Movies Like Bill Bailey: Bewilderness

If you liked Bill Bailey: Bewilderness (2001), a comedy movie directed by John Kaye Cooper, 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
Taking Care of Business (1990)
★ 6.3/10Also comedy
An uptight advertising exec has his entire life in a filofax organizer which mistakenly ends up in the hands of a friendly convict who poses as him.
2
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.
3
Chris Tucker: Live (2015)
★ 6/10Also comedy
Comedian Chris Tucker performs live.
4
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.
5
American Dreamer (2022)
★ 6/10Also comedy
In this winsome comedy, an entitled Economics professor pursues a tactic to buy an ailing widow’s mansion for nothing, but he quickly realizes that his seemingly foolproof strategy won’t be as easy as he thought.
6
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.
7
Eddie Murphy: Delirious (1983)
★ 7.6/10Also comedy
Taped live and in concert at Constitution Hall in Washington, D.C. in August, 1983, Eddie Murphy: Delirious captures Eddie Murphy's wild and outrageous stand-up comedy act, which he performed in New York and eighteen…
8
Batman and Harley Quinn (2017)
★ 6.2/10Also comedy
Batman and Nightwing are forced to team with the Joker's sometimes-girlfriend Harley Quinn to stop a global threat brought about by Poison Ivy and Jason Woodrue, the Floronic Man.
9
Once Upon a Deadpool (2018)
★ 7.1/10Also comedy
A kidnapped Fred Savage is forced to endure Deadpool's PG-13 rendition of Deadpool 2, as a Princess Bride-esque story full of magic, wonder, and zero Fs.
10
Duplex (2003)
★ 6.1/10Also comedy
When a young couple buys their dream home, they have no idea what the sweet little old lady upstairs is going to put them through!
11
Private Valentine: Blonde & Dangerous (2008)
★ 6.2/10Also comedy
When fluffy, bubble gum movie star Megan Valentine suddenly finds herself broke and humiliated in the public eye, she wanders from the wreckage of a car accident and witlessly enlists in the U.S. Army hoping in vain…
12
Click & Collect (2018)
★ 6.6/10Also comedy
To save his daughter's Christmas, Andrew goes on a road trip with Dev, his neighbour from hell, to buy an elusive Sparklehoof the Unicorn Princess.
13
The Ladies Man (1961)
★ 6.3/10Also comedy
After his girl leaves him for someone else, Herbert gets really depressed and starts searching for a job. He finally finds one in a big house which is inhabited by many, many women. Can he live in the same home with…
14
Big Trouble (2002)
★ 6.1/10Also comedy
The story of how a mysterious suitcase brings together, and changes, the lives of a divorced dad, an unhappy housewife, two hitmen, a pair of street thugs, two love struck teens, two FBI men and a psychedelic toad…
15
Brain Donors (1992)
★ 6.1/10Also comedy
Three manic idiots—a lawyer, a cab driver and a handyman—team up to run a ballet company to fulfil the will of a millionaire. Stooge-like antics result as the trio try to outwit the rich widow and her scheming big-shot…
16
The Three Stooges (2012)
★ 5.8/10Also comedy
Left on the doorstep of an orphanage run by nuns, three newborn knuckleheads grow up to be finger-poking, nyuk-nyuking janitors named Larry, Curly and Moe. When they learn that financial problems will soon force the…
17
Yellow Mirror (2026)
★ 8.1/10Also comedy
A defective lamp reveals a heartbreaking truth about what Homer believes is reality, and an AI-powered tablet befriends and controls Maggie. The Simpsons struggle to find the light through two dark tales of the curious…
18
The Patsy (1964)
★ 6.2/10Also comedy
Eccentric bellhop Stanley Belt is recruited unexpectedly by the comedy team of a recently deceased entertainer. Stanley struggles to become a song-and-dance man as the team grooms him to become a star. But as the date…
19
The Million Pound Note (1954)
★ 7/10Also comedy
An impoverished American sailor is fortunate enough to be passing the house of two rich gentlemen who have conceived the crazy idea of distributing a note worth one million pounds. The sailor finds that whenever he…
20
Candy Cane Lane (2023)
★ 6/10Also comedy
Determined to win the neighborhood's annual Christmas decorating contest, family man Chris makes a pact with an elf to help him out-do the competition. However, the elf casts a spell bringing the twelve days of…