Steve Wynn went from the lower reaches of the Los Angeles underground music scene to major critical acclaim practically overnight with the release of the Dream Syndicate's debut album, The Days of Wine and Roses, in 1982. It proved to be the first act in a long and fascinating career in which Wynn matured into one of the canniest songwriters in rock, penning smart, flinty lyrics that told perceptive tales of human behavior both noble and otherwise, married to tough, engaging melodies full of muscular guitar work. Wynn launched his solo career with 1990's Kerosene Man and 1991's Dazzling Display, both of which found him working with an impressive variety of collaborators. From the '90s onward, Wynn would follow his muse through a number of creative paths, and while his early work often revealed the influence of Lou Reed and Bob Dylan, his more mature material (as evidenced by 2001's Here Come the Miracles and 2010's Northern Aggression) showed he had grown into an unsung heir to their place in rock songwriting.

After graduating from the University of California at Davis and following a stint with his requisite new wave band of that era, Suspects, Wynn took a cross-country trip in search of Alex Chilton, one of his spiritual musical mentors and a mysterious figure since his days with power pop legends Big Star. Interestingly, by the time Wynn found him and returned to California, the underground rock scene was in the middle of a full-on guitar rock revival, thanks in part to fellow Chilton devotees R.E.M. and the Replacements; Wynn took it as his cue to embrace the feedback-flooded sounds of the Velvet Underground. Borrowing his name from the VU's heritage, he called his new band the Dream Syndicate, after an early experimental group featuring John Cale.

Heralded as one of the leading bands 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.

In 2012, after several European tours in which Wynn performed Dream Syndicate material with the Miracle 3, he unveiled a new lineup of the band at Festival BAM in Barcelona, Spain. This edition featured previous members Wynn, Dennis Duck, and Mark Walton, as well as guitarist Jason Victor, who had played with Wynn in his solo projects. The revived Dream Syndicate staged several concert tours, mostly in Europe, before returning to the studio to cut a new album. How Did I Find Myself Here? was released by Anti- in September 2017, and featured guest vocals from Kendra Smith. As the return of the Dream Syndicate boosted Wynn's profile, Omnivore Records released expanded and remastered editions of his first two solo efforts, Kerosene Man and Dazzling Display, in April 2018. ~ Denise Sullivan & Mark Deming, Rovi