When Kenny Rogers first came across “The Gambler,” his instinct was immediate: the song felt like it belonged to Willie Nelson. Convinced it was a perfect fit, Rogers offered the track to his close friend. Nelson listened—and then politely passed.
The journey of “The Gambler” began years earlier. Songwriter Don Schlitz wrote it in 1976, and Bobby Bare was the first to record it in 1978. Despite its vivid storytelling, Bare’s version failed to gain traction. Schlitz later recorded the song himself, and Johnny Cash also released a rendition that same year on his album Gone Girl. Still, the song hadn’t found its moment.
That changed when Kenny Rogers recorded it in 1978. His version transformed “The Gambler” into a No. 1 country hit and a major crossover success, climbing to No. 16 on the Billboard Hot 100. The song went on to earn Rogers a Grammy Award in 1980 for Best Male Country Vocal Performance and became the defining track of his career.
But it nearly never happened.
Following Rogers’ death in 2020, Willie Nelson reflected on their friendship during an interview with TODAY’s Jenna Bush Hager. That’s when he revealed that Rogers had originally wanted him to record the song.
“He played it for me and said, ‘I think you should do it,’” Nelson recalled. “I told him, ‘It’s a great song, but I don’t think I will.’”
Nelson explained his reasoning was simple. At the time, he was performing “Red Headed Stranger” every night—a famously long, narrative-heavy song—and he didn’t want to add another lengthy piece to his set or give up the one audiences expected to hear.
“I just didn’t want to do another long song,” Nelson said. “So he said, ‘Okay, I’ll record it myself.’ And that’s exactly what he did.”
Looking back, Nelson has no regrets. He’s been clear that the song ended up exactly where it was meant to be.
“That was Kenny’s song all the way,” Nelson said.
History agrees. While several artists touched “The Gambler,” it ultimately became inseparable from Kenny Rogers—a reminder that sometimes the right song simply finds the right voice.