Movies Like Chicago Digest

If you liked Chicago Digest (1951), a comedy and western movie directed by Paul Paviot, 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
Go West (1940)
★ 6.6/10Also comedy and western
A con man heading west to search for gold teams up with a pair of scheming brothers along the way. The trio soon find themselves in the middle of a feud between two rival families and two underhanded land developers.
2
Aziz Ansari: Dangerously Delicious (2012)
★ 6.8/10Also comedy
Aziz Ansari channels his crude side taking on topics like watching porn and the struggles of dating in New York City.
3
Support Your Local Gunfighter (1971)
★ 6.6/10Also comedy and western
A con artist arrives in a mining town controlled by two competing companies. Both companies think he's a famous gunfighter and try to hire him to drive the other out of town.
4
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.
5
The Cheap Detective (1978)
★ 6.4/10Also comedy
A spoof of the entire 1940s detective genre. San Francisco private detective, Lou Pekinpaugh is accused of murdering his partner at the instigation of his mistress—his partner's wife.
6
Chris D'Elia: Man on Fire (2017)
★ 6.2/10Also comedy
Unbridled comic Chris D'Elia reconsiders his approach to major life events like marriage, not having kids and buying pants for your friends.
7
Demetri Martin: The Overthinker (2018)
★ 6.8/10Also comedy
With his signature one-liners and drawings, Demetri Martin muses on doughnut holes, dogs, sports bars, the alphabet's most aggressive letters and more.
8
Dave Chappelle: Sticks & Stones (2019)
★ 7.5/10Also comedy
Dave Chappelle takes on gun culture, the opioid crisis and the tidal wave of celebrity scandals in this defiant stand-up special.
9
Aziz Ansari: Intimate Moments for a Sensual Evening (2010)
★ 6.8/10Also comedy
Aziz Ansari presents his highly anticipated debut hour long stand-up special. The critically acclaimed stand-up and actor (Parks and Recreation, Funny People) discusses topics ranging from sheets with fraudulent thread…
10
Go West (1925)
★ 6.9/10Also comedy and western
With little luck at keeping a job in the city a New Yorker tries work in the country and eventually finds his way leading a herd of cattle to the West Coast.
11
Way Out West (1937)
★ 7.1/10Also comedy and western
Stan and Ollie try to deliver the deed to a valuable gold mine to the daughter of a dead prospector. Unfortunately, the daughter's evil guardian is determined to have the gold mine for himself and his saloon-singer wife.
12
Employee of the Month (2022)
★ 6/10Also comedy
Vincent, a civil servant, has always enjoyed the benefits of his family's status. When the government votes on a massive savings plan, Vincent is pushed out. When he is transferred to the North Pole, he meets Eva and…
13
Eddie Murphy Raw (1987)
★ 7.2/10Also comedy
Eddie Murphy delights, shocks and entertains with dead-on celebrity impersonations, observations on '80s love, sex and marriage, a remembrance of Mom's hamburgers and much more.
14
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…
15
Hard to Die (1990)
★ 6/10Also comedy
While doing the inventory for a lingerie outlet in a high rise office building, five attractive women are terrorized by a series of bizarre killings. They suspect that the strange janitor, who witnessed another series…
16
The Tramp (1915)
★ 6.5/10Also comedy
The Little Fellow finds the girl of his dreams and work on a family farm. He helps defend the farm against criminals, and all seems well, until he discovers the girl of his dreams already has someone in her life…
17
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.
18
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…
19
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…
20
How to Irritate People (1969)
★ 6.6/10Also comedy
A pre-Monty Python mockumentary, written by and presented by John Cleese, that provides tips on learning how to irritate people.