Dynamic Watchlist Hub: May 09, 2026

10 Best Movies Like Chicago Digest

If you loved Chicago Digest, we've curated the perfect watchlist for you based on shared genres, themes, and directorial style.

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Expert Review & Ratings

See our full critical analysis and audience score for Chicago Digest.

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#1
The Gunfighter

The Gunfighter

2014★ 7.1

Why watch this? A perfect follow-up to Chicago Digest for fans of Comedy & Western. It captures a similar light-hearted atmosphere.

In the tradition of classic westerns, a narrator sets up the story of a lone gunslinger who walks into a saloon. However, the people in this saloon can hear the narrator and the na...

#2
John Mulaney: The Comeback Kid

John Mulaney: The Comeback Kid

2015★ 7.7

Why watch this? A perfect follow-up to Chicago Digest for fans of Comedy. It captures a similar light-hearted atmosphere.

Armed with boyish charm and a sharp wit, the former "SNL" writer offers sly takes on marriage, his beef with babies and the time he met Bill Clinton....

#3
Anthony Jeselnik: Thoughts and Prayers

Anthony Jeselnik: Thoughts and Prayers

2015★ 7.4

Why watch this? A perfect follow-up to Chicago Digest for fans of Comedy. It captures a similar light-hearted atmosphere.

There's no subject too dark as the comedian skewers taboos and riffs on national tragedies before pulling back the curtain on his provocative style....

#4
The Cheap Detective

The Cheap Detective

1978★ 6.3

Why watch this? A perfect follow-up to Chicago Digest for fans of Comedy. It captures a similar light-hearted atmosphere.

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 wi...

#5
Go West

Go West

1940★ 6.5

Why watch this? A perfect follow-up to Chicago Digest for fans of Comedy & Western. It captures a similar light-hearted atmosphere.

Embezzler, shill, all around confidence man S. Quentin Quale is heading west to find his fortune; he meets the crafty but simple brothers Joseph and Rusty Panello in a train statio...

#6
Jim Jefferies: Freedumb

Jim Jefferies: Freedumb

2016★ 7.3

Why watch this? A perfect follow-up to Chicago Digest for fans of Comedy. It captures a similar light-hearted atmosphere.

Returning for a second Netflix comedy special, Jim Jefferies unleashes his famously ferocious black humor to a packed house in Nashville, Tennessee....

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