The Wallflowers — "One Headlight"

The Wallflowers were fronted by Jakob Dylan, and every profile and radio intro of the era mentioned whose son he was. But "One Headlight," from the album Bringing Down the Horse (1996) and sent to radio on January 21, 1997, quickly became undeniable on its own terms: introspective, built on restraint, carrying real lyrical weight without bombast. Dylan said the song is about "the death of ideas," written at a kitchen table in Los Angeles after a Virgin Records release went nowhere.

In March 1997 it achieved something no song had done before: it topped all three of Billboard's rock airplay charts at once—Modern Rock, Mainstream Rock, and Triple-A. Under that era's chart rules it never appeared on the Hot 100 itself, but it peaked at #2 on Hot 100 Airplay and spent 70 weeks on that chart, plus five weeks at #1 in Canada. For most of a year you could not turn on rock radio—modern, mainstream, or adult-alternative—without finding it.

The Grammys sealed the moment: at the 1998 ceremony, "One Headlight" won Best Rock Song and Best Rock Performance by a Duo or Group with Vocal. The song's stature has only grown—Rolling Stone and MTV ranked it #58 on their 2000 list of the 100 greatest pop songs, and in 2021 Billboard ranked it #1 on its list of the greatest adult-alternative songs. Not bad for a guy who spent the whole run being asked about his dad.