20 movies like Free Enterprise, ordered by similarity : In the Soup(1992), Barfly(1987), Room to Rent(2000), Barbershop: The Next Cut(2016), Factotum(2005), Star Maps(1997), Crime Wave(1985), Ghostbusters(1984), Spellbound(2002), Paterson(2016), Booksmart(2019), The Muppets(2011) ...
6.7/10
Comedy
USA
1998
116 Minutes
Rafer Weigel Eric McCormack Audie England Patrick Van Horn Jonathan Slavin Phil LaMarr William Shatner Deborah Van Valkenburgh
writer director nerd william shatner lighthearted offbeat theater bar apartment los angeles ambition success regret hero worship obsession underdog growing up quest 1990s
Two less than successful film producers, approaching mid-life crisis and clinging to their nerdy sci-fi obsessions, suddenly meet their idol: William Shatner.
7.1/10
Comedy
USA|France|Germany|Japan|Italy|Spain
1992
93 Minutes
Steve Buscemi Seymour Cassel Jennifer Beals Pat Moya Will Patton Sully Boyer Steven Randazzo Francesco Messina Jim Jarmusch Carol Kane Stanley Tucci
writer neighbor con artist producer actor director offbeat playful witty gritty new york city apartment restaurant street film set aspirations filmmaking unrequited love unlikely allies petty crime
New Yorker Adolpho Rollo is your classic head-movie auteur. In his mind, he's creating deathless classics of the screen. Back in the real world, he can't pay the rent on the downtown grothole he calls home.
7.2/10
Comedy, Drama
USA
1987
100 Minutes
Mickey Rourke Faye Dunaway Alice Krige Jack Nance J.C. Quinn Frank Stallone Sandy Martin Roberta Bassin
writer drunk bartender barfly woman publisher gritty hedonistic cheeky emotional los angeles bar street apartment parking lot alcoholism poetry misfits drinking fighting
Based on the life of successful poet Charles Bukowski and his exploits in Hollywood during the 60s, 70s, and 80s.
6.1/10
Comedy, Drama
France|UK
2000
94 Minutes
Saïd Taghmaoui Juliette Lewis Rupert Graves Anna Massey Clémentine Célarié Karim Belkhadra
immigrant screenwriter photographer impersonator student blind woman lighthearted witty campy offbeat london restaurant rooming house dance studio nightclub england immigration poverty marriage of convenience ambition
Ali is a young Egyptian screenwriter determined to succeed in London, where he has been a student. He loves the artistic and political freedom, the colours, the music, the individualism. ... See full summary »
5.9/10
Comedy
USA
2016
112 Minutes
Ice Cube Cedric Kyles Regina Hall Sean Patrick Thomas Eve Anthony Anderson Jazsmin Lewis JB Smoove Common Nicki Minaj Lamorne Morris
barber stylist co-worker client son gang member cheeky emotional creative barbershop apartment street bar car police station hard times bonding gangs conversation neighborhood watch
As their surrounding community has taken a turn for the worse, the crew at Calvin's Barbershop come together to bring some much needed change to their neighborhood.
6.6/10
Comedy, Drama
Norway|USA|Germany|France|Italy
2005
93 Minutes
Matt Dillon Lili Taylor Marisa Tomei Fisher Stevens Adrienne Shelly Karen Young Tom Lyons Didier Flamand
writer deadbeat stripper publisher gritty los angeles apartment bar alcoholism obsession writing odd jobs gambling quest wretched excess 1940s
This drama centers on Hank Chinaski, the fictional alter-ego of "Factotum" author Charles Bukowski, who wanders around Los Angeles, CA trying to live off jobs which don't interfere with his primary interest, which is writing. Along the way, he fends off the distractions offered by women, drinking and gambling.
5.6/10
Comedy, Drama, Gay & Lesbian
USA
1997
86 Minutes
Douglas Spain Efrain Figueroa Kandeyce Jensen Martha Velez Lysa Flores Annette Murphy Robin Thomas Vincent Chandler Al Vincente Herbert Siguenza Jeff Michalski
pimp male prostitute star producer father melodramatic emotional offbeat amusing los angeles street mansion studio prostitution career ambition family business poverty growing up quest
After five years of living in Mexico, Carlos, an 18-year-old youth returns to Los Angeles. He wants to be an actor. But his father, Pepe, a pimp wants him to work in the family business, ... See full summary »
6.7/10
Comedy
Canada
1985
80 Minutes
John Paizs Eva Kovacs Neil Laurie Darrell Baran Jeffrey Owen Madden Tea Andrea Tanner Mark Yuill Neil Lawrie
screenwriter neighbor partner texan boarder young girl amusing offbeat campy emotional family home street canada rented room texas screenwriting writer's block opposites attract obsession unusual friendship
A young director intent on making "the greatest color crime movie ever" can't seem to finish his script--he has a beginning and an end, but he can't quite figure out the middle. The ... See full summary »
7.8/10
Comedy, Adventure, Fantasy
USA
1984
107 Minutes
Bill Murray Dan Aykroyd Harold Ramis Sigourney Weaver Rick Moranis Annie Potts William Atherton Ernie Hudson
parapsychologist love interest nerd supernatural being ghost secretary hilarious eerie amusing new york city firehouse apartment library city apartment college campus ghosts demonic possession supernatural daunting task showdown
Three former parapsychology professors set up shop as a unique ghost removal service.
7.5/10
Mystery & Thriller, Documentary, Comedy
USA
2002
97 Minutes
Paige Kimble Jonathan Knisely Balu Natarajan Julianne Ruth
child parent teacher announcer reporter uplifting charming inspiring hotel washington, d.c. family home spelling bee success competition class distinctions childhood family rivalry quest underdog
Spellbound follows eight teenagers on their quest to win the 1999 National Spelling Bee.
