Pee-wee's Big Holiday is a 2016 American adventure comedy film directed by John Lee and written by Paul Reubens and Paul Rust. The film stars Reubens as Pee-wee Herman and Joe Manganiello as himself. It is the second standalone sequel to Pee-wee's Big Adventure (1985), following Big Top Pee-wee (1988), and Reubens' final feature film role before his death in 2023.

The film underwent a prolonged period of development and was born out of two different completed scripts Reubens had mentioned as early as 2004: a black comedy called The Pee-wee Herman Story, where Herman becomes a singing star and moves to Hollywood; and a screen adaptation of his television series Pee-wee's Playhouse. Pee-wee's Big Adventure director Tim Burton was approached to direct but declined to participate.

In June 2010, it was announced that Reubens was now working with Judd Apatow on a new film, from a screenplay written by Reubens and Paul Rust. Pee-wee's Big Holiday began filming on March 16, 2015, and Reubens stated that the project had been greatly delayed due to script leaks. The film premiered at South by Southwest on March 17, 2016, and was released on Netflix the following day.