Jim Fyfe Jerry Grayson Deborah Harry Katie Kreisler Joie Lee
father husband young boy mother childhood friend bartender endearing playful spirited house car amusement park bar trailer florida road trip self-discovery friendship family responsibility
A man stuck in the reveries of his youth tracks down the boyhood friend he once tormented, only to find that simpler times were more complicated than he thought.
7.1/10
Comedy, Drama
Canada|Belgium|France
2006
105 Minutes
Olivier Gourmet Paul Ahmarani Jean-Pierre Cassel Gabriel Arcand Lorraine Pintal Guy Pion Janine Sutto Marie Brassard Henri Chassé
engineer inventor writer son father wife offbeat intricate endearing belgium quebec canada road family secrets family bloodline journey inventions adoption friendship adventure
An eccentric Belgian inventor travels to Québec to search for his family, which uncovers a secret history between two seemingly unrelated people.
Crime, Comedy, Drama, Action
2017
105 Minutes
Dean O'Gorman James Rolleston Ashleigh Cummings Antonia Prebble Matt Whelan Ben Mitchell Milo Cawthorne Siobhan Marshall
outlaw cop friend boyfriend girlfriend driver amusing engaging endearing thrilling heartwarming new zealand vehicle barn road on the run big city on the run road trip protest
Accidental outlaws travel New Zealand in a yellow mini, protesting conformity and chasing lost love, with the cops and the media hot on their tail.
7.1/10
Comedy, Drama
UK
2019
101 Minutes
Martin Donaghy Brian Ferguson Ryan Fletcher Laura Fraser Rachel Jackson Neil Leiper Lorn Macdonald Kevin Mains
scottish person teenager best friend parent partygoer amusing emotional engaging frenetic gutsy unrestrained scotland home city party rave street friendship rave culture drugs
Two teenage boys in Scotland in 1994, best friends with no control over their lives, risk everything to attend an illegal rave, hoping for the best night of their boring lives.
7.4/10
Comedy, Drama
USA
1973
110 Minutes
Richard Dreyfuss Ron Howard Paul Le Mat Charles Martin Smith Cindy Williams Candy Clark Mackenzie Phillips Wolfman Jack Harrison Ford Bo Hopkins Manuel Padilla Jr.
good guy loser dreamer girlfriend dj amusing cool endearing california restaurant car radio station street cars music romance male bonding friendship growing up love
A couple of high school grads spend one final night cruising the strip with their buddies before they go off to college.
Comedy, Drama
2002
94 Minutes
Tatiana Saphir Carla Crespo Veronica Hassan Beatriz Thibaudin María Merlino Marcos Ferrante Ana María Martínez Susana Pampin Luis Herrera
lonely woman teen girl rebel lesbian kidnapper playful offbeat touching buenos aires, argentina shop cab beach road kidnapping road trip self-discovery female bonding boredom adventure discovery
Two lesbians (Carla Crespo, Veronica Hassan) force a lonely, overweight saleswoman (Tatiana Saphir) into a cab and take her on a road trip.
7.4/10
Comedy, Biography, Drama
USA
2003
100 Minutes
Paul Giamatti Robert Pulcini Earl Billings James Urbaniak Judah Friedlander Robert Pulcini Toby Radloff Hope Davis Joyce Brabner Donal Logue Molly Shannon
writer wife friend engaging playful quirky cleveland ohio household writers romance blue collar comic books underdog love 2000s
An original mix of fiction and reality illuminates the life of comic book hero everyman Harvey Pekar.
7.0/10
Romance, Comedy, Drama
USA
2018
99 Minutes
Asa Butterfield Maisie Williams Nina Dobrev Tyler Hoechlin Peyton List Ken Jeong David Koechner Tituss Burgess Sonya Walger Ann Osmond Colin Moss
hypochondriac terminally ill person friend family amusing charming cheeky creative emotional fiery hilarious inspiring playful quirky sad spirited wild united states terminal illness hypochondria
A hypochondriac working as an airport baggage handler is forced to confront his fears when a British teenager with a terminal illness enlists him to help her carry out her eccentric bucket list.
