Movies Like My Weekend as a 28-Year-Old in Chicago

If you liked My Weekend as a 28-Year-Old in Chicago (2022), a comedy movie directed by Judd Crud, 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 Good, the Bart, and the Loki (2021)
★ 7.2/10Also comedy
Loki is banished from Asgard once again and must face his toughest opponents yet: the Simpsons and Springfield’s mightiest heroes. The God of Mischief teams up with Bart Simpson in the ultimate crossover event paying…
2
A Knight for a Day (1946)
★ 6.6/10Also comedy
By accident, Cedric (Goofy), replaces his master, Sir Loinsteak, in the armor just before the joust with champion Sir Cumference.
3
Gabriel Iglesias: I'm Sorry for What I Said When I Was Hungry (2016)
★ 7/10Also comedy
Hawaiian-shirt enthusiast Gabriel "Fluffy" Iglesias finds the laughs in racist gift baskets, Prius-driving cops and all-female taco trucks.
4
Baseball Bugs (1946)
★ 6.9/10Also comedy
Bugs Bunny single handedly takes on the “Gas-House Gorillas,” a baseball team of hulking, cigar-chomping bullies.
5
Solid Serenade (1946)
★ 7.4/10Also comedy
Tom ties up Spike and sneaks into the courtyard of the glamorous Toodles Galore with his bass, hoping to woo her with his song, much to the annoyance of a sleeping Jerry.
6
2 Minutes of Fame (2020)
★ 6.6/10Also comedy
An up-and-coming stand-up comic moves to L.A. to pursue a film career after video clips of his act make him an online sensation.
7
Weird Science (1985)
★ 6.5/10Also comedy
Two unpopular teenagers, Gary and Wyatt, fail at all attempts to be accepted by their peers. Their desperation to be liked leads them to "create" a woman via their computer. Their living and breathing creation is a…
8
Monty Python Live at the Hollywood Bowl (1982)
★ 7.4/10Also comedy
Monty Python perform many of their greatest sketches at the Hollywood Bowl, including several from pre-Python days.
9
The Mouse That Roared (1959)
★ 6.4/10Also comedy
The Duchy of Grand Fenwick decides that the only way to get out of their economic woes is to declare war on the United States, lose and accept foreign aid. They send an invasion force (in chain mail, armed with bows…
10
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.
11
Tokyo Mater (2008)
★ 6.3/10Also comedy
A routine tow lands Mater in Tokyo, where he is challenged to a drift-style race against a nefarious gang leader and his posse of ninjas. With the help of his friend, 'Dragon' Lightning McQueen, and some special…
12
Red Hot Riding Hood (1943)
★ 7.3/10Also comedy
Tired of always playing the same roles, Little Red Riding Hood, her grandmother and the Wolf demand a new version of the tale. The story then plays out in a more contemporary urban environment, with Little Red Riding…
13
The Big Bad Wolf (1934)
★ 6.5/10Also comedy
The Big Bad Wolf torments Little Red Riding Hood and the Three Little Pigs.
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
Sufferin' Cats! (1943)
★ 7.1/10Also comedy
Tom fights with another cat over Jerry.
16
Chris Rock: Selective Outrage (2023)
★ 6.2/10Also comedy
Chris Rock delivers an electric stand-up set on non-racist yoga pants, spoiling his kids, the Kardashians and his thoughts on the Will Smith fiasco.
17
Three Little Pigs (1933)
★ 6.9/10Also comedy
The two pigs building houses of hay and sticks scoff at their brother, building the brick house. But when the wolf comes around and blows their houses down (after trickery like dressing as a foundling sheep fails)…
18
South Park (Not Suitable for Children) (2023)
★ 7.4/10Also comedy
After it's discovered that a teacher at South Park Elementary has an OnlyFans page, Randy is compelled to take a closer look at the seedy underbelly of the world of online influencers.
19
Sea Scouts (1939)
★ 6.4/10Also comedy
Donald is an admiral on a seagoing voyage with his nephews in which they encounter a ravenous shark.
20
Jim Gaffigan: Beyond the Pale (2006)
★ 7/10Also comedy
The affable, towheaded comic demonstrates his hysterical brand of self-effacing comedy and deadpan delivery at two sold-out shows at Chicago's Vic Theater. It's OK to laugh at this pale white guy...'cause nobody's…