Movies Like Pretty Cool

If you liked Pretty Cool (2002), a fantasy and comedy movie directed by Rolfe Kanefsky, 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 F**k-It List (2020)
★ 6/10Also comedy
After a prank blows up a studious high school senior's life, he shares a list of certain things he wishes he'd done differently — and maybe still can.
2
Dr. Strange (1978)
★ 6/10Also fantasy
A psychiatrist becomes the new Sorcerer Supreme of the Earth in order to battle an evil Sorceress from the past.
3
Clear History (2013)
★ 6.1/10Also comedy
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.
4
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.
5
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…
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
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.
8
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.
9
Real Men (1987)
★ 6/10Also comedy
A womanizing CIA agent and an insecure insurance agent are paired together to make sure a deal goes through with aliens for the future of mankind.
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
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
Louis C.K.: Ridiculous (2026)
★ 6.1/10Also comedy
From a bee getting shot in New York City to paying strangers to take his aging father, Louis C.K. unleashes the ridiculous thoughts in his mind.
13
The Wedding Year (2019)
★ 5.9/10Also comedy
A commitment-phobic 27-year old’s relationship is put to the test when she and her boyfriend attend 7 weddings in the same year.
14
Marc Maron: End Times Fun (2020)
★ 6.7/10Also comedy
Marc Maron wades through a swamp of vitamin hustlers, evangelicals and grown male nerd children, culminating in a gleefully filthy end-times fantasy.
15
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…
16
Relax, I'm from the Future (2023)
★ 5.9/10Also comedy
Casper is a time traveller who arrives in the 2020s in an attempt to prevent a major future catastrophe. He meets Holly, a queer black woman he befriends and draws into his plan by giving her his knowledge of the…
17
Strawberry Mansion (2021)
★ 6.7/10Also fantasy
In the not-too-distant future, an all-seeing surveillance state conducts “dream audits” to collect taxes on the unconscious lives of the populace. Mild-mannered government agent James Preble travels to a remote…
18
Afterburn (2025)
★ 6.2/10Also comedy
Set against the backdrop of a postapocalyptic Earth whose Eastern Hemisphere was destroyed by a massive solar flare, leaving what life remains mutated from radiation and fallout. The story revolves around a group of…
19
Ladies First (2026)
★ 5.9/10Also comedy and fantasy
An arrogant but charismatic ladies' man finds his life of money, power and casual flings upended when he wakes up in a parallel world dominated by women.
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.