Dynamic Watchlist Hub: May 10, 2026

10 Best Movies Like Sweepstake Annie

If you loved Sweepstake Annie, 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 Sweepstake Annie.

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#1
Taking Care of Business

Taking Care of Business

1990★ 6.3

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

An uptight advertising exec has his entire life in a filofax organizer which mistakenly ends up in the hands of a friendly convict who poses as him....

#2
Easy Money

Easy Money

1983★ 6.0

Why watch this? A perfect follow-up to Sweepstake Annie 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....

#3
29th Street

29th Street

1991★ 7.0

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

After winning $6.2 million in the 1976 New York State Lottery, he is arrested for throwing rocks at a church. He then tells his story at the police station....

#4
The Wedding Year

The Wedding Year

2019★ 6.0

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

A commitment-phobic 27-year old’s relationship is put to the test when she and her boyfriend attend 7 weddings in the same year....

#5
Ca$h

Ca$h

2010★ 5.9

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

A stroke of good luck turns lethal for Sam Phelan and his wife Leslie when they are faced with a life-changing decision that brings strange and sinister Pyke Kubic to their doorste...

#6
Eenie Meanie

Eenie Meanie

2025★ 6.3

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

A former teenage getaway driver gets dragged back into her unsavory past when a former employer offers her a chance to save the life of her chronically unreliable ex-boyfriend....

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