WATCH: Jay Leno Recalls How Frank Sinatra Forced Him to Perform for the Mob

In the latest installment of his series Comedians in Cars Getting Coffee, Jerry Seinfeld took The Tonight Show host and his friend of 35 years Jay Leno to get his very first coffee, ever, while they both discussed the state of comedy today. But in 35 years, Leno’s seen some strange things in his career — including, he recalled, the time where Frank Sinatra somehow coerced him into performing for a Mob benefit in Chicago.

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.

You can watch the story below:

[h/t Uproxx]

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