In 1989, Russell joined forces with bassist Jason Hiller, keyboard players Dave Sobel and Chris Joyner, and drummer Craig Aaronson to form the Freewheelers, whose sound was influenced by roots rock and vintage R&B. The band developed a following on the L.A. club circuit and landed a deal with David Geffen's DGC Records. However, their self-titled debut album was released the same day as another DGC release, Nirvana's Nevermind, and The Freewheelers got lost in the shuffle. DGC dropped the Freewheelers; they landed another record deal with Rick Rubin's American Recordings and released their sophomore album, Waiting for George, in 1996, by which time John Hofer had taken over on drums. The album didn't sell much better than the debut, and the group would relocate to Portland, Oregon before breaking up. Russell continued writing songs and recording demos, and he was invited to join a band called Federale with Marc Ford of the Black Crowes. Federale was signed to a record deal with Geffen Records, and the band was about to begin work on their debut album when Geffen was purchased by Interscope Records and Federale was dropped.
By this time, Russell had already released a collection of demos and home recordings, 1997's Lowdown World, and after the breakup of Federale, he began recording original material that formed his second solo album, 1999's Down at Kit's, which was dominated by instrumental material. One of the tracks, "Fried Bananas," made its way onto the soundtracks of several TV shows, which provided an unexpected windfall for Russell. He began dabbling in production, working on albums by Richmond Fontaine, Fernando, Caleb Klauder, and Mel Brown. In 2000, he struck a deal with a new label, eMusic, and recorded an album titled Skulltown. However, eMusic went out of business before the set could be released, and some of the tracks appeared on an odds-and-ends compilation titled Spare Change, issued in 2001. Russell stayed busy as a producer and sideman over the next several years, and he co-produced the 2007 debut album by Sarabeth Tucek in tandem with Ethan Johns. Johns also helped produce Russell's next album, 2007's Repairs.
2010 saw the release of Clara Obscura, the debut album from the Relationship, a side project of Weezer guitarist Brian Bell, with Russell serving as producer. Also in 2010, Russell dropped a vinyl EP, Motorbike, which was a preview of 2011's The Invisible Audience, an ambitious 75-minute album that featured 25 original songs. Remarkably, it was followed in 2013 by The Invisible Audience Companion, which collected 12 more songs from the same sessions. In 2012, Russell completed another album, How I Won the West, that received a belated digital release in late 2017. 2013 saw Russell record a homemade album on a four-track cassette machine, Sakes; fittingly enough, it was released on cassette-only in a limited edition of 100 copies. In 2016, Brian Bell recruited Russell to co-write two songs with him for Weezer's 2016 release Weezer (White Album). The same year, Russell and Big Star drummer Jody Stephens released a collaborative album, Those Pretty Wrongs, and Russell took part in several Big Star's Third concerts, which re-created the songs from the group's legendary final album. In 2017, the Spanish label Hanky Panky Records released Selective Memories: An Anthology, a two-disc collection that spanned Russell's career, from unreleased Bootheels demos to a track from upcoming album Medium Cool. ~ Mark Deming, Rovi