Alvin's first solo album, entitled Romeo's Escape was released in 1987 and was critically lauded, but didn't fare well in the marketplace.Alvin was subsequently dropped by his label Columbia Records. Alvin suffered health problems which sidelined him for a while, except for a wild tour with friends Mojo Nixon and Country Dick Montana as the Pleasure Barons, which was described as "a Las Vegas revue from acts who aren't going to be asked to play Vegas". (A live album was released of a second Pleasure Barons tour in 1993.)

In 1989, Dwight Yoakam scored a hit on the country charts with Alvin's song "Long White Cadillac", and Alvin used the royalties to start work on his second solo set, Blue Blvd. Released by the California-based roots-music label Hightone Records in 1991, Blue Blvd received enthusiastic reviews and sold well enough to re-establish Alvin as a significant artist in the roots rock scene.

After releasing Museum of Heart in 1993, Alvin began to turn his attention to acoustic music with 1994's King of California, and over the next several years Alvin moved back and forth between hard-edged roots rock and more introspective acoustic material that still honored his influences (and allowed him to display a greater range as a vocalist).

In 2000, Alvin recorded a collection of traditional folk and blues classics, Public Domain: Songs From the Wild Land, which earned him a Grammy award for Best Contemporary Folk Album.