Dynamic Watchlist Hub: Jan 19, 2026

10 Best Movies Like The Waterboy

If you loved The Waterboy, 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 Waterboy.

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#1
Happy Gilmore

Happy Gilmore

1996★ 6.7

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

Failed hockey player-turned-golf whiz Happy Gilmore — whose unconventional approach and antics on the green courts the ire of rival Shooter McGavin — is determined to win a PGA tou...

#2
Bulletproof

Bulletproof

1996★ 5.7

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

An undercover police officer named Rock Keats befriends a drug dealer and car thief named Archie Moses in a bid to catch the villainous drug lord Frank Coltan. But the only problem...

#3
The Wedding Singer

The Wedding Singer

1998★ 6.8

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

Robbie, a local rock star turned wedding singer, is dumped on the day of his wedding. Meanwhile, waitress Julia finally sets a wedding date with her fiancée Glenn. When Julia and R...

#4
Billy Madison

Billy Madison

1995★ 6.2

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

Billy Madison is the 27 year-old son of Bryan Madison, a very rich man who has made his living in the hotel industry. Billy stands to inherit his father's empire, but only if he ca...

#5
Big Daddy

Big Daddy

1999★ 6.5

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

A lazy law school grad adopts a kid to impress his girlfriend, but everything doesn't go as planned and he becomes the unlikely foster father....

#6
Mr. Deeds

Mr. Deeds

2002★ 5.9

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

When Longfellow Deeds, a small-town pizzeria owner and poet, inherits $40 billion from his deceased uncle, he quickly begins rolling in a different kind of dough. Moving to the big...