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Top 40 Madonna Moments Madonna at 40 years into her career

Top 40 Madonna Moments

Madonna at 40 years into her career

by Alarcon, Founder / Managing Editor
first published: March, 2023
You can never put a bad feminist down

Madonna is embarking on a world tour this summer in celebration of her 40th anniversary in the business. In a press release, she said the tour’s setlist would span her entire discography – her first career retrospective and it’s being touted as "the biggest tour she's ever done." To celebrate this momentous news, I’ve put all of my knowledge of Madonna to good use and compiled the definitive list of her top 40 moments of all time.


40: DATING BASQUIAT
Madonna and Jean-Michel Basquiat (main photo) dated for most of 1982 while she was making her first album and he was juggling his first two solo shows (and selling every painting he showed, thanks in part to Rene Ricard’s fantastic Artforum profile, “The Radiant Child”). The relationship ended in early 1983 when she left him for the last time over his heroin addiction. He then demanded that Madonna return all of the artwork he made for her, painted over each canvas in black, then burned them, and tossed them in a back alley behind his studio. Artistic temperament!

 

39: FORMING EMMY AND & THE EMMYS

In 1980, Madonna formed and led Emmy & the Emmys, a stripped-down post-punk four-piece that spent a year together searching for a direction. Sometimes they sounded like The Pretenders, sometimes they sounded like the Banshees, and this early version of “Burning Up” sounds an awful lot like Blondie. There’s an alternate timeline where Madonna went on to lead a very Kim Gordon-like life.

 

38: BECOMING PART OF HIGHER ACADEMIA
As the leader of New Feminism, Madonna broke down the hierarchies of race, class, and gender to the point where prestigious universities such as Harvard, Princeton, and UCLA all offer courses on Madonna Studies. Pundits (all male, naturally) still call these courses “defrauding students of higher education” – the same thing they said when Andy Warhol and his soup can paintings appeared in Ivy League curriculums.

 

37: HER LETTERMAN APPEARANCE IN '94

In one of the only late night talk show appearances that has its own extensive Wikipedia page, Madonna used the word “fuck” fourteen times, handed Letterman the panties she had just taken off backstage (and then told him to sniff them), refused to kiss some random creep in the audience that Letterman kept pressing her on, called him a “sick fuck,” called him uncool, and proclaimed that “money made [him] soft.” The whole appearance was her striking back at the host for making her the punchline of a decade’s worth of sexist and misogynistic on-air jokes. 

 

36: WEARING THAT CONE GAULTIER BRA
gaultier
Iconic!

 

35: OPENED FOR THE SMITHS AT DANCETERIA ON NYE (According to Johnny Marr)

On December 31, 1983 at approximately 9PM, Madonna performed on the third floor of Danceteria in Manhattan, New York. Around four hours later on January 1, 1984 at approximately 1AM, The Smiths made their US debut on the first floor of the same club. While Madonna and the Smiths never stepped foot on the same stage, that fact has never stopped Johnny Marr from regaling any impressionable, young music journalist who’ll listen with the story that “Madonna opened for the Smiths.” He’s repeated the story so much, we all just sort of go along with Johnny’s account of events because no one has the heart to tell him that The Smiths were actually playing mop-up to Madonna, Lovebug Starski, Whodini, and Kurtis Blow that night. Besides, why let the truth get in the way of a great story?

 

34: HER ACCEPTANCE SPEECH AT THE 2016 BILLBOARD WOMAN OF THE YEAR AWARDS
Aged pearl-clutchers in the suburbs still deny it, but for several decades, Madonna was the face of New Feminism who continuously and unapologetically spit in the face of Old Feminism. While Prince, Steven Tyler, George Michael, and her other male contemporaries could incorporate sexuality into their music and receive praise, Madonna did it and was called a whore. In her acceptance speech after winning Billboard’s Woman of the Year Award in 2016, she put a spotlight on all of that sexism, misogyny, and the criticism she faced over the decades. As she said that night, “If you [were] a feminist, you didn’t have sexuality; you denied it. So I said, ‘Fuck it, I'm a different kind of feminist. I'm a bad feminist.’”

 

33:  STAGING A MOCK CRUCIFIXION AS THE CENTREPIECE OF HER 2006 TOUR
cornellWhat’s the big deal? Chris Cornell made a career out posing like he was hanging off a cross. He even wrote a song about it.

 

32: GRACIOUSLY FORGAVE ELTON FOR BEING SUCH A PILL TO HER ALL THESE YEARS

What was that bitter queen’s problem anyway?

