Dynamic Watchlist Hub: Jan 19, 2026

10 Best Movies Like Pee-wee's Big Holiday

If you loved Pee-wee's Big Holiday, 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 Pee-wee's Big Holiday.

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#1
Pottersville

Pottersville

2017★ 4.9

Why watch this? A perfect follow-up to Pee-wee's Big Holiday for fans of Comedy. It captures a similar light-hearted atmosphere.

Maynard, a beloved local businessman is mistaken for the legendary Bigfoot during an inebriated romp through town in a makeshift gorilla costume. The sightings set off an internati...

#2
Peter Pan Live!

Peter Pan Live!

2014★ 5.1

Why watch this? A perfect follow-up to Pee-wee's Big Holiday for fans of Adventure & Family. It captures a similar compelling atmosphere.

Following in the footsteps of the phenomenally successful The Sound of Music LIVE! - which drew over 18 million viewers - comes this musical masterpiece that tells the beloved stor...

#3
Big Top Pee-wee

Big Top Pee-wee

1988★ 4.9

Why watch this? A perfect follow-up to Pee-wee's Big Holiday for fans of Comedy & Family. It captures a similar light-hearted atmosphere.

Paul Reubens stars as Pee-wee Herman in his second full-length film about a farmer who joins the circus after a storm drops a big tent in his front yard. Pee-wee, along with an out...

#4
The Pee-wee Herman Show

The Pee-wee Herman Show

1981★ 7.2

Why watch this? A perfect follow-up to Pee-wee's Big Holiday for fans of Comedy. It captures a similar light-hearted atmosphere.

An adult-oriented version of what would eventually become an award-winning children's classic. This version of the show features Pee-wee's playhouse and many of the characters of t...

#5
Every Christmas Has a Story

Every Christmas Has a Story

2016★ 5.2

Why watch this? A perfect follow-up to Pee-wee's Big Holiday for fans of Comedy. It captures a similar light-hearted atmosphere.

A TV personality has an on-air snafu and admits she hates Christmas. Following the debacle, she is invited to the Most Christmas-y town in America to try and repair her image. Forc...

#6
Live in Front of a Studio Audience: "All in the Family" and "Good Times"

Live in Front of a Studio Audience: "All in the Family" and "Good Times"

2019★ 6.1

Why watch this? A perfect follow-up to Pee-wee's Big Holiday for fans of Comedy & Family. It captures a similar light-hearted atmosphere.

Live performances of classic holiday-themed episodes from Norman Lear's hit shows "All in the Family" and "Good Times."...