Dynamic Watchlist Hub: Jan 19, 2026

10 Best Movies Like The Caddy

If you loved The Caddy, 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 Caddy.

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#1
Edge of Winter

Edge of Winter

2016★ 5.9

Why watch this? A perfect follow-up to The Caddy for fans of Drama. It captures a similar emotionally gripping atmosphere.

When two brothers are stranded by a brutal winter storm with an unpredictable father they barely know, the boys begin to suspect their supposed protector may be their biggest threa...

#2
The Phantom Tollbooth

The Phantom Tollbooth

1970★ 6.8

Why watch this? A perfect follow-up to The Caddy for fans of Fantasy. It captures a similar compelling atmosphere.

The Phantom Tollbooth, based upon the children's adventure novel by Norton Juster, tells the story of a bored young boy named Milo. Unexpectedly receiving a magic tollbooth and, ha...

#3
Living It Up

Living It Up

1954★ 6.4

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

Homer Flagg (Lewis) is a railroad worker in the small town of Desert Hole, New Mexico. One day he finds an abandoned automobile at an old atomic proving ground. His doctor and best...

#4
Flags of Our Fathers

Flags of Our Fathers

2006★ 6.9

Why watch this? A perfect follow-up to The Caddy for fans of War. It captures a similar emotionally gripping atmosphere.

There were five Marines and one Navy Corpsman photographed raising the U.S. flag on Mt. Suribachi by Joe Rosenthal on February 23, 1945. This is the story of three of the six survi...

#5
Hollywood or Bust

Hollywood or Bust

1956★ 6.1

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

The last movie with Jerry Lewis and Dean Martin together, is a satire of the life in Hollywood. Steve Wiley is a deceiver who cheats Malcolm Smith when he wins a car, claiming that...

#6
The Nutty Professor

The Nutty Professor

1963★ 6.5

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

A timid, nearsighted chemistry teacher discovers a magical potion that can transform him into a suave and handsome Romeo. The Jekyll and Hyde game works well enough until the conco...