Movies Like Gregory: Diary of a Nutcase

If you liked Gregory: Diary of a Nutcase (1993), a comedy movie directed by Peter Richardson, here are 19 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
Dennis the Menace (1993)
★ 5.9/10Also comedy
Mr. Wilson's ever-present annoyance comes in the form of one mischievous kid named Dennis. But he'll need Dennis's tricks to uncover a collection of gold coins that go missing when a shady drifter named Switchblade Sam…
2
Psycho Therapy: The Shallow Tale of a Writer Who Decided to Write About a Serial Killer (2025)
★ 6.8/10Also comedy
A struggling writer in the midst of a divorce befriends a retired serial killer who incidentally becomes his marriage counselor by day, and killing counselor for his next book by night.
3
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.
4
The Pink Panther Strikes Again (1976)
★ 6.9/10Also comedy
Charles Dreyfus, who has finally cracked over inspector Clouseau's antics, escapes from a mental institution and launches an elaborate plan to get rid of Clouseau once and for all.
5
Thunderstruck (2012)
★ 6.2/10Also comedy
After NBA star Kevin Durant switches talent with 16 year old Brian, the teenager becomes the star of his high school team, but Durant starts struggling and eventually learns an important lesson.
6
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.
7
Seriously Single (2020)
★ 6.8/10Also comedy
While 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.
8
How to Eat Fried Worms (2006)
★ 6.2/10Also comedy
During the first day of his new school year, a fifth grade boy squares off against a bully and winds up accepting a dare that could change the balance of power within the class.
9
One Night at McCool's (2001)
★ 5.9/10Also comedy
On 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…
10
Hostile Takeover (2025)
★ 6.9/10Also comedy
Follows Pete, a professional hitman, as he faces a group of assassins after the boss of a crime syndicate suspects disloyalty due to his attendance at Workaholics Anonymous meetings.
11
How to Rob a Bank (2007)
★ 5.8/10Also comedy
Caught in the middle of a bank robbery, a slacker and a bank employee become the ones who arbitrate the intense situation.
12
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.
13
Psych 2: Lassie Come Home (2020)
★ 7/10Also comedy
After Santa Barbara Police Chief Carlton Lassiter is ambushed and left for dead, Shawn and Gus return to help him and find themselves embroiled in a case involving the personal, the professional – and even the…
14
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.
15
The Killer's Game (2024)
★ 6.4/10Also comedy
When top hitman Joe Flood is diagnosed with a terminal illness, he decides to take matters into his own hands – by taking a hit out on himself. But when the very hitmen he hired also target his ex-girlfriend, he must…
16
Rookie of the Year (1993)
★ 6.2/10Also comedy
When the cast comes off his once broken arm, a 12-year-old boy can throw a 100-mile-an-hour fastball, and the Chicago Cubs want him as their new pitcher.
17
Ali G, Innit (1999)
★ 6.5/10Also comedy
Ali G travels throughout Britain, interviewing unsuspecting leaders and politicians.
18
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.
19
Trailer Park Boys: Countdown to Liquor Day (2009)
★ 6.6/10Also comedy
Ricky, Julian and Bubbles are about to get out of jail, and this time, Julian vows to go straight, even open a legit business. Soon the Boys will all be rich. At least that's what they've told the parole board. But…