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Willie Nelson's big Frank Sinatra regret

It’s a well-known fact that outlaw country hero Willie Nelson is a “huge” fan of the iconic crooner Frank Sinatra. Famously, the duo collaborated for a string of shows in Las Vegas. Showing just how far Nelson had risen since his humble Texas beginnings, Sinatra even opened for him in 1984 at the Golden Nugget Casino.

However, Nelson has admitted that he holds one regret from his friendship with the ‘My Way’ legend. 

The friendship of Sinatra and Nelson first blossomed out of mutual love for the other’s craft. “Practically everything he’s recorded, I’ve loved it. I’m a huge Sinatra fan,” Nelson told Today. 

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When you stop to think about it, there are many parallels in the vocal delivery of both figures. Nelson’s vocal delivery contains the dulcet, powerful hues of Sinatra, which undoubtedly came from him repeatedly trying to emulate his idol as a young upstart. 

Nelson has even covered Sinatra songs over the past, and of singing his hero’s songs: “I don’t think anybody expected me to sound like Frank, even though I wish I could. I don’t have that good of a voice.”

Sinatra was reciprocal in his love for Nelson. Per an account in AARP, he was known to label Nelson, his favourite musician after hearing his critically acclaimed 1978 album, Stardust, which features moments such as ‘Blue Skies’ and ‘Moonlight in Vermont’. During that same interview with The View, Nelson happily said that receiving praise from Sinatra is “as good as it gets”. 

However, Nelson doesn’t remember all of his time with Sinatra so happily. His regret came after one of the life-affirming shows in Las Vegas, where Nelson was forced to forgo an opportunity that many have dreamed of. 

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

It’s unclear what pressing issue was pulling Nelson to Los Angeles, as anyone in their right mind would have dropped what they were doing in an instant, and headed straight over to Sinatra’s place. To have been in the company of Sinatra was one thing, but to be invited to his place to hang out is a different matter entirely. 

We can only presume that whatever Nelson had to do was serious. To kick back with Sinatra and be regaled of the swinging days of the Rat Pack would have been incredible. There’s no wonder that Nelson kicks himself. 

Listen to Willie Nelson’s cover of Frank Sinatra’s ‘My Way’ below.