Dynamic Watchlist Hub: Apr 13, 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.

🏆

Expert Review & Ratings

See our full critical analysis and audience score for Sweepstake Annie.

View Review →
Advertisement
#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
In the Soup

In the Soup

1992★ 6.6

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

An aspiring young filmmaker gets involved with an eccentric gangster for the financing of his first film....

#3
Jackpot!

Jackpot!

2024★ 6.4

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

In the near future, a 'Grand Lottery' has been established - the catch: kill the winner before sundown to legally claim their multi-billion dollar jackpot. When Katie Kim mistakenl...

#4
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....

#5
A Nice Girl Like You

A Nice Girl Like You

2020★ 5.8

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

Lucy Neal is thrown for a loop when she is accused of being too inhibited by her ex-boyfriend. In an effort to prove him wrong, Lucy creates a rather wild to-do list that sends her...

#6
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....

Advertisement