Interview: Steve Wynn of Dream Syndicate - Medicine Show at 40, Early Band History & Future Plans

In this episode of LEGENDS: Podcast by All Day Vinyl, host Scott Dudelson sits down with Steve Wynn — singer-songwriter and founding member of The Dream Syndicate — to celebrate the 40th anniversary deluxe edition of their landmark album Medicine Show.

Wynn revisits the band’s origins in early-1980s Los Angeles, tracing how punk energy and the Paisley Underground scene shaped their sound. He recalls the band’s first rehearsal at Dennis Duck’s house in 1982, which set the creative direction leading to their classic debut The Days of Wine & Roses.

The conversation dives deep into the making of Medicine Show after signing with A&M Records — from working with producer Sandy Pearlman and experimenting with slower, more dynamic arrangements to enduring five grueling months of recording that strained band relationships. Wynn reflects on the record’s darker, Southern-Gothic-inspired lyrics born from life on the road.

They also explore the band’s major tours (opening for U2 and touring with R.E.M.), lineup changes, near breakups, and eventual reunions that produced new albums and a revitalized modern lineup. Wynn opens up about the long legal battle to reclaim the Medicine Show masters, the 35-year reversion process that made this reissue possible, and what fans can expect from the deluxe box set — including remasters, live shows, rehearsal tapes, and rarities. He also explains why the original album remains unavailable on streaming despite the reissue.

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