Dynamic Watchlist Hub: Apr 10, 2026

10 Best Movies Like The Boss

If you loved The Boss, 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 Boss.

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#1
Casino Jack

Casino Jack

2010★ 5.8

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

Based on a true story, a hot shot Washington DC lobbyist and his protégé go down hard as their schemes to peddle influence lead to corruption and murder....

#2
Married to the Mob

Married to the Mob

1988★ 6.0

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

Angela de Marco is fed up with her gangster husband's line of work and wants no part of the crime world. When her husband is killed for having an affair with the mistress of mob bo...

#3
Veronica Mars

Veronica Mars

2014★ 6.6

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

Years after walking away from her past as a teenage private eye, Veronica Mars gets pulled back to her hometown - just in time for her high school reunion - in order to help her ol...

#4
The Stöned Age

The Stöned Age

1994★ 5.9

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

Determined to avoid another night of driving aimlessly around Torrance in the Blue Torpedo, Joe and Hubbs set out on a quest for fine chicks. Their paths soon cross with Tack, from...

#5
The Duchess and the Dirtwater Fox

The Duchess and the Dirtwater Fox

1976★ 6.1

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

A female hustler is chasing after rich men, but becomes repeatedly mixed up with a suave con man and card shark through a series of misadventures before falling in love with him....

#6
Jackass Presents: Bad Grandpa

Jackass Presents: Bad Grandpa

2013★ 6.1

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

86-year-old Irving Zisman is on a journey across America with the most unlikely companion: his 8 year-old grandson, Billy....

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