Drew Friedman draws Frank Sinatra

My favorite living portrait artist Drew Friedman offers his take on Frank Sinatra. The fine art prints, in an edition of just 35, are $165 each. From Drew's site:
 Drewfriedman Images 7047575999-1 This portrait of Frank Sinatra by Drew Friedman captures the Chairman of the Board during the 1950s, when his persona defined sophisticated swinging. Frank knew how to hold a note, his liquor, and a dame. In button-down mainstream America, Sinatra oozed free 'n easy; on the opposite side of the cultural divide, Ol' Blue Eyes didn't have to behave like a beatnik to convey cool....

Sinatra performed with the élan of an artist who had no serious competitors. The nonchalant gestures never undercut the passion in The Voice, and his smooth delivery always hinted at power in reserve. Ten years after Frank's passing, his recordings continue to enchant old fans and seduce new ones. A personality larger than life, a legacy bigger than death. "Whatever else has been said about me personally is unimportant," he claimed. "When I sing, I believe. I'm honest."

Frank Sinatra by Drew Friedman


  1. The blog Letters of Note had a letter today from Sinatra to Mike Royko, ripping him a new one in no uncertain terms- delightful read, as Sinatra calls him “nothing but a pimp”.

  2. I’m a huge Sinatra fan; so I’m really tempted to get one of these. But, in today’s economy, I just can’t justify making frivolous purchases, even at Christmastime. (Besides, if there are only 35 available, I’m sure they sold out pretty quick.)

  3. Why the awful expression on his face? Artistically, it’s a fine job, but as a Sinatra fan, I wouldn’t want it hanging on my wall.

  4. @sapere_aude: We’ve sold about one-third of the edition. Prints are still available at DrewFriedman.net.

    @Tim: Great archival letter. “Royko declined the challenge.” What a loser.

  5. hey Jaytkay: Sinatra worked at nightclubs and casinos which were all owned by the mob then. The Playboy club really first broke that hold (and to keep the mob away they hired black acts to play- Cosby, Gregory, etc). I read in Jerry Lewis’ book that he once saw Sinatra with a suitcase full of money that Sinatra joked was from the mob. Lewis wondered if the money was being laundered and Sinatra was running it for them. I did some research and it turns out Sinatra did run money- funds to Israel for the new state before it was recognized.

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