Nick looks back at the one and only time Jay Leno hosted Saturday Night Live on February 22, 1986. At the time, Leno was still a rising stand-up comedian, years away from his Tonight Show fame, with a hot reputation and a career on the rise. Despite his popularity, Leno was underused on the episode, largely because he lacked skill in sketch comedy and acting. Instead, he spent most of the show either playing a stand-up comedian or taking on quiet background roles.

In this episode, you’ll hear his monologue from that show, along with a few sketches from the notorious and troubled 11th season. Nick also shares behind-the-scenes details about Leno’s strained relationship with Lorne Michaels and SNL, a dynamic that affected both Leno’s appearances and his eventual relationship with The Tonight Show. You’ll also hear about Leno’s one other appearance on SNL in 1992, when he did a Weekend Update commentary on the L.A. Riots.

Jay Leno and SNL were never quite a great fit, and after listening, you’ll understand why. [Ep99]