Movies Like The First $20 Million Is Always the Hardest

If you liked The First $20 Million Is Always the Hardest (2002), a comedy movie directed by Mick Jackson, 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
The Brass Teapot (2012)
★ 6.1/10Also comedy
When a couple discovers that a brass teapot makes them money whenever they hurt themselves, they must come to terms with how far they are willing to go.
2
The Big Hit (1998)
★ 6/10Also comedy
Affable hit man Melvin Smiley is constantly being scammed by his cutthroat colleagues in the life-ending business. So, when he and his fellow assassins kidnap the daughter of an electronics mogul, it's naturally Melvin…
3
John Mulaney: Kid Gorgeous at Radio City (2018)
★ 7.9/10Also comedy
John Mulaney relays stories from his childhood and "SNL," eviscerates the value of college and laments getting older in this electric comedy special.
4
Mickey 17 (2025)
★ 6.8/10Also comedy
Unlikely hero Mickey Barnes finds himself in the extraordinary circumstance of working for an employer who demands the ultimate commitment to the job… to die, for a living.
5
Jay and Silent Bob Strike Back (2001)
★ 6.3/10Also comedy
When Jay and Silent Bob learn that their comic-book alter egos, Bluntman and Chronic, have been sold to Hollywood as part of a big-screen movie that leaves them out of any royalties, the pair travel to Tinseltown to…
6
Good Luck, Have Fun, Don't Die (2026)
★ 7.1/10Also comedy
A 'Man from the Future' arrives at an LA diner where he must recruit the precise combination of disgruntled patrons to join him on a one-night quest to save the world from the terminal threat of a rogue artificial…
7
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…
8
Drive (1997)
★ 6.2/10Also comedy
A prototype enhanced human, on the run from Chinese-hired hit men, hooks up with a dread-locked bystander, and the two of them elude their pursuers narrowly each time.
9
Babes (2024)
★ 6/10Also comedy
After getting pregnant from a one-night stand, a single woman leans on her married best friend and mother of two to guide her through gestation and beyond.
10
The Bed Sitting Room (1969)
★ 5.9/10Also comedy
In the hazy aftermath of World War III, the fallout from a 'nuclear misunderstanding' is producing strange mutations amongst the survivors, and the noble Lord Fortnum finds himself transforming into a bed sitting room.
11
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…
12
21 & Over (2013)
★ 5.8/10Also comedy
Brilliant student Jeff Chang has the most important interview of his life tomorrow. But today is still his birthday, what starts off as a casual celebration with friends evolves into a night of debauchery that risks to…
13
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.
14
Eddie Izzard: Dress to Kill (1999)
★ 7.8/10Also comedy
Eddie 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…
15
Joy Ride (2023)
★ 6.5/10Also comedy
When Audrey's business trip to Asia goes sideways, she enlists the aid of Lolo, her irreverent, childhood best friend who also happens to be a hot mess; Kat, her college friend turned Chinese soap star; and Deadeye…
16
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.
17
American Reunion (2012)
★ 6.4/10Also comedy
The characters we met a little more than a decade ago return to East Great Falls for their high school reunion. In one long-overdue weekend, they will discover what has changed, who hasn’t, and that time and distance…
18
The Hangover Part III (2013)
★ 6.2/10Also comedy
This time, there's no wedding. No bachelor party. What could go wrong, right? But when the Wolfpack hits the road, all bets are off.
19
Ricky Gervais: Mortality (2025)
★ 7/10Also comedy
Ricky Gervais tackles life, death and the state of the world in a brutally honest special that spares no topic, even his own mortality.
20
Wet Hot American Summer (2001)
★ 6.2/10Also comedy
It's the last day of Camp Firewood's season, but there's still time for the big talent show, a little romance… and for everyone to be wiped out by the piece of NASA's Skylab that's hurtling toward Earth.