How Pee Wee Herman Inspired One of Tupac’s Biggest Hits

On Sunday (July 30), beloved actor Paul Reubens passed away after a years-long bout with cancer. Best known for his comedic role as Pee-Wee Herman, Reubens’s lovable 1980s character inspired many creatives in the years following, whether it be fellow actors, writers, or even musicians.

One example of this was, surprisingly, Tupac, who rose to fame about a decade after Reubens did. When the iconic rapper put out his fourth studio album, All Eyez on Me, his last full-length release before his tragic death in September 1996, he included “Ambitionz az a Ridah” as the LP’s intro. Produced by the esteemed Daz Dillinger, one half of Tha Dogg Pound duo with Kurupt, cousin of Snoop Dogg, and frequent collaborator with West Coast emcees like Pac and Dr. Dre, “Ambitionz az a Ridah” was made just after Tupac was released from jail in 1995, as the song’s engineer Dave Aron noted in a 2005 interview with XXL.

“That’s the first song I ever did with Tupac,” Aron said. “The day he got out of jail, he didn’t go to the clubs. He didn’t go try to meet women. He went straight to the studio like he was on a mission, and he recorded ‘Ambitionz Az A Ridah’ and ‘I Ain’t Mad At Cha.’… He was ready to go. He was very hyped, very focused, a lot of energy—mad energy. And you could tell he was really on a mission. He really had a real vision of what was going on, and he wanted to get a lot done in that short amount of time.”

The instrumental made by Dillinger for “Ambitionz az a Ridah” samples 1980s rapper Joeski Love’s tribute to Pee-Wee Herman, titled “Pee-Wee’s Dance,” which also interpolates the classic 1958 song “Tequila” by Los Angeles band The Champs, which Pee-Wee famously danced to in a scene from his show. Dillinger discussed the idea for this in the same XXL interview.

“The idea came from me sampling Pee Wee Herman,” Dillinger told XXL. “So if you listen to Pee Wee Herman [the Champs’ “Tequila”], I just put the gangsta twist on it. I gave it to ‘Pac. Came back to the studio, and it was done.”

“Ambitionz az a Ridah” would go on to become one of the most adored songs in Pac’s catalog, and aided its accompanying album in being certified diamond in 2014.

Photo by Bobby Bank/GC Images