Pop legend Madonna has shocked the world time and time again. Need a refresher? Here are
just a few of Madonna's most head-turning moments from the '90s and beyond that will
make Lady Gaga's shenanigans seem like child's play.
From the moment Madonna greeted David Letterman on his late-night show in 1994, it was clear
that the chat was going to be anything but forgettable. As People recalled, the interview
drew in one of the show's biggest audiences ever — and generated a lot of pearl-clutching.
In addition to letting the cuss words fly, she candidly spoke about her sex life, smoked
a cigar, and kicked the interview off by handing the host a pair of underwear. The profanity
and the props weren't the only things that ruffled feathers.
"Just have a seat."
"Don't make me act a fool, Dave."
Letterman did not exactly diffuse the situation. The host introduced the megastar by saying
she'd slept with, quote, "some of the biggest names" in the entertainment industry, and
then tried to convince her to kiss a fan in the audience. Entertainment Weekly wrote at
the time:
"Besides, what was most off-putting about her 'Letterman' appearance wasn't the obscenity
spew that supposedly rattled Dave but, rather, Madonna's adamant refusal to converse — there
was no content to her dirty, ditzy blather."
At the end of the interview, Madonna refused to leave the stage while still puffing on
that cigar, and an audience member yelled, quote, "Get off!" When Spin asked about the
infamous interview the following year, Madonna said,
"The way he 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."
When pop princesses Britney Spears and Christina Aguilera joined forces with Madonna at the
2003 MTV Video Music Awards, it seemed safe to assume they were going to deliver an unforgettable
show. The performance — which featured Spears and Aguilera in matching barely-there wedding
dresses and Madonna popping out of a cake in a tux — was not just unforgettable. It
became one of the most iconic in VMAs history.
It was all thanks to a kiss that Madonna planted on both women during the performance, which
subsequently caused hysteria among the audience and viewers at home. Fans watched as Madonna
brushed Spears' hair to the side before smooching the singer. On top of that, who could forget
the cameraman who panned over to Spears' apparently unamused ex-boyfriend Justin Timberlake?
A media firestorm erupted, with much of it centered around the kiss between Spears and
Madonna and not so much Xtina. As NME noted, viewers only got to see Madonna kiss Aguilera
for a brief second because of the quick cut to Timberlake's reaction. Chatting with "Radio
Andy" host Andy Cohen in 2018, Xtina had this to say about the Timberlake moment:
"But still it was just like a, a cheap shot."
One particular scene from Madonna's 2006 "Confessions" tour rubbed some people the wrong way — so
much so, it did not make it to primetime. During the scene in question, the pop star
sings her 1986 hit "Live to Tell" while hanging from a cross and wearing a crown of thorns
on her head. According to the Associated Press, a taped version of the concert was to be shown
as an NBC special, however, executives decided to not show the crucifixion part of the program.
As the outlet noted, a number of religious groups were offended by the use of the crucifix
and threatened a boycott. While the higher-ups at NBC did not spell out why they ultimately
decided to omit the imagery, it is assumed the network did not want to spark too much
controversy or bad press. In a statement obtained by the AP, Madonna insisted:
"[The scene is] no different than a person wearing a cross or 'taking up the cross' as
it says in the Bible. My performance is neither anti-Christian, sacrilegious or blasphemous."
When Madonna took the stage in Puerto Rico during her "Girlie Show" tour in 1993, she
pulled a move that upset members of the government and citizens alike. At one point during the
program, the pop star rubbed the Puerto Rican flag on her crotch. And with that, she was,
as her brother Christopher Ciccone wrote in Life with My Sister Madonna,
"condemned by the Puerto Rican House of Representatives for desecrating their flag."
Whether the move was planned or not, Pedro Rossello Gonzalez, who was the governor at
the time, told UPI that he didn't even bother reaching out to the singer for an apology.
From his perspective, doing so would have been like, quote, "asking for pears from an
elm tree." As reported by the AP, a group of people protested right outside one of Madonna's
homes after seeing her disrespect the flag. A demonstrator named Lisa Chaparro told the
outlet "She's known for her tasteless acts and she
has no morals. But when she insulted my country, my island, my morals kicked in."
It wasn't until 2015 — 22 years since her flag scandal — that Madonna returned to
Puerto Rico for her Rebel Heart tour.
Madonna may get away with her on-stage antics and provocative music videos, but she's been
called out for her theater etiquette. After the pop star attended a screening for Steve
McQueen's drama 12 Years A Slave at the New York Film Festival in 2013, she found herself
an enemy of all Alamo Drafthouse movie theaters. The reason? Well, as Page Six reported at
the time, she apparently fired off some text messages during the film. Texting during movies
is a huge no-no for the company, which tweeted,
"Until she apologizes to movie fans, Madonna is banned from watching movies."
