The 1969 Bob Dylan song that makes Madonna cry every time she hears it: “Don’t ask me why”

The goddess stature of Madonna makes it hard to ever believe that she could be vulnerable, or afraid, or emotional.

But beneath the veneers of high priestesses and disco ravers, the reality is that she is only human. A human who can still very much fall off stages, or have her clothes nicked at Coachella. Those things are all par for the course and prove definitively that even Madonna can still be humbled at times. 

Yet even despite all of that, it was in a far quieter moment, long before the bright lights of fame came calling, that the future star perhaps felt at her most emotional ebb. Of course, the simple fact of being a teenager can bring this on naturally, but in her case, there was one man specifically who was at the root of the teary problem.

That was an issue that Bob Dylan could never have anticipated causing when he released ‘Lay Lady Lay’. The song obviously became a masterful standard of rock shortly after it was released in 1969, leading it to be covered and rehashed by countless artists over the years, but on Madonna in particular, it had a possibly unexpected effect.

Every time she heard it as a young girl, it automatically made her burst into tears. “I used to listen to that one record, ‘Lay Lady Lay’, in my brother’s bedroom in the basement of our house,” she later recalled. “I’d lie on the bed and play that song and cry all the time.” But what were the reasons for that, you ask? She doesn’t even know.

Madonna could only offer up the justification, ”I was going through adolescence, I had hormones raging through my body. Don’t ask me why I was crying, it’s not a sad song. But that’s the only record of his that I really listened to.” In doing so, though, she might have just unearthed that Dylan had a secret talent. 

As she correctly pointed out, ‘Lay Lady Lay’ is by no means forlorn or tear-inducing in the most conventional manner. But maybe there was a hidden spark, masked within Dylan’s low and tender crooning on the track, that hit people right in the heart and made them emotional for reasons unknown, particularly for teenage girls.

In that respect, if Dylan had been wise enough, he could have made an absolute killing as the next adolescent heartthrob who would not only have girls falling at his feet but also sobbing uncontrollably into his arms, at least if Madonna was anything to go by. Something tells me that he would have absolutely run a mile from anything remotely near this, though.

But just like the rest of us, there was always bound to be a small piece of heartbreak in ‘Lay Lady Lay’ that has formed a lump in Madonna’s throat ever since, no matter how many years have passed since she would sit crying in her brother’s bedroom. In a lot of ways, it’s that shred of an old story that makes her more human than anything else.

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