The Beatles Stopped Bob Dylan’s Best Shot at Having a No. 1 Hit

Bob Dylan had cemented his legacy as a folk music legend before he met The Beatles. The Fab Four already loved his music before their in-person encounter. John Lennon gave Dylan high praise/a backhanded compliment when he said Yoko Ono was as important a singer as the troubadour. They were musical icons of the 1960s, but The Beatles denied Dylan his best shot at having a No. 1 hit on the Billboard charts.

The Beatles’ song ‘Help!’ stopped Bob Dylan from having a No. 1 hit in 1965

Escaping The Beatles’ shadow on the Billboard charts was next to impossible in the mid-1960s. The band tallied 47 of their 64 top-100 singles between 1964 and 1966. That run coincided with some of Dylan’s finest work of the decade. That included 1965’s Highway 61 Revisited.

Dylan had an incredible peak in the 1960s. He was also one of several classic rock artists without a No. 1 hit, and The Beatles blocked his best chance to reach the summit.

“Like a Rolling Stone,” the lead track on Highway 61 Revisited, reached No. 2 on the Billboard singles chart in early September 1965. It stayed there another week before starting its slide out of the top 10. The Beatles held the No. 1 spot both weeks with “Help!” per Billboard. 

That 1965 rise to the penultimate spot was Dylan’s best shot at No. 1. “Rainy Day Women #12 & 35” rose to No. 2 for a week in May 1966 only for The Mamas & The Papas’ “Monday, Monday” to hold the former Robert Zimmerman at Bay.

The Beatles stopped Bob Dylan’s best shot at earning a Billboard No. 1 hit, but it didn’t prevent him from remaining a fan of the group. And vice versa.

John said hearing Dylan’s music affected his songwriting. Both artists absorbed the other’s influence after The Beatles first met Dylan in 1964. 

He introduced them to pot. They opened their minds, altered their sound, and charted the course for the next half-decade of pop music. They showed him the power of electric guitars. He went electric at the Newport Jazz Festival in 1965 and proved that you could still be a stellar singer-songwriter even without an acoustic guitar. 

It could be a coincidence that some of Dylan’s career-defining albums — Highway 61 Revisited, Blonde on Blonde, John Wesley Harding — came after he met the Fab Four, but it doesn’t seem like one. John likewise took inspiration from his counterpart and wrote several Beatles songs inspired by Dylan, including two from Rubber Soul.

Despite their closeness and fondness for each other’s work, Dylan and The Beatles rarely crossed paths professionally.

George Harrison was the only member of The Beatles Dylan worked with

Their peak years overlapped, and the individual members of The Beatles had solo careers extending into the 1980s and beyond. Yet Dylan only ever worked with one of the Fab Four — George Harrison.

The freewheelin’ troubadour joined Harrison’s Traveling Wilburys supergroup in the late 1980s. What started as an impromptu recording session with George, Jeff Lynne, and Roy Orbison kept adding members. George phoned Dylan to ask about using his studio, and Tom Petty tagged along after Harrison picked up his guitar from Petty’s house. The short-lived supergroup became a hit with fans. It produced a multi-platinum debut and one more album, but Dylan blamed the Traveling Wilburys for his worst-reviewed album, 1990’s Under the Red Sky.

Dylan almost recorded with Ringo Starr in 1987, but the singer-songwriter stood up The Beatles drummer. It might have been for the best — Ringo’s solo album never saw the light of day. That was three years after Dylan had his last charting single. “Sweetheart Like You” reached No. 55 in early 1984.

The Beatles stopped Bob Dylan from having a No. 1 hit in 1965. It was also his best chance as “Like a Rolling Stone” held at No. 2 for two weeks as “Help!” claimed the top spot. Still, the singer-songwriter didn’t hold a grudge. He joined Fab Four guitarist George Harrison on two Traveling Wilburys albums decades later.

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