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Heralded as leaders of the Paisley Underground (the neo-'60s Southern California scene that included the Bangles, Green on Red, and the Rain Parade), the Dream Syndicate were by far the most outside band in the bunch, challenging audiences to feedback fests and endless jams. After four albums on four labels and a change in musical direction (less Lou Reed, more Neil Young), the Syndicate called it quits and Wynn embarked on a solo career. For Kerosene Man (1990) and Dazzling Display (1991), he relied on his steady songwriting, unique vocal style, and a bunch of friends (including Peter Buck of R.E.M.) for the recordings. Fluorescent (Mute, 1994) was a subdued, semi-folk record, but his side project Gutterball (including Bryan Harvey and Johnny Hott of House of Freaks and Bob Rupe of the Silos) was a loose and drunken rock & roll ramble. The solo work kept on coming: Melting in the Dark (1996), Sweetness & Light (1997), My Midnight (1999), and Momento (2000), the latter a collaboration with Australian Blonde, a Spanish alternative rock band led by Wynn's friend Paco Loco. But Wynn was ultimately destined to lead a band again, and with his combo the Miracle 3 he released the double-disc set Here Come the Miracles (2001), Static Transmission (2003), and the post-millennium panic-inspired ...Tick...Tick...Tick (2005). The same year as ...Tick...Tick...Tick, Wynn summed up his post-Dream Syndicate career to date with the accurately titled 17-track compilation What I Did After My Band Broke Up, which included a bonus disc of Wynn performing some of his favorite songs on piano.
In 2007, Wynn and Paco Loco recorded a second album together for a Spanish label under the name Smack Dab. A voyage to Slovenia to collaborate with Chris Eckman of the Walkabouts resulted in the 2008 album Crossing Dragon Bridge; the same year, Wynn launched another side group, the Baseball Project, in which Wynn teamed up with Peter Buck, Scott McCaughey (of the Young Fresh Fellows), and Linda Pitmon (from the Miracle 3) to write and sing songs about his favorite game on the album Vol. 1: Frozen Ropes and Dying Quails. Wynn and the Miracle 3 returned in 2010 with the album Northern Aggression, while the Baseball Project came back for a second inning with 2011's Vol. 2: High and Inside; that same year, Wynn's recorded guest spots included Let It Beard by Boston Spaceships and The Journey Is Long by the Jeffrey Lee Pierce Sessions Project. In 2013, Wynn paid homage to one of his key influences with Wynn Plays Dylan, a limited-edition live album from a show with Wynn performing a set of Bob Dylan tunes, and in 2014, Wynn and the Baseball Project teamed up again (this time with R.E.M.'s Mike Mills joining the lineup) for an album simply called 3rd. Wynn's two albums with Paco Loco also received a belated American release in 2014 on the collection Sketches in Spain. ~ Denise Sullivan & Mark Deming, Rovi