Indie Legend Jeff Tweedy Sings “Lou Reed Was My Babysitter” on ‘Jimmy Kimmel Live!’

Jeff Tweedy is one of the most prolific indie artists. His career began in the alt-country group Uncle Tupelo. The group was based out of Southern Illinois, just outside of St. Louis. Uncle Tupelo were pioneers of alt-country in the 1990s until their breakup in 1994. Initially, Tweedy played bass in the group, slowly moving over to guitar and co-lead vocal duties. He began contributing equal creative direction with Jay Farrar before the group’s disbandment in 1994. Jeff went on to create Wilco in the wake of the breakup, which became Tweedy’s primary creative output for decades to come. Wilco is based out of Chicago and has become a staple of the city’s music scene.

With Wilco, Tweedy ventured more into alt-rock and noise-rock innovations. With the release of Yankee Foxtrot Hotel in 2001, Wilco sold over 670,000 copies. They followed up that success with A Ghost Is Born in 2004, which won two Grammy Awards, including Best Alternative Album. In 2007, Wilco’s Sky Blue Sky peaked at No. 4 on the Billboard 200 and No. 1 on the US Independent Albums chart. It was nominated for Best Rock Album at the 50th Grammy Awards.

Decades later, Wilco is still touring and releasing new albums. Aside from continued success with Wilco, Jeff Tweedy has embarked on a successful solo career. In 2025, Tweedy released his fifth solo album, Twilight Override, an ambitious triple album. Tweedy’s band includes fellow Chicago artist Liam Kazar, along with his son Spencer Tweedy on drums. Spencer Tweedy has found success on his own, drumming for artists such as Waxahatchee, MJ Lenderman, and Case Oats. Tweedy’s other son, Sammy Tweedy, contributes synthesizer, piano, and additional vocals to the group. Fellow Chicago artists Sima Cunningham and Macie Stewart also help round out the group. Many members of the group grew up together in the Chicago area.

On March 23, Tweedy and His Band Appeared on ‘Jimmy Kimmel Live!’

The group performed the song “Lou Reed Was My Babysitter” on the late-night TV show Jimmy Kimmel Live! With a stage decorated in Christmas lights, the band was as strong as ever and delivered a stellar performance. Previously, Tweedy performed the song along with “Enough” on The Late Show with Stephen Colbert in October 2025. Colbert interviewed Tweedy, where he discussed the creative process behind the triple album and how his new band came to be. Tweedy’s band helps contribute a five-part harmony, creating a big sound for the group. Twilight Override significantly contributes to Jeff Tweedy’s prolific legacy and puts high expectations on Wilco’s next release.