Comedy, Drama
1999
103 Minutes
Desmond Askew Taye Diggs William Fichtner J.E. Freeman Katie Holmes Jane Krakowski Breckin Meyer Jay Mohr Timothy Olyphant Sarah Polley Scott Wolf
storekeeper drug dealer undercover cop teen girl wife actor frenetic playful cool grocery store street car los angeles las vegas strip club drugs set-up accident hedonism road trip
A checkout girl covering for a co-worker (Desmond Askew) faces danger from a drug dealer she double-crosses out of desperation.
6.4/10
Comedy, Drama
Canada
2016
101 Minutes
Clive Owen Jaeden Martell Maria Bello Robert Forster Tim Blake Nelson Patton Oswalt Matthew Modine Stephen Tobolowsky
carpenter thief son father family mother charming endearing heartwarming lighthearted moving playful canada small town home father/son relationship fatherhood bonding life lessons growing up
A divorced father and his eight-year-old son are about to spend a somewhat predictable weekend together, nevertheless, when a valuable toolbox gets stolen, the search for the thieves will soon turn into a true family bonding.
4.8/10
Comedy, Drama
USA
2018
78 Minutes
Mia Rose Frampton Stony Blyden Beau Brooks Lauren Giraldo Pej Vahdat Beth Lacke Juliette Angelo Kate Rachesky
cancer patient survivor boyfriend friend family member amusing endearing moving touching charming high school cafeteria hospital doctor's office gym classroom survival new life second chance friendship
When 18 year old Hope Gracin suddenly finds herself in remission from end-stage cancer, she must learn to live without an expiration date.
Comedy, Drama
2003
89 Minutes
Kate Dollenmayer Christian Rudder Myles Paige Jennifer L. Schaper Lissa Patton Rudder Marshall Lewy Andrew Bujalski
college graduate coworker friend love interest tattoo artist amusing brooding emotional intricate boston office household relationships friendship love alcohol maturing responsibility growing up love
4.8/10
Comedy, Drama
USA
2019
98 Minutes
Ellar Coltrane Ian Nelson Analeigh Tipton Callan McAuliffe Ella Hunt Bill Milner Hayden Szeto Lana Condor Victoria Justice
best friend band member friend love interest girlfriend cheeky amusing emotional charming stage bar woods house apartment growing up friendship romance broken heart love triangle love
A coming-of-age story about the complexities of young romantic relationships.
6.3/10
Comedy, Drama
USA
2016
92 Minutes
Katee Sackhoff Jade Pettyjohn Heather Matarazzo Jeremy Sisto Judy Reyes Diego Josef Isaiah Mustafa Jonah Beres
young girl mother sister classmate friend young boy cheeky amusing emotional california school house classroom bathroom bedroom menstruation growing up immaturity friendship self-esteem
Bird, 12, has to become a woman whether she wants to or not when - in the worst week of her life - she gets her first period, is ditched by her impulsive, free spirited mom, and learns that you can never really go back to The Valley.
6.0/10
Comedy, Drama
USA
2017
90 Minutes
Zoey Deutch Kathryn Hahn Tim Heidecker Adam Scott Joey Morgan Dylan Gelula Maya Eshet Eric Edelstein Romy Byrne
teenager mother stepfather stepbrother vigilante friend amusing brash unrestrained suspenseful emotional gutsy los angeles san fernando valley car pool restaurant bowling alley revenge growing up
A sexually curious teen forms an unorthodox kinship with her mentally unstable stepbrother.
6.3/10
Comedy, Drama
USA
2014
94 Minutes
Ben Stiller Naomi Watts Adam Driver Amanda Seyfried Charles Grodin Adam Horovitz Maria Dizzia Ryan Serhant Dree Hemingway Matthew Maher Brady Corbet
filmmaker wife middle-aged man middle-aged woman couple friend amusing charming cheery classroom club apartment subway new york city street middle age age difference acceptance youth friendship
A middle-aged couple's career and marriage are overturned when a disarming young couple enters their lives.
7.1/10
Romance, Comedy, Drama
Spain|USA
2008
96 Minutes
Javier Bardem Patricia Clarkson Penélope Cruz Kevin Dunn Rebecca Hall Scarlett Johansson Chris Messina Carrie Preston Pablo Schreiber Zak Orth Abel Folk
ladies' man american painter tourist ex-wife amusing playful emotional barcelona, spain apartment love triangle party art forbidden love temptation 2000s
Two friends on a summer holiday in Spain become enamored with the same painter, unaware that his ex-wife, with whom he has a tempestuous relationship, is about to re-enter the picture.
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