When Kenny Rogers first heard “The Gambler,” he was convinced he knew exactly who should sing it. To Rogers, the song felt tailor-made for his longtime friend Willie Nelson. So he did what musicians often do—he offered it to him. But Nelson surprised him by saying no.
The story of “The Gambler” stretches back before that moment. Songwriter Don Schlitz penned the track in 1976, and it was initially recorded by Bobby Bare in 1978. Despite its strong storytelling, Bare’s version failed to make much of an impact. Schlitz later recorded the song himself, and Johnny Cash also cut his own version, releasing it on his 1978 album Gone Girl.
That same year, Kenny Rogers took a chance on the song—and everything changed. His rendition of “The Gambler” shot to No. 1 on the country charts and crossed over to the mainstream, reaching No. 16 on the Billboard Hot 100. The song became a cultural phenomenon and earned Rogers a Grammy Award in 1980 for Best Male Country Vocal Performance. More than any other hit in his catalog, “The Gambler” became his defining song.
But it almost never happened.
After Rogers’ passing in 2020, Willie Nelson reflected on their friendship during an interview with TODAY’s Jenna Bush Hager. It was there that Nelson revealed Rogers had originally wanted him to record “The Gambler.”
“He tried to get me to record it,” Nelson recalled. “He played it for me, and I told him, ‘It’s a great song, but I don’t think I’ll do it.’”
Nelson explained his reasoning was simple—and practical. At the time, he was already performing “Red Headed Stranger” every night, a famously long song with countless verses. He didn’t want to add another lengthy narrative piece to his set, nor did he want to stop performing the song that had become central to his shows.
“So I told him I just didn’t want to do another long song,” Nelson said. “And I couldn’t quit doing ‘Red Headed Stranger.’ He said, ‘Okay, I’ll record it myself.’ And that’s what he did.”
Looking back, Nelson has no regrets. He’s been clear that the song ended up exactly where it belonged.
“That was Kenny’s song all the way,” Nelson said.
History agrees. While many artists passed through “The Gambler,” it ultimately found its home with Kenny Rogers—where it remains one of the most iconic songs in country music history.