Willie Nelson And Bob Dylan Deliver A Mesmerizing Rendition Of “You Win Again”

In 2004, Willie Nelson and Bob Dylan collaborated on a rendition of Hank Williams’ classic song “You Win Again.” This performance was part of Nelson’s live album and DVD, “Outlaws & Angels,” recorded on May 5, 2004, at The Wiltern Theatre in Los Angeles. The event featured various artists, but the duet between Nelson and Dylan stood out, blending their distinctive styles to honor Williams’ legacy.

Their collaboration on “You Win Again” has been praised for its heartfelt delivery and the seamless fusion of Nelson’s smooth vocals with Dylan’s unique voice. This performance is available on the “Outlaws & Angels” DVD, allowing fans to experience this memorable musical moment. You can watch the performance here:

Now, Bob Dylan and Willie Nelson are joining forces once again for the highly anticipated Outlaw Music Festival tour. Kicking off on May 13, 2025, in Phoenix, the tour will span 35 cities before wrapping up on September 19 in East Troy, Wisconsin.

Fans can expect a rotating lineup of talented artists throughout the tour. Some of the big names set to take the stage include Sheryl Crow, Wilco, Billy Strings, Nathaniel Rateliff & The Night Sweats, The Avett Brothers, Lake Street Dive, Waxahatchee, Lucinda Williams, and Bruce Hornsby & The Noisemakers. With such a diverse lineup, each show promises to bring something special to the stage.

Rolling Stone revealed, “What an amazing lineup to celebrate the 10th anniversary of the Outlaw Music Festival Tour.” He continued, “I can’t wait to join friends and family in bringing this celebration to the fans we love.”