This week, we celebrate Willie’s 88th birthday with singer-songwriter Sheryl Crow, who discusses what may be the single best-known song that Willie ever wrote, “Crazy.” She’ll walk us through what it means to compose a pop standard, explaining the differences she hears in Patsy Cline’s original, 1961 version and the one that Willie still does nightly, but she’ll also describe what it does to her heart when she hears her 10-year-old son singing “Crazy” in the kitchen. And then she’ll get into her long friendship with Willie…and that time he tried to pass a backstage joint to her dad.

Even though singer-songwriter Rodney Crowell had already been a diehard Willie fan for 10 years when Phases and Stages came out in 1974, he says he was positively gobsmacked by the album’s lead single, “Bloody Mary Morning.” On this episode he dives deep into all that, then goes on to describe his first recording session with Willie a few years later...including the red Camaro he saw doing donuts outside the studio when he got there. And you will not guess who was driving.

Singer-songwriter Robert Earl Keen first heard “Mr. Record Man” as a pre-teen Houston kid who’d just raided his older brother’s record collection. It’s another deep cut off Willie’s 1962 debut album, and it makes Keen think of a dance floor mishap at his first Willie show, the time his car caught fire in the parking lot at Willie’s 4th of July Picnic, and that uncanny Everyman quality that is such a big part of Willie’s appeal.

Singer-songwriter Shakey Graves—who answers to Alejandro Rose-Garcia when he’s not onstage—discusses Willie’s biggest pop hit singing solo, “Always on My Mind.” It had been one of Elvis Presley’s signature songs of the '70s before Willie covered it in 1982, and Alejandro explains how Willie managed to pull off the impossible: stealing a song from Elvis. Then he describes the undying appeal of a good power ballad and that surreal time he signed Willie’s guitar.

Acclaimed singer-songwriter Rosanne Cash, a four-time Grammy winner and certified roots music royalty, examines “Night Life,” one of Willie’s first compositions to earn its way into the American musical canon. It’s a song that makes her nostalgic for the clean-cut, smooth-crooning Willie of the early ‘60s, but also brings up the effect of a Depression-era upbringing on artists like Willie and her dad, Johnny Cash. Oh, and she also breaks out her cell phone to play one of her favorite covers of “Night Life”—by none other than Aretha Franklin.

Acclaimed producer T Bone Burnett (Counting Crows’ August And Everything After; the Oh Brother, Where Art Thou? soundtrack; dozens of others) discusses one of the darkest songs Willie ever wrote: the early-60s murder ballad “I Just Can’t Let You Say Goodbye.” The song debuted on Willie’s 1966 album Live at Panther Hall in Fort Worth, Texas, and T Bone talks about being in the audience that night—because of course he was; he’s T Bone Burnett—along with what it was like to produce Willie himself (2010’s Country Music), and why he calls Willie a holy man.

Willie’s daughter Amy Nelson was just five years old when she first heard Kermit the Frog sing “Rainbow Connection” in The Muppet Movie, and she spent the next twenty years trying to talk her dad into recording it. In 2001, he finally did, with Amy—an accomplished musician in her own right—co-producing. She describes the way that session grew into a magical, extended-family affair mixing songs Willie once sang to his kids with a few of his more grown-up favorites, resulting in Rainbow Connection, a 2002 Grammy nominee for country album of the year.

Don Was, the legendary producer who recorded Bonnie Raitt’s “I Can’t Make You Love Me” and the B-52s’ “Love Shack,” and has worked with everyone from the Rolling Stones to Bob Dylan, calls Willie’s recording of “Across the Borderline” his favorite track he ever worked on. It was the title cut to the 1993 album that breathed new life into Willie’s career, and it prompts Don to discuss the fragile magic of a perfect first take, what it’s like to go out to eat with Willie and Ringo Starr, and the unusual sleeping arrangements Willie often makes when he’s out on the road.

Singer-songwriter Steve Earle was a longhaired, seventeen-year-old San Antonio kid when he first heard “Local Memory,” a deep cut off 1973’s Shotgun Willie. He calls it the song that first taught him that a country lyric could read like literature. Steve goes on to describe the very real tension that still existed between hippies and rednecks when Willie played outside Austin in the early 70’s, and Willie's wonderfully off-color nickname for him.