He later attended University High School (Los Angeles) with classmates Darby Crash and Pat Smear who would later go on to form the Germs.
[2] After Suspects disbanded, Wynn formed the trio 15 Minutes with two members of Alternate Learning, bass player Carolyn O'Rourke and drummer Eric Landers.
Wynn broke up The Dream Syndicate in 1989 to redefine (or "undefine") himself,[7] and has since released a number of solo albums exploring various musical styles.
His first solo album, Kerosene Man (on which Dream Syndicate bassist Mark Walton played also) included a duet with Johnette Napolitano of Concrete Blonde, backing work by bassist Fernando Saunders, drummer D. J. Bonebrake from the L.A. punk band X, Howe Gelb of Giant Sand and saxophonist Steve Berlin from Los Lobos.
He toured behind these albums in the following years with his band the Miracle 3, consisting of Jason Victor, Dave DeCastro and Linda Pitmon, often augmented live and in the studio by Chris Cacavas (Green on Red, The Dream Syndicate) on keyboards.
Dutch native and resident Erik Van Loo substituted for DeCastro on several tours and on the 2006 Live Tick album, recorded in Geislingen, Germany.
[10] In 1985, Wynn wrote a collection of songs with Dan Stuart of Green on Red, and recorded and released them as Danny & Dusty, The Lost Weekend.
In the 1990s, he was a part of the indie supergroup Gutterball along with Stephen McCarthy of The Long Ryders, Bob Rupe of The Silos and Cracker, and Bryan Harvey and Johnny Hott of House of Freaks.
The band's debut album Volume 1: Frozen Ropes and Dying Quails came out the following April with their first live performance coming on the Late Show with David Letterman.
The album Crossing Dragon Bridge, recorded in Ljubljana, Slovenia and produced by Chris Eckman of The Walkabouts, also came out in 2008 and was called "Wynn's masterpiece" by Thom Jurek of AllMusic.