Movies Like Bill Hicks: Bill Loses it in Chicago

If you liked Bill Hicks: Bill Loses it in Chicago (1989), 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 Naked Gun 2½: The Smell of Fear (1991)
★ 6.8/10Also comedy
Bumbling lieutenant Frank Drebin is out to foil the big boys in the energy industry, who intend to suppress technology that will put them out of business.
2
The Onion Movie (2008)
★ 6.1/10Also comedy
Venerable newscaster Norm Archer reports the latest news in politics, health, culture and entertainment - such as an automotive recall of decapitation-inducing "Neckbelts" and a study finding that "depression hits…
3
In the Loop (2009)
★ 7/10Also comedy
The US President and the UK Prime Minister are planning on launching a war in the Middle East, but—behind the scenes—government officials and advisers are either promoting the war or are trying to prevent it.
4
Monty Python's The Meaning of Life (1983)
★ 7.3/10Also comedy
Life's questions are 'answered' in a series of outrageous vignettes, beginning with a staid London insurance company which transforms before our eyes into a pirate ship. Then there's the National Health doctors who try…
5
Dr. Strangelove or: How I Learned to Stop Worrying and Love the Bomb (1964)
★ 8.1/10Also comedy
After the insane General Jack D. Ripper initiates a nuclear strike on the Soviet Union, a war room full of politicians, generals and a Russian diplomat all frantically try to stop it.
6
Naked Gun 33⅓: The Final Insult (1994)
★ 6.5/10Also comedy
Frank Drebin is persuaded out of retirement to go undercover in a state prison. There he has to find out what top terrorist, Rocco, has planned for when he escapes. Adding to his problems, Frank's wife, Jane, is…
7
The Naked Gun: From the Files of Police Squad! (1988)
★ 7.3/10Also comedy
When the bumbling Lieutenant Frank Drebin investigates events following the shooting of his partner, he stumbles upon an attempt to assassinate Queen Elizabeth II.
8
Duck Soup (1933)
★ 7.3/10Also comedy
Rufus T. Firefly is named president/dictator of bankrupt Freedonia and declares war on neighboring Sylvania over the love of wealthy Mrs. Teasdale.
9
Dave Chappelle: The Unstoppable... (2025)
★ 6.7/10Also comedy
Facing a world gone sideways, comedy icon Dave Chappelle delivers bold truths and potent punchlines in this no-holds-barred special.
10
Dave Chappelle: The Dreamer (2023)
★ 6.9/10Also comedy
From his onstage tackle to the slap heard round the world, Dave Chappelle lets loose in this freewheeling and unfiltered stand-up comedy special.
11
The Dictator (2012)
★ 6.3/10Also comedy
The heroic story of a dictator who risks his life to ensure that democracy would never come to the country he so lovingly oppressed.
12
Jimmy Carr: Natural Born Killer (2024)
★ 6.4/10Also comedy
Jimmy Carr refutes the idea that you can't joke about anything these days with his edgy takes on gun control, religion, cancel culture and consent.
13
Britannia Hospital (1982)
★ 6.2/10Also comedy
Britannia Hospital, an esteemed English institution, is marking its gala anniversary with a visit by the Queen Mother herself. But when investigative reporter Mick Travis arrives to cover the celebration, he finds the…
14
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…
15
Oh! What a Lovely War (1969)
★ 6.7/10Also comedy
The working-class Smiths change their initially sunny views on World War I after the five boys of the family witness the harsh reality of trench warfare.
16
National Lampoon's Loaded Weapon 1 (1993)
★ 6.1/10Also comedy
An LA detective is murdered because she has microfilm with the recipe to make cocaine cookies. Two cops partner to find and stop the fiends before they can dope the nation by distributing their wares via the…
17
Chris Rock: Bigger & Blacker (1999)
★ 7.4/10Also comedy
Chris Rock brings his critically acclaimed brand of social commentary-themed humour to this HBO Special, extolling his razor-sharp wit and wisdom on such topics as gun control, President Clinton, homophobia, racism…
18
Amazon Women on the Moon (1987)
★ 5.9/10Also comedy
Centered on a television station which features a 1950s-style sci-fi movie interspersed with a series of wild commercials, wacky shorts and weird specials, this lampoon of contemporary life and pop culture skewers some…
19
The Bed Sitting Room (1969)
★ 5.9/10Also comedy
In the hazy aftermath of World War III, the fallout from a 'nuclear misunderstanding' is producing strange mutations amongst the survivors, and the noble Lord Fortnum finds himself transforming into a bed sitting room.
20
The Great Dictator (1940)
★ 8.3/10Also comedy
Dictator Adenoid Hynkel tries to expand his empire while a poor Jewish barber tries to avoid persecution from Hynkel's regime.