Movies Like Free Wheeling

If you liked Free Wheeling (2005), a comedy and tv movie movie, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
Clear History (2013)
★ 6.1/10Also comedy and tv movie
Nathan Flomm, in order to avoid the humiliation of having missed out on a hugely successful business, assumes a new identity on Martha's Vineyard. He plots revenge when his former business partner moves to the same town.
2
Jack Whitehall: I'm Only Joking (2020)
★ 6.2/10Also comedy and tv movie
Jack Whitehall hits the stage with hilarious tales about happy couples, life in hotels, human stupidity and his well-traveled father.
3
Demetri Martin: The Overthinker (2018)
★ 6.8/10Also comedy and tv movie
With his signature one-liners and drawings, Demetri Martin muses on doughnut holes, dogs, sports bars, the alphabet's most aggressive letters and more.
4
Parade (1974)
★ 5.9/10Also tv movie and comedy
The story of a big party during which Jacques Tati brings together audience members, performers, clowns, children, and himself.
5
Robin Williams: An Evening at the Met (1986)
★ 8.2/10Also comedy and tv movie
In this hilarious stand up comedy, Robin Williams is energetic, witty and again hilarious. It's the number one stand up comedy of all time.
6
Gabriel Iglesias: Hot and Fluffy (2007)
★ 7.6/10Also comedy and tv movie
Gabriel Iglesias is one of the fastest-rising comics today! With his unique brand of humor, lovable stage presence and wide range of voices and impressions, it's no wonder that he already has a huge fan following. Now…
7
Gabriel Iglesias: Aloha Fluffy (2013)
★ 7.1/10Also comedy and tv movie
ALOHAAAAA! Internationally acclaimed comedian, Gabriel Iglesias, returns to Comedy Central with his latest stand-up special taped at Honolulu’s Hawaii Theatre Center. Watch as Fluffy brings the house down yet again in…
8
Trevor Noah: I Wish You Would (2022)
★ 6.9/10Also comedy and tv movie
Emmy-winning comedian Trevor Noah talks learning German, speaking ill of the dead, judging people in horror movies and ordering Indian food in Scotland.
9
Superwho? (2022)
★ 6.3/10Also comedy
A struggling actor seems doomed to live life as a loser. When he finally snatches a lead role as a superhero named “Badman,” he feels like everything is possible, but fate strikes again.
10
Ricky Gervais: Mortality (2025)
★ 7/10Also comedy and tv movie
Ricky Gervais tackles life, death and the state of the world in a brutally honest special that spares no topic, even his own mortality.
11
Bill Burr: Drop Dead Years (2025)
★ 7.2/10Also comedy and tv movie
In what might be his most personal and introspective hour yet, Bill offers hilarious takes on everything from male sadness to dating advice.
12
iParty with Victorious (2011)
★ 7.3/10Also comedy and tv movie
Scorned girlfriends Carly and Tori hatch a plot against the boy that they are both dating.
13
Click & Collect (2018)
★ 6.6/10Also comedy and tv movie
To save his daughter's Christmas, Andrew goes on a road trip with Dev, his neighbour from hell, to buy an elusive Sparklehoof the Unicorn Princess.
14
Shane Gillis: Beautiful Dogs (2023)
★ 7/10Also comedy and tv movie
In a rowdy stand-up set, Shane Gillis riffs on his girlfriend's Navy SEAL ex, touring George Washington's house and being bullied by an Australian Goth.
15
Lucky Luke: The Ballad of the Daltons (1978)
★ 6.8/10Also comedy
The Dalton brothers are to receive their dead uncle's fortune if they eliminate the judge and jury responsible for his execution. And to accomplish this task, they must enlist the help of Lucky Luke.
16
Dave Chappelle: Sticks & Stones (2019)
★ 7.5/10Also comedy and tv movie
Dave Chappelle takes on gun culture, the opioid crisis and the tidal wave of celebrity scandals in this defiant stand-up special.
17
Don't Die Too Hard! (2001)
★ 6.3/10Also comedy
Eric and Ramzy are working as window washers at the Montparnasse skyscraper in Paris. Thinking that he has a date set up with beautiful executive Marie-Joelle (who in reality hates his guts), Ramzy stays at work late…
18
Taylor Tomlinson: Quarter-Life Crisis (2020)
★ 7.2/10Also comedy and tv movie
Comedian Taylor Tomlinson is halfway through her 20s — and she's over it. From dating losers to a failed engagement, she takes aim at her life choices.
19
Hold-up (1985)
★ 6.2/10Also comedy
Dressed as a clown, the clever rascal Grimm holds up the most secure bank of Montreal and takes 30 hostages. While confusing and ridiculing the police with his strange behavior, he calmly manages to rid the bank of a…
20
The Speech (2020)
★ 6.3/10Also comedy
Meet Adrien! He's 35. He's stuck in a mid-life crisis. He's neurotic and hypochondriac. Tonight he's stuck in an endless family dinner and his girlfriend is not answering his texts. On top of that, his dumb…