Remember When Kris Kristofferson Was in a Pee-Wee Herman Movie?

Kris Kristofferson is a circus ringleader who’s down on his luck in the 1988 film Big Top Pee-Wee.

The singer plays Mace Montana, who finds himself in a precarious situation after a storm leaves his traveling circus in ruins.

Luckily, his disheveled team has landed on a farm owned by Pee-Wee Herman, played by Paul Reubens. Herman helps his new friends put on the show of the century while also falling in love with a beautiful trapeze artist named Gina Piccolapupula.

Kristofferson is charming in his role as he leads and motivates his performers to get back on their feet.

This film was far from Kristofferson’s first acting gig: The “Loving Her Was Easier” singer’s earliest project was in 1971, with a film called The Last Movie. Among his more than 100 credits are blockbusters like Planet of the Apes, the Blade franchise, He’s Just Not That Into You and more.

Most recently, he was in the 2018 film Blaze.

Big Top Pee-Wee was the second Pee-Wee Herman film, following Pee-Wee’s Big Adventure. While the latter raked in more than $40 million when it hit theaters in 1985, Big Top did not see the same success. The third Pee-Wee movie, Pee-Wee’s Big Holiday, was distributed by Netflix in 2016.

Talks of Reubens’ most iconic character have resurfaced following his death. The comedian died on July 30, 2023 after a battle with cancer at the age of 70. Reubens elected to keep his health diagnosis private and battled the disease in silence for six years.

“Please accept my apology for not going public with what I’ve been facing the last six years,” the actor shared in a statement prior to his passing. “I have always felt a huge amount of love and respect from my friends, fans and supporters. I have loved you all so much and enjoyed making art for you.”