Movies Like Kim Congdon: Childless Milf

If you liked Kim Congdon: Childless Milf (2024), a comedy movie directed by Jack Higgins, 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
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.
2
Jim Jefferies: Freedumb (2016)
★ 7.2/10Also comedy
Returning for a second Netflix comedy special, Jim Jefferies unleashes his famously ferocious black humor to a packed house in Nashville, Tennessee.
3
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.
4
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.
5
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.
6
Driver's Ed (2026)
★ 6.9/10Also comedy
A group of teens hit the road in a stolen driver's ed car, racing against time to help a lovesick high school senior track down his college-freshman girlfriend and win her back.
7
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…
8
Jim Jefferies: Intolerant (2020)
★ 7.1/10Also comedy
Between scenes from an excruciating date, Jim Jefferies digs into generational differences, his own bad habits and the shifting boundaries in comedy.
9
Chris D'Elia: Man on Fire (2017)
★ 6.2/10Also comedy
Unbridled comic Chris D'Elia reconsiders his approach to major life events like marriage, not having kids and buying pants for your friends.
10
Fun with Dick and Jane (1977)
★ 6.6/10Also comedy
When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.
11
Ali Wong: Single Lady (2024)
★ 6.4/10Also comedy
After a whirlwind couple of years, Ali Wong returns to the stage to dish on the highs, lows and surprises of dating post-divorce.
12
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…
13
Gabriel Iglesias: I'm Sorry for What I Said When I Was Hungry (2016)
★ 7.1/10Also comedy
Hawaiian-shirt enthusiast Gabriel "Fluffy" Iglesias finds the laughs in racist gift baskets, Prius-driving cops and all-female taco trucks.
14
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.
15
Chris Rock: Never Scared (2004)
★ 7.5/10Also comedy
Chris 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…
16
Aziz Ansari: Live at Madison Square Garden (2015)
★ 6.5/10Also comedy
Ansari headlines the iconic Madison Square Garden and delivers his most hilarious and insightful stand-up yet. Filmed in front of a sold-out audience, Ansari's latest special is an uproarious document of the comic in…
17
One of Them Days (2025)
★ 6.7/10Also comedy
Best friends and roommates Dreux and Alyssa are about to have One of Them Days. When they discover Alyssa’s boyfriend has blown their rent money, the duo finds themselves going to extremes in a comical race against the…
18
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.
19
Kevin James: Never Don't Give Up (2018)
★ 6.2/10Also comedy
Kevin James makes his long-awaited return to stand-up in this family-friendly special, dishing on fatherhood, fans, his disdain for allergies and more.
20
Qwerty (2012)
★ 6.4/10Also comedy
Before introverted word-nerd Zoe gains the courage to enter the National Scrabble Championship, she meets her emotional match in Marty, an irascible recluse. She finds him equally pitted against the opposing forces in…