Movies Like Operation Cupcake

If you liked Operation Cupcake (2012), a comedy and tv movie movie directed by Bradford May, 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
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.
2
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.
3
How to Irritate People (1969)
★ 6.6/10Also comedy and tv movie
A pre-Monty Python mockumentary, written by and presented by John Cleese, that provides tips on learning how to irritate people.
4
Thunderstruck (2012)
★ 6.2/10Also comedy
After NBA star Kevin Durant switches talent with 16 year old Brian, the teenager becomes the star of his high school team, but Durant starts struggling and eventually learns an important lesson.
5
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.
6
Psych: The Movie (2017)
★ 7.2/10Also comedy and tv movie
The ambitious friends come together during the holidays after a mystery assailant targets one of their own. A comedic thrill-ride follows, as the wild and unpredictable Psych team pursues the bad guys, justice … and…
7
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.
8
Psych 3: This Is Gus (2021)
★ 6.9/10Also comedy and tv movie
In preparation for a shotgun wedding before the birth of Baby Guster, Shawn and Gus go rogue in an attempt to track down Selene’s estranged husband, as Lassiter grapples with the future of his career.
9
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.
10
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.
11
Marc Maron: End Times Fun (2020)
★ 6.7/10Also comedy and tv movie
Marc Maron wades through a swamp of vitamin hustlers, evangelicals and grown male nerd children, culminating in a gleefully filthy end-times fantasy.
12
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.
13
A Flintstones Christmas Carol (1994)
★ 6.8/10Also comedy and tv movie
Fred is cast as Ebenezer Scrooge in a stage adaption of the classic Christmas story, but is acting a bit stingy in real life.
14
The Trailer Park Boys Xmas Special (2004)
★ 6.9/10Also comedy and tv movie
In this holiday prequel, it’s 1997 and Sunnyvale Trailer Park is getting ready for the holiday season. Julian’s got a great idea to make money this Christmas, Ricky gets confused between God and Santa, and Bubbles…
15
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…
16
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.
17
Little Big League (1994)
★ 6/10Also comedy
When the owner of the Minnesota Twins passes away, he bequeaths the team to his preteen grandson. The newly minted head honcho quickly appoints himself manager, causing unrest in an organization that struggles to take…
18
Jack Whitehall: I'm Only Joking (2020)
★ 6.3/10Also 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.
19
Merry Christmas, Drake & Josh (2008)
★ 7.3/10Also comedy and tv movie
Step brothers Drake and Josh must give a foster family the best Christmas ever or face years in jail for a Christmas party gone wrong.
20
Jackass Presents: Bad Grandpa (2013)
★ 6.2/10Also comedy
86-year-old Irving Zisman is on a journey across America with the most unlikely companion: his 8 year-old grandson, Billy.