The biggest challenge Madonna ever had to face: “I almost started crying”

“I think I almost started crying. I felt very intimidated.” These are not words you often hear uttered by Madonna. But what would make her feel that way? The stress of being vilified by the whole world, or even the pressure of being crowned the Queen of Pop?

No, it was none of those things – it was simply the gravitas which came with having to record ‘Don’t Cry for Me Argentina’. This may seem like a pretty trivial aspect of her life to pick up on – after all, the reception to her turn as Eva Perón in the 1996 film adaptation of the musical Evita was mixed, and it’s hardly the greatest achievement anyone would hang her hat on when looking back over the scores of Madonna’s career.

But in many ways, this would be doing a disservice to the gargantuan effort that the pop star had to pull out the bag in order to get her turn as the leading lady over the line. It was a project that, quite literally at times, relied on the blood, sweat, and tears of its artists to make it work, most of all Madonna’s.

Of course, she was more than used to being the centre of her own sonic universe, but it was perhaps one of the first times she realised that the entire weight of what she delivered would also make or break the lives of other people.

We’re all guilty of assuming that the ability to sing is one singular skill, but every different genre and style requires its own blueprint, as Madonna more than proved in this case. “It’s a whole different singing sensibility,” she later explained. “I had to seriously work with a vocal coach to sing with strength and conviction. A lot of the stuff was recorded live, and I was in the recording studio with strange producers and writers, a huge orchestra and huge shoes to fill.”

Madonna - Evita - 1996 - Alan Parker
Credit: Far Out / Buena Vista Pictures Distribution

Knowing this, despite her pop god stature, you’d think the producers might have had the grace to start off easy – but not so. “The first song they wanted me to record was ‘Don’t Cry for Me Argentina’, which is the hardest song,” Madonna incredulously added. “I think I almost started crying. I felt very intimidated. Halfway through the recording sessions, I started to relax.”

In this sense, with the big number and the largest hurdles out of the way, the rest of the journey would be more plain sailing. But Evita was plainly the job sent to test the star to her absolute limit.

Between chaotic mobs protesting the film when it began shooting in Argentina, the blistering heat of the country, and not least of all the fact that Madonna was actually pregnant at the time, it was pretty mild of her to say that the role was “difficult on every level”. Add to that equation the pressure to deliver a rousing vocal performance when all the odds seem stacked against you, and it would be a boiling pot of pressure that most would simply crumble under.

No matter how much she made it out the other side by the skin of her teeth, the fact that Madonna was able to deliver a substantive performance at all under these circumstances was nothing short of a miracle. It’s the ultimate reckoning to anyone foolish enough to believe that musical theatre is an easy cash grab for an artist, because as the Queen of Pop proved, it pushed her to breaking point more than the music industry itself ever did.

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