Movies like My Weekend as a 28-Year-Old in Chicago (2022)
The best movies like My Weekend as a 28-Year-Old in Chicago (2022) are The Good, the Bart, and the Loki (2021), A Knight for a Day (1946) and 2 Minutes of Fame (2020). If My Weekend as a 28-Year-Old in Chicago hooked you with its comedy, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedRicky Gervais: SuperNature (2022)7.4/10 from 385 votes
- NewestRicky Gervais: Mortality (2025)Released 2025
The Good, the Bart, and the Loki (2021)
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 tribute to the Marvel Cinematic Universe of superheroes and villains.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisA Knight for a Day (1946)
By accident, Cedric (Goofy), replaces his master, Sir Loinsteak, in the armor just before the joust with champion Sir Cumference.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like this2 Minutes of Fame (2020)
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.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisZach Galifianakis: Live at the Purple Onion (2007)
From an inauspicious beginning performing comedy routines in the back of a burger joint in New York, unorthodox stand-up star Zach Galifianakis has made a splash on the scene with his inimitable brand of humor. In this live show filmed at San Francisco's Purple Onion nightclub, the versatile funnyman serves up a healthy dose of his signature wit.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisKevin Hart: I'm a Grown Little Man (2009)
Fresh off the heels of appearing in movies like Superhero Movie and The 40 Year-Old Virgin, fast-talking comedian Kevin Hart stars in this live stand-up performance where he makes fun of everything and everybody - especially himself.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisRed Hot Riding Hood (1943)
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 Hood working as a pin-up girl in a night club.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisJim Gaffigan: Beyond the Pale (2006)
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 laughing at Jim Gaffigan harder than Jim Gaffigan!
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisRicky Gervais: SuperNature (2022)
With his signature pitch-black sense of humor, Ricky Gervais takes the stage at the London Palladium in this provocative stand-up comedy special.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisHow to Irritate People (1969)
A pre-Monty Python mockumentary, written by and presented by John Cleese, that provides tips on learning how to irritate people.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisGabriel Iglesias: I'm Sorry for What I Said When I Was Hungry (2016)
Hawaiian-shirt enthusiast Gabriel "Fluffy" Iglesias finds the laughs in racist gift baskets, Prius-driving cops and all-female taco trucks.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisChris Rock: Selective Outrage (2023)
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.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisRicky Gervais: Out of England 2 (2010)
The comic performs at the Chicago Theatre.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisAdam Sandler: Love You (2024)
Adam Sandler hits the stage for a thrillingly unpredictable comedy special featuring songs, jokes, party-crashing dogs and plenty of love.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Rutles: All You Need Is Cash (1978)
The story of the rise and fall of the Pre-Fab Four.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisWeird Science (1985)
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 gorgeous woman, Lisa, whose purpose is to boost their confidence level by putting them into situations which require Gary and Wyatt to act like men.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisTokyo Mater (2008)
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 modifications, Mater attempts to drift to victory and become Tow-ke-O Mater, King of all Drifters.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisMonty Python Live at the Hollywood Bowl (1982)
Monty Python perform many of their greatest sketches at the Hollywood Bowl, including several from pre-Python days.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisDave Chappelle: For What It's Worth (2004)
Comedian Dave Chappelle does what he does best in this outrageous and hilarious standup performance, which allows him to push the envelope far beyond what he does on his TV show. Taped in San Francisco at the famed Fillmore, Chappelle lets loose on such topics as black celebrities, what it's like to have raunchy fans of his TV show approach him while he's trying to enjoy Disneyland with his kids, Michael Jackson, Kobe Bryant... and crackheads, of course. It's comedy Chappelle-style and, for what it's worth, no one is safe from his barbs. But you already knew that!
