Willie Nelson Is a Frank Sinatra Super Fan

The 10-time Grammy winner reveals that his first performance at age 5 didn’t go so well

Willie Nelson is set to pay tribute to the late crooner Frank Sinatra on his upcoming album of Sinatra covers, That’s Life, which releases on Friday (Feb. 26). The project follows Nelson's previous collection of Sinatra tunes, My Way, which released in 2018.

The 10-time Grammy winner recently spoke with Sunday Today with Willie Geist about his friendship with the legendary artist.

“Practically everything he’s recorded, I’ve loved it. I’m a huge Sinatra fan. 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,” he said with a laugh.

The two became friends and even teamed up in the 1980s for some public service announcements.

“We played some shows together,” Nelson recalls. “One night we played a show in Vegas and he invited me by his place to hang out and I couldn’t. 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, who turns 88 in April, also recalled his not-so-noteworthy first onstage performance when he was only five years old, when Nelson recited a poem he had written.

“My poem was, What are you lookin’ at me for?/I ain’t got nothin’ to say/if you don’t like the looks of me, just look the other way'. I was in a little white sailor suit, with red trim and I got nervous doing my poem. I started picking my nose,” he recalled with a laugh.

Nelson eventually got more comfortable onstage, and found his talent in music, penning classics such as Patsy Cline’s “Crazy." He has released more than 140 albums to date, including the seminal projects Stardust (1978) and Red Headed Stranger (1975).

He also confirmed he hastily wrote the road-warrior classic “On The Road Again,” which was featured in the movie Honeysuckle Rose, by scribbling the lyrics on the back of an airsickness bag.

“It was on an airplane,” Nelson recalls. “They wanted me to write a song for the movie we were doing,” he said.

“On The Road Again” would go on to earn a Grammy for Best Country Song and be covered by dozens of artists, further cementing Nelson's place as a top-tier writer and artist—though Nelson told Geist the first time he felt he’d made it as a performer came much earlier, at age 12.

"The first time I thought I had made it, I had been picking cotton and baling hay working in corn shellers up there in Abbott [Texas]. I got a job playing guitar when I was 12 years old. I made eight dollars. I said, ‘Hey man, I didn’t make this much picking cotton all week.’ So I found another way to go. That was my first paying gig.”

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