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Willie Nelson and Frank Sinatra, By the Numbers

For example, who was arrested more often?

spinner image music and cultural icons frank sinatra and willie nelson
Frank Sinatra (left) and Willie Nelson
Michael Ochs Archives/Wally McNamee/Getty Images

Frank Sinatra and Willie Nelson, 87, might not seem like a match made in musical heaven, but their friendship goes way back. Ol’ Blue Eyes reportedly called The Red Headed Stranger his favorite singer after hearing his 1978 album Stardust, and the unlikely duo even teamed up for a series of Las Vegas concerts in the ‘80s.

Sinatra died in 1998, but Nelson's admiration has grown only stronger over the years. In 2018 he released My Way, a collection of covers that earned him the Grammy for best traditional pop vocal album, and this month sees the debut of his much-anticipated follow-up That's Life — with 11 newly recorded Sinatra tunes. One was a swingin’ Rat Pack member, the other a honey-voiced outlaw troubadour; so how do their decades-long careers stack up when examined side by side? Here, a by-the-numbers look at two of the towering giants of 20th-century popular music (plus a few choice Willie and Frank videos to enjoy).

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Year Born

Frank: 1915, in Hoboken, New Jersey

Willie: 1933, in Abbott, Texas

Years in the Military

Frank: 0. Classified 4-F (medically ineligible) by the local draft board, because his eardrum had been punctured by the doctor's forceps as he was being born.

Willie: 0.75. Enlisted in the U.S. Air Force after leaving high school in 1950; medically discharged after nine months due to a bad back caused by years of baling hay.

Year Recorded First Single

Frank: 1939, “From the Bottom of My Heart"

Willie: 1957, “No Place for Me”

Grammy Awards

Frank: Nine wins out of 31 nominations, plus three honorary awards. Sinatra also has 13 songs in the Grammy Hall of Fame.

Willie: Ten wins out of 52 nominations, plus two honorary awards. In 2018, Nelson won best traditional pop vocal album for his first Sinatra tribute album, My Way.

spinner image Frank Sinatra holds the Jean Hersholt Humanitarian Award at the Academy Awards
Frank Sinatra holds the Jean Hersholt Humanitarian Award he received at the 43rd Academy Awards.
Frank Edwards/Fotos International/Getty Images

Academy Awards

Frank: One win out of 2 nominations, plus the honorary Jean Hersholt Humanitarian Award. He won best supporting actor in 1954 for From Here to Eternity, and lost best actor in 1956 for The Man with the Golden Arm.

Willie: Zero wins out of 1 nomination. “On the Road Again” from Honeysuckle Rose was nominated in 1981 for best original song, but it lost to “Fame."


Frank: Twice in 1938, for “seduction” and “adultery."

Willie: At least four times for — you guessed it! — marijuana possession in 1974, 1994, 2006 and 2010.

Kennedy Center Honors

Frank: 1983, alongside actor James Stewart, director Elia Kazan, dancer Katherine Dunham, and composer Virgil Thompson.

Willie: 1998, alongside conductor André Previn, actress Shirley Temple Black, composer John Kander (93), lyricist Fred Ebb, and Bill Cosby (83) — whose honor was rescinded in 2018.

spinner image The Frank Sinatra star on the Hollywood Walk of Fame
One of Frank Sinatra's stars on the Hollywood Walk of Fame.
Brian Kinney/Alamy Stock Photo

Star on the Hollywood Walk of Fame

Frank: 1960. Sinatra actually received three stars on Feb. 8, 1960: one for motion picture at 1600 Vine St., one for TV at 6538 Hollywood Blvd., and one for recording at 1637 Vine St.

Willie: Amazingly, Nelson doesn't have one!

Saturday Night Live Appearances

Frank: 0. Although he never appeared on the show, Sinatra was impersonated by both Joe Piscopo, 69, and the late Phil Hartman (video above).

Willie: 3 — twice as musical guest (1977, 1993) and once as host/musical guest (1987).


Frank: 4, including Ava Gardner (1951-57) and Mia Farrow, 76 (1966-68).

Willie: 4, including his current wife, Annie D'Angelo (since 1991).


Frank: 3, including “These Boots Are Made for Walkin'” singer Nancy, 80.

Willie: 7, including singers Lukas, 32; and Paula, 51.

spinner image frank sinatra and willie nelson
M. Garrett/Michael Ochs Archives/Getty Images

Solo Studio Albums

Frank: 59, not counting live albums (14), compilation albums (19), Rat Pack albums (6), and albums he conducted (7).

Willie: 71, not counting live albums (13), compilation albums (51), collaborative albums (25), soundtrack albums (2), and video albums (41).


Frank: 297. The first to hit number 1 on the Billboard charts was “All or Nothing at All” in 1940.

Willie: 130. The first to hit the Top 10 on the U.S. Billboard Hot 100 was “Always on My Mind” in 1982.

Platinum Albums (1,000,000 Sold)

Frank: 12, including 3 Double Platinum and 1 Triple Platinum.

Willie: 20, including 4 Double Platinum, 3 Quadruple Platinum, and 1 Quintuple Platinum.

Holiday Albums

Frank: 4, including 1968's The Sinatra Family Wish You A Merry Christmas, recorded with his three children.

Willie: 2, including the 1979 classic Pretty Paper (Nelson had previously recorded the self-written title track in 1964 after Roy Orbison made it a hit).

Instagram Followers

Frank: 353,000 (@sinatra) — even though the social media platform wasn't started until 12 years after Sinatra's death.

Willie: 714,000 (@willienelsonofficial)

Nicholas DeRenzo is a contributing writer who covers entertainment and travel. Previously he was executive editor of United Airlines' Hemispheres magazine and his work has appeared in The New York Times, Condé Nast Traveler, Travel & Leisure, Sunset and New York magazine.

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