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 has 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 in the late '80s when he formed 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, but it sold poorly and Virgin dropped the band.

Dylan assembled a second version of the Wallflowers — guitarist Michael Ward, bassist Greg Richling, and drummer Mario Calire — keeping only Jaffee. 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 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, and while the media naturally played up Dylan's connection to his iconic father, the Wallflowers had 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, and in 1998 "One Headlight" won Grammys for Best Rock Song and Best Rock Performance by a Duo or Group with Vocal.

The obvious next move would have been to rush out a third album, but Dylan and the Wallflowers instead took a long four-year break from recording, returning in October 2000 to release Breach. The album, although quite impressive, went largely ignored. The more mainstream Red Letter Days appeared a year later in 2001, and following a two-year hiatus, Rebel, Sweetheart was issued in 2003, closing out the band's deal with Interscope. Dylan signed a solo contract with Columbia Records, his dad's longtime label, in 2006, 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, leaving the status of the Wallflowers up in the air.