Why didn’t Bob Dylan ever have a number one pop hit?
Across the history of popular music, few artists are as influential as Bob Dylan. The legendary singer-songwriter managed to change the way popular music was perceived, radically altering the format from one of light entertainment to true social importance. Along the way, Dylan was at the forefront of the rock revolution and held tight to the changes. When album-oriented rock became huge, Dylan was there to benefit from the evolution. But during the age when singles dominated the pop and rock markets, he was able to string together a successful bunch of hits.
The only problem was that Dylan never managed to score a number one hit. His influence spurned other chart-topping songs, with everyone from The Beatles to Stealers Wheel taking Dylan’s signature style and creating hits of their own. Famously, Dylan had some major selling singles, including a few that sold well enough to almost top the charts in both the US and the UK. Despite this, he never hit the very top, stalling out at number two on the Billboard Hot 100 two different times across his career.
Neither of Dylan’s first two singles, ‘Mixed-Up Confusion’ or ‘Blowin’ in the Wind’, appeared on any major charts. But his third single, ‘The Times They Are a-Changin”, was a genuine top ten hit in the UK in early 1965. The song first appeared on Dylan’s album of the same name in 1964, by which point he decided that he wouldn’t release singles in America. No singles were released from that year’s Another Side of Bob Dylan, but the singer’s popularity was hitting a fever pitch just as he decided to shift focus.
No longer interested in protest music, Dylan decided that he wanted to embrace the rock revolution that was going on around him. So, as he assembled 1965’s Bringing It All Back Home, the legendary pioneer decided to release the album’s opening track as a single. ‘Subterranean Homesick Blues’ was a pop chart breakthrough for Dylan, with the singer scoring his first top 40 hit in the US with the track. The song was an even bigger hit in the UK, where it hit number nine on the UK Singles Chart, matching the peak that Dylan had reached with ‘The Times They Are a-Changin”.
‘Maggie’s Farm’ was then released as a single in the UK, reaching number 22 in 1965, but Dylan withheld it from getting an American single release. Instead, he shifted his focus to Highway 61 Revisited, a full embrace of rock instrumentation. Once again, Dylan wanted the album’s leadoff track to double as its first single. He was probably at the peak of his cultural powers and commercial popularity when ‘Like a Rolling Stone’ hit the airwaves on July 20th, 1965.
Despite its six-minute-long structure, ‘Like a Rolling Stone’ wound up being Dylan’s most commercially successful single. A major transatlantic hit, ‘Like a Rolling Stone’ peaked at number two in the US, held out from the top spot by The Beatles track ‘Help!’. In subsequent years, John Lennon would often credit Dylan for inspiring him to take a more sincere and personal approach to lyrics, and that influence probably (somewhat ironically) kept him from landing a number one pop hit.
‘Like a Rolling Stone’ was also a success in the United Kingdom, where it gave Dylan a new peak at number four on the UK Singles Chart. The week it hit its peak, ‘Like a Rolling Stone’ was kept out of the top spot by The Rolling Stones themselves, who had landed a number one hit with ‘(I Can’t Get No) Satisfaction’. Also keeping Dylan from the top of the UK charts were Sonny and Cher, who were at number two with ‘I Got You Babe’, and The Walker Brothers, who were at number three with ‘Make It Easy On Yourself’.
Dylan would score another cross-continental top ten hit with ‘Positively 4th Street’, but then would enter a brief fallow period as ‘Can You Please Crawl Out Your Window?’ and ‘One Of Us Must Know (Sooner or Later)’ failed to reach the same heights. Undeterred, Dylan released ‘Rainy Day Women # 12 & 35′ in 1966, giving him his second and final number two hit in the US. This time, it was The Mamas and The Papas’ ‘Monday, Monday’ that kept Dylan from securing his number one hit.
As Dylan recuperated from his motorcycle accident in the summer of 1966, his music shifted from commercial folk rock to country and roots rock. His recordings with The Band would later be assembled into The Basement Tapes. Columbia attempted to cover his absence by releasing ‘Leopard-Skin Pill-Box Hat’ as a single in America in 1967, but Dylan wouldn’t release another single until 1969’s ‘I Threw It All Away’. ‘All Along The Watchtower’ would be released as an A-side in the Netherlands, but the song’s real chart success came through Jimi Hendrix’s cover versions, which became Hendrix’s sole top 20 hit in the US.
1969’s ‘Lay Lady Lay’ would be Dylan’s final top ten hit in either the US or the UK, landing at number seven in America and number five in Britain. 1973’s ‘Knockin’ on Heaven’s Door’ peaked just outside the top ten in both countries, but that would be Dylan’s reign as a prominent pop music singles artist. He would occasionally flirt with topping the charts, even securing a number one song on the Billboard Digital Rock Chart with his 2020 track ‘Murder Most Foul’. But on the major pop charts, apart from occasional appearances in the top 40 with songs like ‘Tangled Up in Blue’, ‘Baby, Stop Crying’, ‘Gotta Serve Somebody’ and ‘Dignity’, Dylan would never again seriously contend for a number one hit.
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