The most iconic Madonna moments that need to be in her biopic

After moving to New York in 1978, Madonna soon fell into the world of art royalty. She partied with Keith Haring and Andy Warhol, and even dated the ‘enfant terrible’ of street art Jean-Michel Basquiat. The love affair was short-lived, with the pair drifting apart as Basquiat grew closer with Warhol and Madonna being distracted by recording her explosive debut Like A Virgin, but there was clearly lasting affection between the pair. Speaking to the New Strait Times in the wake of Basquiat‘s death, Madge recounted: “When I heard that Jean-Michel had died, I was not surprised. He was too fragile for this world.”

Perhaps Madonna’s most iconic fashion look, the star’s Blond Ambition tour in 1990 stunned audiences with explosive choreography from voguing legends from the New York ballroom scene, a headline-grabbing mix of Catholic imagery and BDSM, a $2 million stage set, and, of course, the Jean Paul Gaultier Cone Bra.

Madonna personally wrote a letter to Gaultier to request that he design the costumes for the tour – the pink conical bra reportedly took months of collaboration, with fittings taking place in both New York and Paris.

It was also the Blond Ambition tour where Madonna – preparing to take the stage at Toronto’s SkyDome – was threatened with arrest by officers who asked her to not simulate masturbation. Madonna’s response? ”I’m not changing my fucking show.”

Another iconic Madonna moment arrived just one year later with her performance of “Sooner or Later” from the soundtrack to 1990 crime thriller Dick Tracy, in which she also starred. The track won the Oscar for Best Original Song that year, and Madonna’s escort for the awards was none other than Michael Jackson. The king and queen of pop were united. 

In 1992, Madonna released an elaborate coffee table book created in collaboration with fashion photographer Stevel Meisel and Fabien Baron (Harper’s Bazaar). Tackling themes of homophobia, AIDS hysteria, and female desire, the book sold out its limited 1.5 million printing in a matter of days. The book itself was bound in metal and sealed in a Mylar bag to evoke condoms.

Continuing a transgressive streak in her career, Madonna shocked households across America with her first appearance on CBS’ Late Night Show with David Letterman, which stands as the most censored episode in American talk show history. The interview began with Letterman introducing Madonna as “one of the biggest stars in the world [... who has] slept with some of the biggest stars in the industry”.

The subsequent exchange was filled with controversial moments, with Madonna saying ’fuck’ 14 times, inviting Letterman to sniff her underwear and admitting that she had smoked weed before arriving at the studio.

While there was uproar from the studio audience, Madonna later claimed that she was attempting to make a stand against television censorship. Speaking to Spin Magazine the following year, Madonna explained: “You can show a person getting blown up, but you can’t say fuck? It’s such hypocrisy [...] The way [Letterman] introduced me was derogatory, so my whole thing was, okay, if that's how you want to play it, you cannot beat me at this game.”

Perhaps the best VMA moment of all time, Madonna is being interviewed about her upcoming work, when a makeup compact goes flying over her head. She stops, visibly stunned, and turns around to see what it is. From a distance, you can hear “Hi!” and the host responding, “Hi, Courtney!” in a similar tone to a children’s presenter. The camera pans down, and we see Courtney still throwing a neverending array of compacts their way. What are these compacts actually? How does she have so many compacts in her purse? The mystery remains unsolved.

Ever since Madonna first sang the line, “Don’t cry for me Argentina”, musical theatre has never been the same. The then-36-year-old wowed audiences in the role of Eva Peron, Argentina’s chic, noble demagogue. The performance itself is a straight-up classic: Madonna has to spend the first part in unflattering Depression garb, while pretending to be a 15-year-old country girl who tangoes her way to a better life in Buenos Aires. In later scenes, she’s so fashionable and magnetising that even her casket self is well-dressed.

Who can forget that moment at the 2003 MTV VMAs when Britney infamously kissed Madonna during a joint performance of Madonna’s “Like a Virgin” and “Hollywood”. After the kiss – which is often cited as one of the most iconic moments in the history of the awards – the camera cuts to Justin Timberlake’s face, unamused.

Another celebrity, another kiss. At the closing day of Coachella in 2015, Madonna appeared with Drake after he played his own song named after the pop icon. She went onto sing her track “Human Nature” before kissing the rapper and leaving the stage. 

However, the moment made headlines for all the wrong reasons when photographs appeared to show Drake grimacing in the moments following the lip-lock. The rapper later addressed the issue on Instagram, saying: “Don‘t misinterpret my shock!! I got to make out with the queen Madonna and I feel 100 per cent about that forever.”

After first clashing in 2011 over allegations of plagiarism and jealousy, Madonna and Lady Gaga’s decade-long feud is no secret. But the pair appeared to put their differences behind them at the 2019 Oscars, following Mother Monster’s big win for Best Original Song for A Star Is Born. Regardless, we’d love to see Madonna go deeper on the infamous beef. *Sips tea*