The only Bob Dylan song Madonna ever liked: “Don’t ask me why I was crying”

Universal appeal is a virtual impossibility within the fickle realm of the music industry, but if there is anybody who has come close, it is surely Bob Dylan, whose timeless songwriting mastery has struck a chord with everybody from folk heroes like Pete Seeger to the queen of pop herself, Madonna.

On the face of it, it is difficult to get any further away from the folk-rooted social commentary of Dylan’s discography than within Madonna’s brightly coloured pop empire. After all, by the time that Michigan-born performer first exerted her control over the pop mainstream back in the 1980s, Dylan was already firmly planted on the upper echelon of American songwriters. While his standing in the singles charts of the day wasn’t quite as impressive as Madonna’s, his songwriting remained largely unmatched in its life-altering quality.

Even still, Dylan occupied an entirely different world from Madonna, particularly during those early days. The pop icon was about as likely to sit down and contemplate life over ‘It’s Alright, Ma (I’m Only Bleeding)’ as Dylan was to record a cover version of ‘Like A Virgin’. Nevertheless, Madonna still maintained a certain appreciation for Bob Dylan’s songwriting, even if that appreciation was largely limited to one song, in particular.

Asked during a 1994 interview with Q Magazine for her opinion on Dylan, Madonna recalled, “I used to listen to ‘Lay Lady Lay’ in my brother’s bedroom in the basement of our house,” Sharing, “I’d lie on the bed and play that song and cry all the time.” As such, Dylan’s beloved 1969 effort, apparently written for Barbara Streisand, formed a crucial part of a young Madonna’s youth.

“I was going through adolescence,” she explained. “I had hormones raging through my body. Don’t ask me why I was crying, it’s not a sad song.”

Concluding, “But that’s the only record of [Dylan’s] that I really listened to.” As far as choices for Dylan’s defining song go, ‘Lay Lady Lay’ perhaps isn’t the most obvious choice – but, then again, Madonna has never been one to follow expectations in any aspect of her existence. 

Reportedly, Dylan was first spurred to first the song for the soundtrack of Midnight Cowboy, but it never made it to the final film, instead being released as a single and becoming the songwriter’s final, thus far, top ten hit in the US. It marked a pretty stark departure from his earlier work, particularly in terms of his singing voice, which is far smoother and deeper than the ‘Like A Rolling Stone’ era nasal tones of the mid-1960s.

Madonna did not expand upon exactly what it was about the song that resonated with her during his adolescence, or why she was never inspired to explore the rest of Dylan’s expansive discography as a result. However, ‘Lay Lady Lay’ certainly stands among the songwriter’s most romantic, affecting anthems, and it is easy to see why it might resonate with a young woman trying to find her place in the world.

Although the song didn’t inspire Madonna to follow the same songwriting path as Bob Dylan, the solace that the song provided her during her younger years is a good indicator of just how universal the power of Dylan’s songwriting is.

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