Toby Keith says he knew immediately after John Prine died that his next album would include a tribute. Picking the right song for that tribute wasn't quite as easy.

Prine died on April 7, 2020 after contracting COVID-19. He was 73 years old and regarded as one of the greatest living songwriters. Keith says he discovered Prine's catalog about 20 years earlier, and he met him several times.

"I was a huge fan," Keith shares, talking to Taste of Country Nights' host Evan Paul. "He put — I mean my whole career, I've written that big catalog. Say I had three gears in my transmission. He put a fourth gear in the box."

Among Prine's famous early works were "Illegal Smile," "Paradise" and "Angel From Montgomery." "You Never Even Called Me by My Name" came later, and he remained dedicated to the craft until his death. In 2018 he released what would be his final album, Tree of Forgiveness. It would earn a Grammy nomination.

For Peso in My Pocket, Keith chose Prine's "Take a Look at My Heart," originally recorded on The Missing Years album (1991) with Bruce Springsteen. He says he didn't want to choose from the same group of well-known songs others would inevitably choose from. In fact, he'd never even heard the song until recently, when while running, it came up on a streaming playlist.

John Mellencamp helped Prine write "Take a Look at My Heart," something Keith says he clearly heard once he began exploring the lyrics and chord changes in the studio. Choosing one of Prine's hits would have been the safer play, but that would have rubbed against everything the 60-year-old learned from a man he considers a songwriting hero.

"He taught me to be fearless," Keith says, "And not care for the sake of the song by commercializing anything, or having a thought in your head that they won’t play it if I do this."

"It was a big loss," he says, slowing down some to reflect on Prine's death. "I just wanted to pay tribute to the guy."

Peso in My Pocket is Keith's first studio album in six years. It was released last Friday (Oct. 15) and includes his single "Old School."

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