Being the son of one of the most influential, innovative, eccentric, and unique songwriters in the history of Western pop music probably opened some doors for Jakob Dylan when he started his own musical career, but being Bob Dylan’s son was just as likely a heavy load to carry as well, and the good news is that the younger Dylan handled the pressure with relative élan. Born in 1970, Jakob Dylan was raised in Los Angeles by his mother, Sara Lowndes, after his parents’ divorce in 1977. He studied at private schools in L.A. and New York, and eased into the music business during the late ’80s by forming the Wallflowers with guitarist Tobi Miller, keyboard player Rami Jaffee, bassist Barrie Maguire, and drummer Peter Yanowitz. Featuring a classic heartland sound that was closer to Tom Petty & the Heartbreakers or John Mellencamp than it was to anything Bob Dylan recorded, the band signed to Virgin and released a self-titled debut album in 1992. The record sold poorly, however, and Virgin dropped the band.
Dylan assembled a second version of the Wallflowers, one in which he and Jaffee were joined by a trio of new members — guitarist Michael Ward, bassist Greg Richling, and drummer Mario Calire. The “new” group signed to Interscope Records and recorded its second album with producer (and Dylan family friend) T Bone Burnett. Bringing Down the Horse was released in 1996, producing the alternative radio hit “6th Avenue Heartache.” A second single from the same album, “One Headlight,” followed later in the year, and by the spring of 1997 it had become a Top Ten hit, firmly establishing the Wallflowers as a legitimate commercial band. While the media naturally played up Dylan’s connection to his iconic father, the Wallflowers possessed their own sound, and Jakob’s similarities to his dad as both a singer and a songwriter were only occasional at best. A third single from Bringing Down the Horse, “The Difference,” was issued in 1997, and the album hung on as a big seller throughout 1997. One year later, “One Headlight” won Grammys for Best Rock Song and Best Rock Performance by a Duo or Group with Vocal.
The typical next move would have been to quickly record a third album, but Dylan and the Wallflowers decided to take a long break from the studio instead. They returned in October 2000 with Breach, a fairly impressive effort that was largely ignored by mainstream radio. The more commercial Red Letter Days appeared a year later in 2001, and the band closed out its deal with Interscope by issuing Rebel, Sweetheart two years later.
Dylan signed a solo contract in 2006 with Columbia Records, his dad’s longtime label, and issued the acoustic-based Seeing Things — produced by Rick Rubin and recorded at Rubin’s Hollywood Hills studio — under his own name in 2008. Although the move seemingly left the status of the Wallflowers up in the air, the band reconvened one year later to tour in support of a greatest-hits album. It wasn’t long before Dylan turned back to his solo career, though, and he released the sophomore effort Women and Country in 2010.