Movies Like Capturing Chicago

If you liked Capturing Chicago (1916), a comedy movie, 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 Flying Car (2002)
★ 6.7/10Also comedy
Stuck in a traffic jam, Dante and Randal discuss the prospect of a flying car.
2
Louis C.K.: Oh My God (2013)
★ 7.6/10Also comedy
Filmed at the Celebrity Theatre in Phoenix, AZ on February 15th and 16th, 2013, Oh My God is Louis C.K.'s fifth stand-up special, his first for HBO since 2007's Shameless, and his first since winning a Emmy Award for…
3
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…
4
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.
5
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.
6
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.
7
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.
8
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…
9
The Midnight Patrol (1933)
★ 6.6/10Also comedy
Novice policemen Stan and Ollie bungle a burglary investigation.
10
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.
11
Welcome to Collinwood (2002)
★ 6.1/10Also comedy
Five hapless inner-city low-lifes attempt to burgle a pawnbroker's safe, but end up being plagued by bad luck.
12
The Big Brawl (1980)
★ 5.9/10Also comedy
A young Asian American martial artist is forced to participate in a brutal formal street-fight competition.
13
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.
14
The Stöned Age (1994)
★ 6.1/10Also comedy
Determined to avoid another night of driving aimlessly around Torrance in the Blue Torpedo, Joe and Hubbs set out on a quest for fine chicks. Their paths soon cross with Tack, from whom they learn about a pair of…
15
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.
16
Amy Schumer: Mostly Sex Stuff (2012)
★ 5.9/10Also comedy
A ratings hit! Amy Schumer debuts her one-hour special in front of a live audience at the Historic Fillmore Theatre in San Francisco. Nothing is off limits as Schumer airs every hilarious, messed up detail of her…
17
Solid Serenade (1946)
★ 7.5/10Also 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.
18
Beau Hunks (1931)
★ 6.8/10Also comedy
Stan and Ollie join the French Foreign Legion after Ollie's sweetheart rejects him.
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
Mike's New Car (2002)
★ 6.9/10Also comedy
Mike discovers that being the top-ranking laugh collector at Monsters, Inc. has its benefits – in particular, earning enough money to buy a six-wheel-drive car that's loaded with gadgets. That new-car smell doesn't…