7.4/10
Comedy, Drama
France|Germany|USA
2016
118 Minutes
Adam Driver Golshifteh Farahani Barry Shabaka Henley Cliff "Method Man" Smith Chasten Harmon William Jackson Harper Masatoshi Nagase Sterling Jerins Rizwan Manji
bus driver passenger dog bartender wife writer calm emotional heartwarming inspiring profound new jersey bus bar house small-town life writing working class work-life balance discovery
A quiet observation of the triumphs and defeats of daily life, along with the poetry evident in its smallest details.
7.2/10
Gay & Lesbian, Comedy
USA
2019
102 Minutes
Kaitlyn Dever Beanie Feldstein Jessica Williams Jason Sudeikis Lisa Kudrow Will Forte Victoria Ruesga Mason Gooding Skyler Gisondo Diana Silvers Molly Gordon
teenager best friend overachiever classmate teacher principal offbeat unrestrained hilarious amusing emotional touching high school party house classroom graduation family home teenage rebellion overcoming fears
On the eve of their high school graduation, two academic superstars and best friends realize they should have worked less and played more. Determined not to fall short of their peers, the girls try to cram four years of fun into one night.
7.1/10
Comedy, Kids & Family
USA
2011
98 Minutes
Jason Segel Amy Adams Chris Cooper Rashida Jones Alan Arkin Donald Glover Ken Jeong Zach Galifianakis Sarah Silverman Emily Blunt
kermit the frog miss piggy oil baron fan young man young woman amusing witty madcap charming los angeles mansion theater santa barbara, calif. fame greed friendship second chance the muppets adventure
A Muppet fanatic with some help from his 2 human compatriots must regroup the Muppet gang to stop an avaricious oil mogul from taking down one of their precious life-longing treasures.
7.0/10
Comedy, Drama
France
1996
99 Minutes
Jean-Pierre Léaud Nathalie Richard Antoine Basler Nathalie Boutefeu Bulle Ogier Lou Castel Arsinée Khanjian Alex Descas Dominique Faysse Bernard Nissile Olivier Torres
director maggie cheung costume designer crew member journalist actress witty creative crafty offbeat france movie set hotel theater vacation home filmmaking life imitating art culture clash unrequited love failing career
A Chinese movie actress, in France to star in a remake of "Les Vampires", finds petty intrigues and clashing egos on the set.
7.3/10
Comedy
USA
1993
105 Minutes
Woody Allen Diane Keaton Alan Alda Anjelica Huston Jerry Adler Lynn Cohen Ron Rifkin Joy Behar Marge Redmond Aida Turturro
husband wife son writer amateur sleuth neighbor amusing playful new york city apartment restaurant movie theater city apartment big city murder investigation marriage romance death city life suspicion
A middle-aged couple suspects foul play when their neighbor's wife suddenly drops dead.
5.6/10
Musical, Comedy
USA
1939
93 Minutes
Vera Zorina Eddie Albert Alan Hale Leonid Kinskey Frank McHugh James Gleason Gloria Dickson Queenie Smith Erik Rhodes Berton Churchill
composer ballerina director partner patroness hit man amusing lighthearted new york city university hotel bar theater music ballet vaudeville jealousy assassination quest rise
A young hoofer quits vaudeville to become a composer and hooks up with a Russian ballet troupe.
6.9/10
Comedy
Canada
1999
97 Minutes
Liane Balaban Tara Spencer-Nairn Andrew McCarthy Mary Walsh Nicholas Campbell Cathy Moriarty Kevin Curran Krista MacDonald Cassie MacDonald
teen girl misfit newcomer teacher mother father winsome passionate amusing hedonistic nova scotia cape breton island seaside school canada small town boxing art ambition friendship
A gifted teenager dreaming of life beyond her small town becomes inspired when a 15-year-old girl from New York moves in next door.
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.
7.2/10
Comedy, Romance, Drama
Italy|UK|USA
1992
105 Minutes
Robert John Burke Bill Sage Karen Sillas Elina Lowensohn Martin Donovan Mark Chandler Bailey Chris Cooke Jeffrey Howard Holly Marie Combs Joe Stevens
thief brother pretty woman father friend epileptic witty cool offbeat cheeky new york city long island, n.y. bar apartment reunion journey siblings dangerous romance betrayal fugitives
Bitter about being double-crossed by the women he loved, (and with the police after him to boot), Bill vows to seduce the next woman he sees, then throw her away. His brother Dennis, ... See full summary »
7.6/10
Comedy
USA
1968
88 Minutes
Zero Mostel Gene Wilder Dick Shawn Kenneth Mars Estelle Winwood Christopher Hewett Andreas Voutsinas Lee Meredith Renee Taylor Frank Campanella
producer accountant playwright actor director hippie hilarious cheeky charming office theater courtroom prison broadway theater theater production nazism scams shady dealings quest fall
A stage-play producer devises a plan to make money by producing a sure-fire flop.
7.8/10
Comedy, Drama
USA
1983
101 Minutes
Robert De Niro Jerry Lewis Sandra Bernhard Diahnne Abbott Shelley Hack Lou Brown Margo Winkler
comedian stalker talk show host mother friend offbeat amusing wild basement new york city country house celebrity obsession stalking kidnapping determination ambition quest underdog rise
Rupert Pupkin is a passionate yet unsuccessful comic who craves nothing more than to be in the spotlight and to achieve this, he stalks and kidnaps his idol to take the spotlight for himself.
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