Willie Nelson Shares One Thing He Regrets From Frank Sinatra Friendship

Unsurprisingly, Willie Nelson has a lot of famous friends. However, his relationship with Frank Sinatra is perhaps the most unexpected. Although they came from very different words — and very different music styles — the musicians had a mutual respect for each other that translated into both friendship and collaborations over the years.

As Rolling Stone reported, Sinatra once deemed Nelson his favorite singer, and the country music star shared those feelings, writing in his memoir “Sinatra’s my favorite singer.” Of course, even great friendships aren’t perfect, and Nelson has shared one thing that he regrets from his decades-long relationship with the “My Way” singer: he passed up a chance to hang out with him after a show.

Nelson & Sinatra Played Vegas Shows Together in the ’80s

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As Rolling Stone shared, the two superstars collaborated many times over the years, including when they played a show together in Las Vegas. In 1984, Sinatra opened for Nelson at Golden Nugget, although the partnership ended up only lasting one performance. Some believed Sinatra didn’t like being an opening act, but Nelson set the record straight. “Like me, Frank wasn’t hung up on being the headliner. He was the consummate pro.”

Although this event gave the two a chance to get better acquainted, it may also have been the time when Nelson’s biggest regret about their friendship happened. As Taste of Country shared, the country singer once said that when they played a show together, possibly in Las Vegas, Sinatra asked him to hang out after. “He asked me to hang out with him awhile that night and I couldn’t. I had some place to go and get on the bus,” Nelson said. “But that was one of my biggest regrets, that I didn’t get to hang out with Frank.”

The Singer Dedicated an Album to His Late Friend

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Nelson has frequently shared his adoration for Sinatra, but he took that one step further in 2018 when he released “My Way,” a tribute album dedicated to his late friend. The album includes some true Sinatra classics, such as the eponymous hit and “Fly Me To The Moon.”

As the singer told AARP, he learned some valuable lessons from Ol’ Blue Eyes. “I learned a lot about phrasing listening to Frank,” he explained. “He didn’t worry about behind the beat or in front of the beat, or whatever — he could sing it either way, and that’s the feel you have to have.” Few people have the chance to befriend a living legend like Nelson did, and the country crooner has now become a legend himself.