Pee-wee's Big Adventure, directed by Tim Burton, was a financial and critical success, marking a significant milestone in Reubens' film career.

Big Top Pee-wee, the sequel to Pee-wee's Big Adventure, was less successful but still contributed to the character's enduring popularity.

Pee-wee's Big Holiday, released by Netflix, was the last time Reubens portrayed Pee-wee Herman before his death in 2023.