For the past sixteen years, Eric Clapton has funded his Crossroads drug and alcohol rehabilitation clinic in Antigua with a series of all-star benefit concerts. The shows have mostly spotlighted guitar icons like Jeff Beck, Buddy Guy, Carlos Santana and Bo Diddley, but the inaugural show at Madison Square Garden in the summer of 1999 had a very different sort of lineup with Bob Dylan, Sheryl Crow and Mary J. Blige joining Clapton throughout a very long and inspiring evening.
The 32-song show was packed with too many great moments to mention, but the highlight came near the end when Bob Dylan took the stage. It was a tough slot since Clapton had just busted out an electric “Layla,” but Dylan – then at the pinnacle of his post-Time Out Of Mind comeback – was ready for the challenge. They kicked off their set of duets with “Don’t Think Twice, It’s All Right,” which Clapton played on that same stage seven years earlier at the Bob Dylan 30th Anniversary Celebration. Check out video of it above.
They followed it up with a bluesy “It Takes a Lot to Laugh, It Takes a Train to Cry,” a tender “Born in Time” (which Clapton covered on his 1998 LP Pilgrim), a haunting “It’s Not Dark Yet,” a rollicking “Leopard Skin Pillbox Hat” and wrapped up with “Crossroads,” showcasing their shared love of Robert Johnson. At the end of the night, Dylan joined all the evening’s guest for a cover of Jimmy Reed’s “Bright Lights, Big City.”
The only bummer of the evening was that announced guest D’Angelo didn’t show up, though seven years later the soul singer wound up at the actual Crossroads Center where he successfully kicked his alcohol addiction. Clapton played a major role in convincing him to check into the facility.