 

31: MADE HER OWN WAY
own wayMadonna moved from Michigan to New York City with a duffel bag, $35 in her pocket, and somehow she figured it all out. She worked menial jobs and posed nude for photography students to survive before getting Seymour Stein to sign her for $15,000 in 1982. In 1985, when confronted about those leaked artsy nude photos (see above), she shrugged and said she did what she had to do to survive before Sire Records came along.

 

30: NOT FORCING JIMMY IOVINE TO SIGN HER DAUGHTER TO INTERSCOPE
And if Madonna can make her own way, so can her kid, Lourdes.

 

29: INTRODUCED HIP-HOP TO A YOUNG CAPTIVE AUDIENCE
gaultierEven though she really wanted RUN-D.M.C. as the opener on her Virgin Tour and got the Beastie Boys instead, Madonna was intent on introducing raw New York hip-hop to a young, impressional audience (mostly white suburban teenage girls) who would never be exposed to the burgeoning scene any other way. The Beasties were famously booed off the stage every night, but Ad-Rock, Mike D, and Madonna have all said it was one of the most important tours of their careers.

 

28: BEING CHRISTOPHER CICCONE'S SISTER

He seems difficult.

 

27: MASTURBATING WITH THE PUERTO RICAN FLAGOn October 26, 1993, Madonna masturbated with a Puerto Rican flag in front of 26,000 locals at the Juan Ramon Loubriel Stadium, in Bayamon, Puerto Rico (as evident in the Zapruder-like footage shown above). The Puerto Rican House of Representatives charged Madonna with desecration of the flag and passed a resolution to condemn her, but the only thing the incident proved was that people put way too much importance in nationalistic symbols like flags.

 

26:EMBRACING TIKTOK

Is that amyl nitrite?

 

25: SURVIVING SEAN PENN
On January 5, 1989, after putting up with his mental and physical abuse for four years, Madonna filed for divorce from Sean Penn. They both deny it now, but going off the physical evidence in the initial police report, Penn really gave Ike Turner a run for his money. Their short, disastrous relationship should get a 12-episode limited Netflix series with a reimagined Tarantino-esque Burning Bed ending.

 

24: ALL FOUR TIMES SHE HAS TURNED DOWN A STAR ON THE HOLLYWOOD WALK OF FAME
A hollow honor and she knows it.

 

23: BANNED FROM HAMILTON
hamilton
And who could blame her? Hamilton was as boring as it was thirsty and incredibly pretentious. (I dozed off twice.) Lin Manuel airing his dirty laundry out on Twitter only made him look like the asshole.

 

22: DUPING PEPSI OUT OF $5 MILLION AND CALLING OUT THE KKK IN ONE FELL SWOOP
Pepsi approached Madonna in 1989 with the same deal they offered David Bowie two years earlier: “Let us use one of your songs in our next commercial and bankroll your next world tour, plus here’s an additional $5 million for your troubles.” Bowie reworked “Modern Love” with Tina Turner, but when things got too hot to handle with his rape charge during the Glass Spider tour, Pepsi nixed the deal. Like Bowie with “Modern Love,” Madonna made a Pepsi commercial, which incorporated “Like a Prayer” for regular broadcasting. Unlike Bowie, she also made an alternate version of the video for MTV, which put a spotlight on the KKK and racism in America. After the usual conservative Christian activists threatened to boycott Pepsi and its subsidiaries (which included KFC, Taco Bell, and Pizza Hut), the contract was quietly dissolved and Madonna got to keep the bag.

 

21: BLAMING THAT BRITISH ACCENT ON GUY RITCHIE

From the stage of the London Palladium during her Madame X tour in 2020, Madonna told her audience that the cringy British accent she adopted from 1995 to 2008 was all Guy Ritchie’s fault. She didn’t get into particulars as to how it was his fault even though she started talking like an 19th century chimney sweep from Whitechapel well before she met him, but anytime you can blame an ex on your pretentious past, take the shot.

 

20: DATING JOHN JOHN 
While her divorce from Penn was pending, Madonna dated John F. Kennedy Jr. on the sly while he was publically with Christina Haag. The clandestine couple were young, they were red hot, they were magic, but we weren’t ready for them and they weren’t built to last – the fiery affair only lasted six months. But even if they were able to make it work, Jackie O. would never sign off on the relationship as she thought Madonna was crass – “not Camalot material.”

 

19: THAT THING SHE DID WITH THE AUTOMATIC HAND-DRYER IN DESPERATELY SEEKING SUSAN

Put armpit fetishism on the map.

