The 5 Best ‘SNL’ Frank Sinatra Bits

5 Sinatra Duets

Late-career Sinatra was introduced to a new generation via a series of duets with contemporary artists of the day. Phil Hartman does the honors here, ripping it up with Bono, Kenny G and Meat Loaf.

4 Frank Sinatra Dating Advice

Woody Allen and Soon-Yi (really, Rob Schneider?) run into Mia Farrow outside a movie theater. They’re interrupted by Hartman’s Sinatra, who gives Allen some love advice that the neurotic comic should have considered in real life. 

3 I Did It In My Style

It’s Fred Armisen as a Danish song-and-dance man taking on the role of a lifetime — Sinatra. Essential if you’ve ever wanted to see Sinatra through the eyes of Denmark.

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2 Ebony and Ivory

How into his Sinatra impression was Joe Piscopo? In the script for this sketch, “Frank was supposed to be waiting for Stevie Wonder to show up at the recording studio and Joe said, ‘Frank wouldn’t wait for Stevie. Stevie would have to wait for Frank,’” recalls SNL writer Bob Tischler in SNL oral history Live From New York. “It was sick.”

“Joe needed to think he was Frank Sinatra,” remembers SNL scribe Andrew Smith. “And we wanted to write a sketch called ‘Frank Wouldn’t Do that,’ because we’d pitch a sketch, and Joe would say, ‘No, no, Frank wouldn’t do that.’ I once wrote a sketch — ‘The Gay Frank Sinatra Club.’ And ‘No, not that, Frank wouldn’t do that.’ So he really got a little squirrelly about this whole Frank Sinatra thing. Joe saw his Frank thing not in comedy terms but as a tribute.”

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1 The Sinatra Group

“Phil (Hartman) was just a runaway freight train in (this) scene,” SNL writer Robert Smigel told me. “He just had so much charisma and confidence that it was a classic. It’s interesting — the Sinatra family did not like it. I remember that very well. Joe Piscopo had done Sinatra many times. It wasn’t dark at all. He didn’t really touch on the tough guy, kind of reactionary guy who in concert would say things like, ‘If Sinead O'Connor wasn’t a chick, I’d kick her ass.’”