When Madonna attended Hamilton in 2015, word got out that she was apparently yet again
buried in her phone. As the Daily News reported, show creator and star Lin-Manuel Miranda took
a second during the curtain call to call out someone who was typing all throughout the
show. He then tweeted about a celeb who was forbidden to come backstage after the performance
because they were texting through the entirety of the second act. When Dot429 asked Hamilton
actor Jonathan Groff if he was bummed about the blacklisting, he said,
"No. [...] It was a black void of the audience in front of us and her face there perfectly
lit by the light of her iPhone through three-quarters of the show."
In a statement to Us Weekly, her team denied the story.
Viewers watching the 2018 MTV VMAs believed Madonna was way out of touch when she delivered
what was supposed to be a dedication to the late Aretha Franklin. Instead, it wound up
becoming a six-minute speech about how the Queen of Soul helped the Queen of Pop become
the superstar she is today. While Madonna did add a few words about how singing Franklin's
"(You Make Me Feel Like) A Natural Woman" at an audition played an instrumental role
in her career, the audience was left baffled at how she was able to take a tribute to Franklin
and make it about herself.
Following her VMAs speech, Madonna took to her Instagram where she clarified that she
was just following MTV's request, writing:
"I was asked to present video of the year by MTV! And then they asked me to share my
anecdotes[.] I had in my career connected with Aretha Franklin! I did not intend to
do a tribute to her! That would be impossible in 2 minutes with all the noise and tinsel
of an award show [...]"
A day after Madonna released her 1992 Erotica record — moving away from being a "Material
Girl" to introducing fans to "Mistress Dita" — the singer debuted a coffee table book
titled Sex. With her newly released album and a book filled with photographs of herself
in erotic poses, as well as cameos by Vanilla Ice and Naomi Campbell, the singer sure gave
people something to talk about.
Madge had already made enemies with the Vatican, religious groups, and parents because of her
song "Papa Don't Preach" and her music video for "Justify My Love" — even MTV banned
the latter from airing. The book received mixed reviews, with The New York Times stating,
"Of course, some of us actually like the opposite sex; some of us believe it is possible to
have great sex without whips, third parties, or domestic pets. Maybe 'Sex' can be a warning
about what happens when pop icons become bloated, one way or another."
Backlash be darned, however, the book was a hit. According to Rolling Stone, a limited
1.5 million copies sold out right away.
Couples who are together for some time are bound to pick up on each other's habits, but
Madonna took things one step further when she took on her second husband's accent. Madge
and Englishman Guy Ritchie split in 2008 after eight years of marriage, but not before the
very American star took on a British-esque manner of speaking. The singer said at a 2020
concert:
"I didn't know what anyone was talking about until I heard old interviews of myself. And
then I was horrified and flabbergasted. Why did you let me do that to myself? I'm from
Michigan! It's all Guy Ritchie's fault."
But was the Snatch director really all to blame? As Entertainment Weekly reported, fans
noticed Madonna was using a bizarre British accent all the way back in 1995 and again
a few years later. A spokeswoman for Madonna told EW that the star tends to drop in and
out of accents depending on what movie she happens to be working on at the time or who
she happens to be working with at the time.
Madonna's 2015 Rebel Hearts cover art showed the singer's face entangled in a black cord.
But when she edited the faces of iconic leaders, it caused an uproar, with people taking to
social media to condemn her actions. According to HuffPost, Madonna began sharing images
on Twitter of several famous figures like Martin Luther King Jr., Nelson Mandela, and
Jesus Christ, all of which were altered to resemble her album cover. Madonna wrote alongside
the MLK image:
"This #rebelheart had a dream."
This "art project" to promote her new album faced a ton of backlash. Billboard reported
that people found the pictures "insensitive" while others believed it was her way to express
her creativity.
"Art is important in our lives. I don't think people emphasize that enough."
However, throughout her promotion, she had also altered the faces of stars like Miley
Cyrus, Lady Gaga, and even Homer Simpson. Acknowledging those who believed she was in
the wrong for her doctored photos, Madonna tweeted,
"Dear Haters, I have so much more for you to be mad at... Be patient!"
Not unlike her music, Madonna's dating history has turned heads. She's been linked to actors
like Sean Penn, had a brief romance with Dennis Rodman, and may or may not have had a fling
with former baseball player Alex Rodriguez. After her marriage to director Guy Ritchie
fell apart in 2008, it appeared that Madonna had set her sights on dating men much younger
than her.
In 2009, Madonna, who was 50 at the time, was in a thing with a 22-year-old model by
the name of Jesus Luz. After they split, the singer met a French dancer and, quote, "toyboy"
named Brahim Zaibat in 2011, but they broke up in 2013. By the next year, Madonna was
spotted with personal trainer Timor Steffens, who was 26 years old when they got together,
but that relationship also fizzled out, per Us Weekly.
Madonna was going to give love one more try when she started dating a 25-year-old dancer
named Ahlamalik Williams in 2019, per Page Six. As of November 2021, the couple is still
going strong, with Page Six reporting that they trekked out to Italy in August 2021 to
celebrate Madonna's 63rd birthday. Along with the pair were the singer's children, Lourdes
and Rocco, who are very close in age to Williams. Interestingly, Madonna once shared to ABC
News that she didn't, quote, "choose to" date younger men, adding,
"I've never really lived a conventional life."
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