The Meetup Between Willie Nelson and Frank Sinatra That Nelson “Always Regretted”

Willie Nelson is one of the chillest people on the planet, so it’s not exactly surprising that he had a friendly relationship with virtually every music he encountered. Just because the man made outlaw country music doesn’t mean he’s a stone-cold cowboy.

One unlikely friendship that Nelson enjoyed was with the legendary singer Frank Sinatra. The pair once collaborated for a few sets in Las Vegas decades ago. Sinatra also opened for Nelson in 1984 for his Golden Nugget Casino show.

According to Nelson, though, he does have his regrets about the friendship. Namely, he regrets not meeting up with Sinatra for some legendary hang-out time.

The Willie Nelson and Frank Sinatra Meetup That Never Was

It’s a sad tale, indeed. But it doesn’t detract from these two music icons’ friendship. Both Nelson and Sinatra were vocal fans of each other’s music, with Nelson going as far as to say that he loved “practically everything” Sinatra ever recorded. Sinatra was a big fan of the 1978 album Stardust. It makes sense why they inevitably worked together several times. Nelson has even covered a Frank Sinatra song or two, though he said he doesn’t have “as good of a voice” as Sinatra. You and me both, Willie.

Sadly, Nelson does have one regret about the friendship. According to Nelson, after one of his shows that Sinatra opened in Las Vegas, Nelson missed out on quite the opportunity.

“One night we played a show in Vegas, and he invited me by his place to hang out, and I couldn’t,” said Nelson in an interview with Today. “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.”

Nelson didn’t clarify what the important event was that he had to bail on Sinatra for, but we can only hope it was saving the world or something. Sadly, Nelson never got the chance to have a good ol’ kickback with Sinatra after that. Sinatra passed away at the age of 82 in 1998.

Still, Nelson is certainly fortunate to have gotten so much praise from Sinatra when he was alive and to even work with him. Now, Nelson himself is a certified legend that any fan would kill to hang out with or open for.

Photos by Michael Ochs Archives/Daniel Rosenblum

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