Frank Stallone On Don Rickles Roasting Sly When His Career Was Going Down The Toilet

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Frank Stallone joined our Endless Hustle podcast this week to discuss a variety of things:

  • Making a name from himself outside of Sylvester Stallone’s brother
  • The inner-workings of the Rocky franchise
  • This new documentary, Stallone: Frank, That Is
  • Whether or not he took offense to Norm McDonald constantly using him as the punchline for his Weekend Update bit.

Stallone, a Grammy-winning musician, also discussed opening for Don Rickles and how a Frank Sinatra gesture bailed him out of an awful date.


“[Don] would always break my balls no matter what. But he was a very nice guy. When I was playing a gig with him and my brother and Jennifer came there. Sly’s career was kind of in the toilet. This is before Rocky Balboa and the big comeback, The Expendables. So his career wasn’t doing well.

He goes, ‘Hey Sly. How you doing?’ He puts his arm around him. He goes, ‘It’s over, kid. Don’t worry about it.’ He was very funny.”

If only we all had a friend like Frank Sinatra…

“He introduced me at the Hollywood Bowl. And so I’m there and I’m on a date and it’s just not happening, man. It’s just one of those things where you go, ‘Why did I bring this girl here?’ And I’m under the star in the Hollywood Bowl. It’s beautiful out. It’s Frank Sinatra. If you can’t get it on with that, you should kill yourself. I’m like, ‘I could have brought this other chick with me, it would have been great.’

So at the end, Rickles used to come out with two glasses of Jack Daniels for the final. And Frank salutes and [guzzles it down] and goes, ‘By the way, is Frankie Stallone out there?’ And I’m up really close. I’m like, ‘Oh my God.’ And I go, ‘Yes, I am!’ Hey I heard your new album with Billy May. It knocked my socks off, kid. Salute.

Now the girl next to me, all the sudden now I’m the best thing. So she’s on me like a cheap suit. I said, ‘Ya know what, you bum me out. Take a cab, you’re outta here.’

And those other girls came around. It was a good night.”

Check out the entire Stallone interview below:

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Matt’s love of writing was born during a sixth grade assembly when it was announced that his essay titled “Why Drugs Are Bad” had taken first prize in D.A.R.E.’s grade-wide contest. The anti-drug people gave him a $50 savings bond for his brave contribution to crime-fighting, and upon the bond’s maturity 10 years later, he used it to buy his very first bag of marijuana.