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisThe Mouse That Roared (1959)
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 and arrows) to New York and they arrive during a nuclear drill that has cleared the streets.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisRicky Gervais: Mortality (2025)
Ricky Gervais tackles life, death and the state of the world in a brutally honest special that spares no topic, even his own mortality.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisIndústrias Reunidas Machiavelli (2019)
Agripino and Sandoval roam around their workplace, Machiavelli Incorporated, a venture which they plan to expand whatever the costs.
Why it matches: Similar story and style · both comedy
VeggieTales: Lord of the Beans (2005)
Sunday morning values, Saturday morning fun! It’s a tale of good versus evil with beans! Lord of the Beans follows the fantastic journey of a Flobbit named Toto Baggypants (Junior Asparagus) who inherits a most unusual and powerful bean. With the help of his mentor Randall and a spirited group of friends, Toto embarks on a mission to discover how he should use his gift. On their quest, the group encounters many challenges, including crossing the mountains of Much-Snowia, and facing the dreaded Lord Scaryman – who seeks the bean for misguided, selfish reasons. Will Toto discover the purpose of his giver, or will the scary dude and his Spark army capture the bean and wield its awesome powers?
Why it matches: Similar story and style · both comedy
Piss (2010)
Kurtis Conner and his friends embark on a pissy adventure through the piss forest to find Prague and Lucifer to see how particular he actually is about his cheese.
Why it matches: Similar story and style · both comedy
The Buyer of the Harp (2009)
Short film by Bette Bentley.
Why it matches: Similar story and style · both comedy
VeggieTales: Tomato Sawyer & Huckleberry Larry's Big River Rescue (2008)
Meet Tomato Sawyer and Huckleberry Larry a two friends homesteading along the banks of the mighty Mississippi River. Tom and Huck look forward to owning their own land, building a home and opening Huckas Jerkyland and Tomas Tax Preparation. But everything changes when they meet a mysterious stranger who is on the run and trying to find his mama. Will Huck and Tom risk losing all theyave worked for in order to help someone they hardly know? Find out in this exciting river rescue that reminds kids of the importance of helping others.
Why it matches: Similar story and style · both comedy
A Night On The Tiles (2005)
The film follows the shenanigans of the goings on in the male and female toilets of a local nightclub. We meet the two young toilet attendants who have more interest in each other than the events of the evening.
Why it matches: Similar story and style · both comedy
School Safari (2005)
In this film, we meet Jack who is inspired by his Uncle Bob - who he believes to be an explorer in Africa. Jack starts to see the world around him and all those in it, just as if he were out on safari in the Serengeti!
Why it matches: Similar story and style · both comedy
Manivald (2018)
Manivald is a fox in his early 30s. He is still living at home with his mother. One day a young hot wolf called Toomas comes to fix the washing machine. A love triangle develops between the three of them. Things get out of hand and Manivald realizes that it is time to move out.
Why it matches: Similar story and style · both comedy
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Frequently asked questions
What are the best movies like My Weekend as a 28-Year-Old in Chicago?
The closest matches to My Weekend as a 28-Year-Old in Chicago are The Good, the Bart, and the Loki (2021), A Knight for a Day (1946) and 2 Minutes of Fame (2020). Below are 27 more, each with the reason it matches.
What should I watch after My Weekend as a 28-Year-Old in Chicago?
Start with The Good, the Bart, and the Loki (2021), the closest match to My Weekend as a 28-Year-Old in Chicago.
What is the highest-rated movie like My Weekend as a 28-Year-Old in Chicago?
Ricky Gervais: SuperNature (2022), rated 7.4/10 by 385 TMDB users.
What is the newest movie like My Weekend as a 28-Year-Old in Chicago?
Ricky Gervais: Mortality (2025) is the most recent release on this list.
Are there English movies like My Weekend as a 28-Year-Old in Chicago?
Yes: The Good, the Bart, and the Loki (2021), A Knight for a Day (1946) and 2 Minutes of Fame (2020).
How are movies similar to My Weekend as a 28-Year-Old in Chicago chosen?
First come films that Trakt’s viewers watch alongside My Weekend as a 28-Year-Old in Chicago, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.