Movies like The lady from Chicago (1931)
The best movies like The lady from Chicago (1931) are Held Up (1999), Shane Gillis: Beautiful Dogs (2023) and Mr. Bones (2001). If The lady from Chicago hooked you with its comedy, these 20 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedLouis C.K.: Hilarious (2010)7.8/10 from 321 votes
- NewestDriver's Ed (2026)Released 2026
Held Up (1999)
What should have been a romantic getaway turns into one hilarious debacle after another when Michael's woman dumps him in the desert where he gets carjacked by a teenager and he is taken hostage in a stickup at the local Sip and Zip.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisShane Gillis: Beautiful Dogs (2023)
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.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisMr. Bones (2001)
A medicine man is sent looking for the son of his tribal king, and brings back an American golfer and a host of goons intent on keeping him in the golf tournament.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisLouis C.K.: Hilarious (2010)
In this unique and dynamic live concert experience, Louis C.K.'s exploration of life after 40 destroys politically correct images of modern life with thoughts we have all had...but would rarely admit to.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisJerry Seinfeld: 23 Hours to Kill (2020)
Jerry Seinfeld takes the stage in New York and tackles talking vs. texting, bad buffets vs. so-called "great" restaurants and the magic of Pop Tarts.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisTaylor Tomlinson: Have It All (2024)
Can Taylor Tomlinson have it all? From dating woes to dream jobs to inventive dirty talk, she shares life's ups and downs in this stand-up comedy special.
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 thisPretty Persuasion (2005)
A 15-year-old girl incites chaos among her friends and a media frenzy when she accuses her drama teacher of sexual harassment.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisTaylor Tomlinson: Look at You (2022)
Breakups. Therapy. Bangs. Taylor's gone through some stuff since her quarter-life crisis, and she spins her mental health journey into insightful comedy.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisJerry Seinfeld: I'm Telling You for the Last Time (1998)
Taped for HBO in August 1998, on the final date of Jerry Seinfeld's tour appearances at New York City's Broadhurst Theater, I'm Telling You for the Last Time presents the standup comedian's so-called "final" standup, or at least his final tour with the standup material that made him famous.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisDriver's Ed (2026)
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.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisClear History (2013)
Nathan Flomm, in order to avoid the humiliation of having missed out on a hugely successful business, assumes a new identity on Martha's Vineyard. He plots revenge when his former business partner moves to the same town.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisDave Chappelle: Killin' Them Softly (2000)
Dave Chappelle returns for a stand-up to D.C. and riffs on politics, police, race relations, drugs, Sesame Street and more.
Why it matches: Recommended by TMDB viewers · both comedy
Absolute CinemaMovies 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 thisRicky Gervais: Armageddon (2023)
Ricky Gervais dishes out controversial takes on political correctness and oversensitivity in a taboo-busting comedy special about the end of humanity.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisAdventures in Public School (2018)
A socially-awkward, home-schooled kid forces his way into public school against his suffocating, but loving, mother's wishes.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisRicky Gervais: Humanity (2018)
In his first special in seven years, Ricky Gervais slings his trademark snark at celebrity, mortality and a society that takes everything personally.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisMike Birbiglia: Thank God for Jokes (2017)
Mike Birbiglia declares that a joke should never end with "I’m joking." In his all-new comedy, Birbiglia tiptoes hilariously through the minefield that is modern-day joke-telling. Join Mike as he learns that the same jokes that elicit laughter have the power to produce tears, rage, and a whole lot of getting yelled at. Ultimately it's a show that asks, “How far should we go for the laugh?”
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisGabriel Iglesias: Hot and Fluffy (2007)
Gabriel Iglesias is one of the fastest-rising comics today! With his unique brand of humor, lovable stage presence and wide range of voices and impressions, it's no wonder that he already has a huge fan following. Now you can see Comedy Central's "Comic of the Year" in his sold-out performance at the historic Fox Theatre in Bakersfield, California!
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisLaRoy, Texas (2024)
Broke and depressed, Ray is mistaken for a dangerous hitman and given an envelope of cash. Along with his P.I. friend Skip, he must escape the actual hitman to make it out of LaRoy alive.
Why it matches: Recommended by TMDB viewers · both comedy
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Frequently asked questions
What are the best movies like The lady from Chicago?
The closest matches to The lady from Chicago are Held Up (1999), Shane Gillis: Beautiful Dogs (2023) and Mr. Bones (2001). Below are 17 more, each with the reason it matches.
What should I watch after The lady from Chicago?
Start with Held Up (1999), the closest match to The lady from Chicago.
What is the highest-rated movie like The lady from Chicago?
Louis C.K.: Hilarious (2010), rated 7.8/10 by 321 TMDB users.
What is the newest movie like The lady from Chicago?
Driver's Ed (2026) is the most recent release on this list.
Are there English movies like The lady from Chicago?
Yes: Held Up (1999), Shane Gillis: Beautiful Dogs (2023) and Mr. Bones (2001).
How are movies similar to The lady from Chicago chosen?
First come films that Trakt’s viewers watch alongside The lady from Chicago, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.