From Las Vegas Shows to NASA PSAs: The Unlikely Friendship of Willie Nelson and Frank Sinatra and Nelson’s Biggest Regret When it Came to Ol’ Blue Eyes

By the early 1980s, Frank Sinatra and Willie Nelson formed an unlikely friendship. The two even did a series of NASA space research public service announcements, and Nelson later covered a collection of Sinatra’s classics on his 2018 album My Way. The album was released 20 years after Sinatra’s death and won the Grammy for Best Traditional Pop Vocal Album.

The two crooners first connected after playing a string of shows in Las Vegas in the early ’80s. Sinatra even opened for Nelson—who was already riding on his 1982 classic “Always on My Mind” and his ’84 hit duet with Julio Iglesias “To All the Girls I’ve Loved Before”—during a 1984 show at the Golden Nugget Casino in Vegas.

Both artists respected one another and became friends over time. Nelson always had a fondness for the standards and even covered them on his 1978 album Stardust, which features renditions of songs by Irving Berlin, Duke Ellington, Kurt Weill, George and Ira Gershwin, Hoagy Carmichael, and more.

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“Everybody’s gotta do what they feel,” said Nelson in his 2021 memoir Letters to America. “I don’t try to force my music on anybody. I grew up listening to all kinds of music. Doing the ‘Stardust’ album was easy because I knew the songs. Doing the Sinatra album was simple because I knew all his songs. I knew all of the ‘Stardust’ songs as well as I knew my own songs because I did them every night.”

Nelson added, “There’s a reason they’re called standards. There’s a melody and lyric there that millions of people feel and hear.”

Despite their friendly collaborations, Nelson always regretted one thing about his time ol’ blue eyes. Sinatra once invited Nelson to hang out at his home after a show many years ago. Unfortunately, Nelson had to get back on the road and left.

“One night we played a show in Vegas, and he invited me by his place to hang out, and I couldn’t,” revealed Nelson. “I had to get on a bus and go to LA, and I always regretted that I didn’t get to hang out with Frank.”

Along with being a friend, Nelson considered Sinatra one of his “heroes” in music. “He was a great friend, but he was also my favorite singer,” said Nelson in his book. “I loved his choice of songs. I loved his lifestyle. I loved his acting. He invited me to his house, and I had to get on a bus and go somewhere else, but I always regret not being able to spend that night hanging out with Frank

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“A Foggy Day”

In 1994 Nelson duetted with Sinatra on the singer’s 59th and final album, Duets II, swapping verses on George and Ira Gershwin’s “A Foggy Day.” Originally, the Gershwins’ wrote the song, also called “A Foggy Day (in London Town),” for the 1937 film A Damsel in Distress, starring Fred Astaire. Sinatra first covered the song on his 1953 album Songs for Young Lovers before revisiting it with Nelson.

“Since Sinatra has always been one of my heroes,” said Nelson at the time, “doing a song with him is the ultimate.”

Sinatra won a Grammy Award for Best Traditional Pop Vocal Performance for his duets album. Nelson later recorded “A Foggy Day” on his Sinatra tribute My Way. Both also recrorded a duet of “My Way” that wasn’t releasd on the album.

Photo: Willie Nelson (l), Photo by Michael Ochs Archives/Getty Images); Frank Sinatra, Photo by Daniel Rosenblum/Keystone/Getty Images

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