 

18: DUMPING GUY RITCHIE'S ASS
When Madonna told her husband Guy Ritchie that she was going into pre-production for her next album, he asked her why she “had to make a new album.” Can you handle his audacity? Would she ever ask him if he had to make another film stuffed with kinetic slo-mo action shots and obscure British references? Imagine your spouse nagging you about why you “had to'' do anything you enjoyed, were good at, and made money from. Fucking preposterous.

17: FALLING AT THE BRIT AWARDS

Although the BRIT Awards academy recently (and unnecessarily) went on record stating that Madonna’s fall – an accident, mind you – at the 2015 BRITs was the most embarrassing moment of the award show’s history, they failed to recognize the evening Robbie Williams shamelessly challenged Liam Gallagher to a public boxing match from the stage of the 2001 BRITs. It was undignified. Williams has since tried to reignite the feud in 2010, 2011, and 2013, but Gallagher has yet to take the bait. Don’t look back in anger, Robbie.

 

16: NOT BEING COVERED IN TATTOOS

Refreshing!

 

15: CALLING KEVIN COSTNER BORING IN TRUTH OR DARE

Yeah, “neat” is an insult.

 

14: FALLING OVER AT A FANCY LONDON ART GALLERY OPENING
If Madonna wants to have a few glasses of wine at the opening of an art exhibit for Mert Alas and Marcus Piggot at a posh London gallery in a sexy Moschino outfit, that’s what’s gonna happen.

 

13: THIS JAPANESE SAKI COMMERCIAL

Slay, literally!

 

12: TURNING DOWN PRINCE'S OFFER TO CO-STAR IN GRAFFITI BRIDGE
Did you see it? What a disaster. Career suicide for everyone involved. Even Prince never fully recovered.

 

11: COMPLETELY BANKROLLED THAT PEDIATRIC SURGERY CENTER in Malawi
Where does she find the time for so much altruism?

 

10: HER CAMEO IN DIE ANOTHER DAY

A missed opportunity by the Broccoli family for not giving her a Bond Girl role.

 

9: PULLING THE PLUG ON HER BIOPIC
The smartest career move she’s ever made since macking on Britney at the 2003 MTV VMAs.

 

8: MACKING ON BRITNEY AT THE 2003 VMA'S
britney
As important a moment in television broadcasting history as Neil Armstrong setting foot on the moon, discovering who shot J.R, and the live documentation of the crumbling of the Berlin Wall. 

 

7: BRINGING JUSTIN TIMBERLAKE DOWN A NOTCH OR TWO
It’s called comeuppance, motherfucker.

 

6: BODY OF EVIDENCE

It wasn’t that bad!

 

5: THE SEX BOOK
sexA bold post-feminist master work!

 

4: CALLING LADY GAGA REDUCTIVE

Tea.

 

3: GOING PLATINUM WITH THOSE EYEBROWS AND PULLING IT OFF
eyebrows
Who does that?

 

2: GRACIOUSLY ALLOWING COURTNEY LOVE TO HANG HERSELF ON LIVE TELEVISION

Like watching a slow-motion car crash…

 

1: OPENING THE INAUGURAL 1984 MTV VIDEO AWARDS WITH THIS PERFORMANCE

The lack of choreography, the tousled ‘I just had rigorous sex in my dressing room’ hair, the upskirt camera angles, and lack of any reaction shots of the audience made this performance seem like MTV aired her dress rehearsal, but this is it – Generation X’s “Beatles on the Ed Sullivan Show” moment. On September 14, 1984, Madonna opened MTV’s inaugural Video Music Awards ceremony with "Like a Virgin.” She already had some success with her self-titled debut which was released a year earlier, but these three-and-a-half minutes transformed her from a lightweight, fly-by-night dance act, to instantly claiming her spot in between Prince and Michael Jackson as one of pop music’s “Big 3.” The juxtaposition of her virginal white wedding dress and the ‘Boy Toy’ belt buckle along with the provocative performance angered the right people, and while everyone over thirty predicted that it would ruin her career, the night marked one of those rare occasions where the world witnessed a star being born.


Essential Info
Photos: Wikipedia Commons
Madonna’s
Celebration Tour begins on July 15, 2023 through January 8, 2024.
Listen to
Madonna's 40 best songs here.
I'm H&M Heaven - Madonna designs for H&M in Outsideleft (2007)

Alarcon
Founder / Managing Editor

Alarcon co-founded outsideleft with lamontpaul (the Tony Wilson to his Rob Gretton) in 2004. His work for OL has attracted the attention of hundreds of thousands of readers, oh and probably the FBI, too.


about Alarcon »»

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