He was a friend and confidante to presidents, congressmen, and first ladies. He was honored with the Presidential Medal of Freedom at a White House ceremony in 1985. A dozen years later, Congress followed with its highest civilian award, the Congressional Gold Medal. He performed at several inaugural balls, and had numerous tributes entered into the Congressional Record.
So it should come as no surprise that in 2008, on the tenth anniversary of his passing, Frank Sinatra received another of the top honors the United States can bestow on one of its citizens—a postage stamp bearing his likeness.
The Sinatra stamp, good for the new first class postage rate of 42 cents, was announced in early December, 2007, and unveiled at a Beverly Hills ceremony on what would have been Sinatra’s 92nd birthday on December 12. In making the announcement, Postmaster General John Potter cited Sinatra’s “legendary gift for transforming popular song into art.”
The stamp, which pictures an elegant Sinatra in fedora and gray suit, won raves from the Sinatra family. “We were thrilled immediately,” Nancy Sinatra has said. “It was absolutely beautiful.”
For Richard Sheaff, an Arizona-based designer who served as art director of the Sinatra stamp for the U.S. Postal Service, the experience with the Sinatra family was a welcome change from the troubles he sometimes endures when he designs stamps that picture well-known entertainers.
“In this case, the family was very easy to work with, which is often not the case,” says Sheaff, who has designed or art-directed more than 400 stamps over the past 25 years, including those depicting such pop-culture icons as Alfred Hitchcock, Andy Warhol, singers Paul Robeson and Roy Acuff, and, also this year, actress Bette Davis.
“With lots of famous families,” he adds, “you show them the design and they immediately say, ‘Oh no, that doesn’t look like him at all.’”
He laughs. “Hollywood families are often dysfunctional, and in some cases the process can go on for years. We’ve had instances where the rights are shared between two different families who aren’t speaking to each other. There have been times when we’ve eventually said, ‘If you don't approve this design, there won't be a stamp at all.’”
In the case of the Sinatra stamp, though, Sheaff says the family was not only relaxed and cooperative, but they provided the image that was eventually used.
“When you’re dealing with somebody like Frank Sinatra, who had such a long career, one of the difficult things is figuring out which stage of his life you want to use. There was a lot to choose from, because he was very photogenic and he took a ton of photos throughout his career.”
Initially, Sheaff says he settled on a shot from early in Sinatra’s career, in which the singer was looking directly into the camera. “And I think it was Tina Sinatra who pulled out a different shot and said, ‘What about this one?’ With all the looking we’d done, we’d never seen that shot before. But it was perfect.”

Sheaff hired artist Kazuhiko Sano to execute the design. “He’s a terrific talent, and he does people beautifully,” he says of Sano, who has done everything from book coves to movie posters to limited edition prints, and whose previous stamps include tributes to the TV series All In The Family, the racehorse Secretariat, and a style of music Sinatra wisely never attempted, disco.
“He does other things, too,” says Sheaff of Sano’s range. “But when you want something that really looks right on, almost like a photograph, he’s great.”
In designing this particular stamp, Sheaff even admits that he may have made a few points in the eyes of his aunt and uncle. “They were huge Sinatra fans,” he says. “He’s all they ever listened to, all they ever played.”
Of course, their nephew teased them about it. “I was growing up in the `60s listening to rock 'n' roll,” Sheaff concedes, “so I spent half my childhood giving them a hard time about listening to Sinatra. But as I grew older, I began to appreciate him more and more.”
And now… “Well, when the stamps came out, I sent my aunt a bunch of first-day covers,” he says. “And I’ll probably get her a copy of the new CD.” (That CD, Nothing But The Best, sports the same cover as the new stamp.)
This isn’t the first time Sinatra has been honored by the U.S. Postal Service. In 2002, four years after his death, the post office in his hometown of Hoboken, New Jersey was renamed in his honor. But the stamp—120 million of which will be produced—would have been a particular thrill to an extremely patriotic man, said the Sinatra family.
When he recorded for Columbia Records in the 1940s, Sinatra expressed his appreciation for and his vision of the United States in the song “The House I Live In (That’s America to Me).” Written by Lewis Allen (lyrics) and Earl Robinson (music), the song paints a picture of a country made great by a diverse people free to speak their minds: “The church, the school, the clubhouse, the million lights I see/ But especially the people, that’s America to me.”
Sixty-two years later, America is expressing its appreciation right back to the man who sang those words.






