Movies Like Wanda Sykes: Legacy

If you liked Wanda Sykes: Legacy (2026), a comedy movie directed by Julie Dash, 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
Dave Chappelle: The Dreamer (2023)
★ 6.9/10Also comedy
From his onstage tackle to the slap heard round the world, Dave Chappelle lets loose in this freewheeling and unfiltered stand-up comedy special.
2
Jimmy Carr: Natural Born Killer (2024)
★ 6.4/10Also comedy
Jimmy Carr refutes the idea that you can't joke about anything these days with his edgy takes on gun control, religion, cancel culture and consent.
3
Shane Gillis: Beautiful Dogs (2023)
★ 7/10Also comedy
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.
4
Richard Pryor: Live in Concert (1979)
★ 7.4/10Also comedy
Richard Pryor delivers monologues on race, sex, family and his favorite target—himself, live at the Terrace Theatre in Long Beach, California.
5
Me Time (2022)
★ 5.8/10Also comedy
With his family away, a devoted stay-at-home dad enjoys his first me time in years by joining his hard-partying old friend on a wild birthday adventure.
6
Chris Rock: Bigger & Blacker (1999)
★ 7.4/10Also comedy
Chris Rock brings his critically acclaimed brand of social commentary-themed humour to this HBO Special, extolling his razor-sharp wit and wisdom on such topics as gun control, President Clinton, homophobia, racism…
7
Bill Burr: Drop Dead Years (2025)
★ 7.2/10Also comedy
In what might be his most personal and introspective hour yet, Bill offers hilarious takes on everything from male sadness to dating advice.
8
Spa Weekend (2026)
★ 6.5/10Also comedy
Four lifelong friends realize that somewhere between careers, relationships, families, and everyday responsibilities, they’ve forgotten how to take care of themselves and each other. Burned out and overdue for a break…
9
Chris Rock: Selective Outrage (2023)
★ 6.2/10Also comedy
Chris Rock delivers an electric stand-up set on non-racist yoga pants, spoiling his kids, the Kardashians and his thoughts on the Will Smith fiasco.
10
Dave Chappelle: Sticks & Stones (2019)
★ 7.5/10Also comedy
Dave Chappelle takes on gun culture, the opioid crisis and the tidal wave of celebrity scandals in this defiant stand-up special.
11
Adam Sandler: Love You (2024)
★ 6.3/10Also comedy
Adam Sandler hits the stage for a thrillingly unpredictable comedy special featuring songs, jokes, party-crashing dogs and plenty of love.
12
The Railrodder (1965)
★ 6.8/10Also comedy
After literally swimming across the Atlantic Ocean, an Englishman takes a country trip across Canada on a railcar.
13
Amazon Women on the Moon (1987)
★ 5.9/10Also comedy
Centered on a television station which features a 1950s-style sci-fi movie interspersed with a series of wild commercials, wacky shorts and weird specials, this lampoon of contemporary life and pop culture skewers some…
14
Wanda Sykes: Not Normal (2019)
★ 7/10Also comedy
Wanda Sykes tackles politics, reality TV, racism and the secret she'd take to the grave in this rollicking, no-holds-barred stand-up special.
15
Die, Mommie, Die! (2003)
★ 6.6/10Also comedy
Angela Arden is a washed up, has-been singing star who is trapped in a hateful marriage to film producer Sol Sussman. In an attempt to escape her marriage so that she can be with a hunky layabout, she poisons her…
16
Hard to Die (1990)
★ 6/10Also comedy
While doing the inventory for a lingerie outlet in a high rise office building, five attractive women are terrorized by a series of bizarre killings. They suspect that the strange janitor, who witnessed another series…
17
Between Two Ferns: The Movie (2019)
★ 5.9/10Also comedy
Galifianakis dreamed of becoming a star. But when Will Ferrell discovered his public access TV show, 'Between Two Ferns' and uploaded it to Funny or Die, Zach became a viral laughing stock. Now Zach and his crew are…
18
Demetri Martin: The Overthinker (2018)
★ 6.8/10Also comedy
With his signature one-liners and drawings, Demetri Martin muses on doughnut holes, dogs, sports bars, the alphabet's most aggressive letters and more.
19
Amy Schumer: Live at the Apollo (2015)
★ 5.8/10Also comedy
With her unique blend of honesty and unapologetic humor, Amy Schumer is one of the funniest, freshest faces in the industry today. This October, Schumer's provocative and hilariously wicked mind will be on full display…
20
Life of the Party (2018)
★ 6.1/10Also comedy
When her husband suddenly dumps her, longtime dedicated housewife Deanna turns regret into re-set by going back to college... landing in the same class and school as her daughter, who's not entirely sold on the idea…