Dynamic Watchlist Hub: May 09, 2026

10 Best Movies Like Chasing Robert

If you loved Chasing Robert, 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 Chasing Robert.

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#1
Easy Money

Easy Money

1983★ 6.0

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

To inherit his mother-in-law's colossal fortune, a hard living gambling addict must change his unhealthy ways before it gets the best of him....

#2
Dirty Work

Dirty Work

1998★ 6.2

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

Unemployed and recently dumped, Mitch and his buddy Sam start a revenge-for-hire business to raise the $50,000 that Sam's father needs to get a heart transplant....

#3
Killing Them Softly

Killing Them Softly

2012★ 6.0

Why watch this? A perfect follow-up to Chasing Robert for fans of Crime. It captures a similar compelling atmosphere.

Jackie Cogan is an enforcer hired to restore order after three dumb guys rob a Mob protected card game, causing the local criminal economy to collapse....

#4
Let It Ride

Let It Ride

1989★ 6.4

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

An average kind of guy who has a slight problem with gambling goes to the track, and mystically, it seems as though he can't lose, no matter how he bets; and he has an incredible d...

#5
Room Service

Room Service

1938★ 6.5

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

Broke Gordon Miller tries to land a backer for his new play while he has to deal with with the hotel manager trying to evict him and his cast....

#6
The Hangover Part III

The Hangover Part III

2013★ 6.2

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

This time, there's no wedding. No bachelor party. What could go wrong, right? But when the Wolfpack hits the road, all bets are off....

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