Dynamic Watchlist Hub: May 16, 2026

10 Best Movies Like The lady from Chicago

If you loved The lady from Chicago, 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 The lady from Chicago.

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#1
Held Up

Held Up

1999★ 5.8

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

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...

#2
Pretty Persuasion

Pretty Persuasion

2005★ 5.8

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

A 15-year-old girl incites chaos among her friends and a media frenzy when she accuses her drama teacher of sexual harassment....

#3
Taylor Tomlinson: Look at You

Taylor Tomlinson: Look at You

2022★ 7.2

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

Breakups. Therapy. Bangs. Taylor's gone through some stuff since her quarter-life crisis, and she spins her mental health journey into insightful comedy....

#4
Mr. Bones

Mr. Bones

2001★ 6.0

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

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....

#5
Ricky Gervais Live 2: Politics

Ricky Gervais Live 2: Politics

2004★ 6.9

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

A year after Animals, Ricky Gervais comes back with his second stand up comedy tour: Politics....

#6
Louis C.K.: Hilarious

Louis C.K.: Hilarious

2010★ 7.8

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

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...

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