Movies Like Michael Ian Black: First Annual Retirement Special
If you liked Michael Ian Black: First Annual Retirement Special (2026), a comedy movie directed by Jack Vaughn and Charlie Fonville, 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
Sextuplets (2019)
★ 6.2/10Also comedyFather-to-be Alan is shocked to learn that he was born a sextuplet. With his newfound brother Russell riding shotgun, the duo sets out on a hilarious journey to reunite with their remaining long-lost siblings.
- 2
Trailer Park Boys: Don't Legalize It (2014)
★ 6.4/10Also comedyOut of jail and broke, Julian concocts an outrageously greasy scheme to get rich and, to make it even greasier, he will have to deliver his product to his arch-enemy, Cyrus, who’s waiting in Montreal to close the dirty…
- 3
Chris D'Elia: Man on Fire (2017)
★ 6.2/10Also comedyUnbridled comic Chris D'Elia reconsiders his approach to major life events like marriage, not having kids and buying pants for your friends.
- 4
Jim Jefferies: Freedumb (2016)
★ 7.2/10Also comedyReturning for a second Netflix comedy special, Jim Jefferies unleashes his famously ferocious black humor to a packed house in Nashville, Tennessee.
- 5
Bill Burr: Drop Dead Years (2025)
★ 7.2/10Also comedyIn what might be his most personal and introspective hour yet, Bill offers hilarious takes on everything from male sadness to dating advice.
- 6
29th Street (1991)
★ 6.9/10Also comedyAfter winning $6.2 million in the 1976 New York State Lottery, he is arrested for throwing rocks at a church. He then tells his story at the police station.
- 7
Easy Money (1983)
★ 6/10Also comedyTo inherit his mother-in-law's colossal fortune, a hard living gambling addict must change his unhealthy ways before it gets the best of him.
- 8
Richard Pryor: Live in Concert (1979)
★ 7.4/10Also comedyRichard Pryor delivers monologues on race, sex, family and his favorite target—himself, live at the Terrace Theatre in Long Beach, California.
- 9
American Dreamer (2022)
★ 6/10Also comedyIn this winsome comedy, an entitled Economics professor pursues a tactic to buy an ailing widow’s mansion for nothing, but he quickly realizes that his seemingly foolproof strategy won’t be as easy as he thought.
- 10
Aziz Ansari: Intimate Moments for a Sensual Evening (2010)
★ 6.8/10Also comedyAziz Ansari presents his highly anticipated debut hour long stand-up special. The critically acclaimed stand-up and actor (Parks and Recreation, Funny People) discusses topics ranging from sheets with fraudulent thread…
- 11
Eddie Izzard: Dress to Kill (1999)
★ 7.8/10Also comedyEddie Izzard takes her show to San Francisco to give a brief history of pagan and Christian religions, the building of Stonehenge, the birth of the Church of England and of Western empires, and the need for a European…
- 12
Ali G, Innit (1999)
★ 6.5/10Also comedyAli G travels throughout Britain, interviewing unsuspecting leaders and politicians.
- 13
Criminal (2004)
★ 6.2/10Also comedyNeeding a new partner capable of intricate cons, Richard Gaddis, recruits Rodrigo, a crook with a perfect poker face. The two plan a big-time scam: selling a fake Silver Certificate to currency collector William…
- 14
Seriously Single (2020)
★ 6.8/10Also comedyWhile her free-living bestie urges her to embrace singlehood, a commitment-craving social media expert can't stop following the life of a former love.
- 15
Duplex (2003)
★ 6.1/10Also comedyWhen a young couple buys their dream home, they have no idea what the sweet little old lady upstairs is going to put them through!
- 16
Room Service (1938)
★ 6.5/10Also comedyBroke Gordon Miller tries to land a backer for his new play while he has to deal with with the hotel manager trying to evict him and his cast.
- 17
The Mouse That Roared (1959)
★ 6.4/10Also comedyThe Duchy of Grand Fenwick decides that the only way to get out of their economic woes is to declare war on the United States, lose and accept foreign aid. They send an invasion force (in chain mail, armed with bows…
- 18
One Night at McCool's (2001)
★ 5.9/10Also comedyOn an ordinary night, in an ordinary part of town, a beautiful young woman walks into a bar. Her name is Jewel, and before long she is chatting to bartender Randy. The pair leave together, but he ends up getting into a…
- 19
Chris Rock: Never Scared (2004)
★ 7.5/10Also comedyChris Rock, the three-time Emmy Award-winner, comedian, actor, and host of HBO's acclaimed The Chris Show, stars in his fourth solo stand-up special for HBO, Chris Rock: Never Scared. Featuring his unique, insightful…
- 20
Dave Chappelle: The Dreamer (2023)
★ 6.9/10Also comedyFrom his onstage tackle to the slap heard round the world, Dave Chappelle lets loose in this freewheeling and unfiltered stand-up comedy special.