Bob Dylan Never Had A No. 1 Hit — But His Son Jakob Topped Three Charts At Once In 1997

Bob Dylan may be one of the best-known singer-songwriters of the 20th century and a foundational influence for countless musicians who came afterward. Yet despite all the accolades and esteem showered upon him over decades, he's never had a No. 1 song. There's no mistaking his chart success, though — he's banked a whopping 23 songs on Billboard's Hot 100, four of which cracked the Top 10. But his son Jakob has racked up an historic triple play of No. 1 chart spots, all with a single song that had the juice that Dylan Sr. never quite captured. It's a case of a newcomer cub son outshining his lionized father, at least where topping the charts is concerned.

Even with his impressive roster, Bob Dylan missing the top spot is a notable omission in an otherwise legendary career. And Dylan's talents have become so renowned, there are Harvard courses dedicated to studying his works. So maybe it isn't such a surprise that he handed down his talent to his son or that Jakob was destined to become a hitmaker in his own right in the late '90s. Only this time, the junior Dylan was able to capture the lightning in a bottle that his father kept missing. 

When The Wallflowers dropped its mega-popular single "One Headlight" in 1997, the resemblance between Jakob Dylan's voice and his father's was instantly recognizable, though the younger Dylan's diction was much clearer. But it was the songwriting talent that shone through the strongest, with lyrics that resembled the older Dylan's most poetic. A passage like "She said, 'It's cold, it feels like Independence Day / And I can't break away from this parade'" could easily fit into a modern Bob Dylan tune, but Jakob gives it his own unique spirit.

The big difference here was in how the song was received by the listening public. Not only did the song score a contemporary rock hat trick by topping the Adult Alternative Airplay, Modern Rock, and Mainstream Alternative charts, but it also became the first single to do so. It also won two Grammys and went on to be named the No. 1 Adult Alternative Rock song of all time — a title it has held for a mind-blowing 30 years. It's a striking accomplishment that heightened the Dylan family's musical legacy. The Wallflowers never repeated the success of "One Headlight," despite releasing other singles. Even with the public wondering whatever happened to The Wallflowers these days, Jakob Dylan achieving chart-topping success is a feather in the cap of the Dylan musical legacy.