Jerry Seinfeld’s groundbreaking web series Comedians in Cars Getting Coffee features an episode with Jay Leno talking about the time he was “asked” to perform for mobsters by Frank Sinatra.
To summarize: Sinatra and his agent once asked Leno to perform at a Chicago benefit, and Leno politely declined, since he was booked in Pittsburgh at that time. Two hours later, he told Seinfeld, he received this call: “‘Hey, we called the Holiday House; they don’t need ya.’ What? ‘They don’t need ya.’ But I’m booked there. ‘Well, they don’t need ya. Wanna go to Chicago?’”
Somehow, the story ends with Leno on a golf course with a famous mob boss threatening a priest, and topless 50-year-old hookers.
Mediaite has the video