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.