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Madonna's Most Head-Turning Moments Since The '90s
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00:00Pop legend Madonna has shocked the world time and time again. Need a refresher? Here are just a few
00:06of Madonna's most head-turning moments from the 90s and beyond that will make Lady Gaga's
00:11shenanigans seem like child's play. From the moment Madonna greeted David Letterman on his
00:16late-night show in 1994, it was clear that the chat was going to be anything but forgettable.
00:21As People recalled, the interview drew in one of the show's biggest audiences ever and generated
00:26a lot of pearl-clutching. In addition to letting the cuss words fly, she candidly spoke about her
00:31sex life, smoked a cigar, and kicked the interview off by handing the host a pair of underwear.
00:36The profanity and the props weren't the only things that ruffled feathers.
00:40Just have a seat.
00:41Don't make me act a fool, Dave.
00:43Letterman did not exactly diffuse the situation. The host introduced the megastar by saying she'd
00:48slept with, quote, some of the biggest names in the entertainment industry, and then tried to
00:52convince her to kiss a fan in the audience. Entertainment Weekly wrote at the time,
00:57Besides, what was most off-putting about her Letterman appearance wasn't the obscenity spew
01:01that supposedly rattled Dave, but rather Madonna's adamant refusal to converse. There was no content
01:07to her dirty, ditzy blather. At the end of the interview, Madonna refused to leave the stage while
01:12still puffing on that cigar, and an audience member yelled, quote,
01:15Get off. When Spin asked about the infamous interview the following year, Madonna said,
01:20The way he introduced me was derogatory, so my whole thing was,
01:23Okay, if that's how you want to play it, you cannot beat me at this game.
01:27When pop princesses Britney Spears and Christina Aguilera joined forces with Madonna at the 2003
01:33MTV Video Music Awards, it seemed safe to assume they were going to deliver an unforgettable show.
01:38The performance, which featured Spears and Aguilera in matching, barely-there wedding dresses,
01:43and Madonna popping out of a cake in a tux, was not just unforgettable. It became one of the most
01:48iconic in VMA's history. It was all thanks to a kiss that Madonna planted on both women during
01:53the performance, which subsequently caused hysteria among the audience and viewers at home.
01:58Fans watched as Madonna brushed Spears' hair to the side before smooching the singer. On top of that,
02:03who could forget the cameraman who panned over to Spears' apparently unamused ex-boyfriend Justin
02:09Timberlake. A media firestorm erupted, much of it centered around the kiss between Spears and
02:13Madonna and not so much Extina. As NME noted, viewers only got to see Madonna kiss Aguilera for
02:19a brief second because of the quick cut to Timberlake's reaction. Chatting with Radio Andy host Andy
02:25Cohen in 2018, Extina had this to say about the Timberlake moment,
02:29but still it was just like a cheap shot."
02:32One particular scene from Madonna's 2006 Confessions tour rubbed some people the wrong way,
02:37so much so it did not make it to primetime. During the scene in question, the pop star sings her 1986
02:43hit Live to Tell while hanging from a cross and wearing a crown of thorns on her head.
02:48According to the Associated Press, a taped version of the concert was to be shown as an NBC special.
02:53However, executives decided not to show the crucifixion part of the program. As the outlet noted,
02:58a number of religious groups were offended by the use of the crucifix and threatened to boycott.
03:02While the higher-ups at NBC did not spell out why they ultimately decided to omit the imagery,
03:07it is assumed that the network did not want to spark too much controversy or bad press.
03:11In a statement obtained by the AP, Madonna insisted,
03:15"...the scene is no different than a person wearing a cross or taking up the cross,
03:18as it says in the Bible. My performance is neither anti-Christian, sacrilegious, or blasphemous."
03:24When Madonna took the stage in Puerto Rico during her Gurley Show tour in 1993,
03:29she pulled a move that upset members of the government and citizens alike.
03:32At one point during the program, the pop star rubbed the Puerto Rican flag on her crotch.
03:37And with that, she was, as her brother Christopher Ciccone wrote in Life With My Sister Madonna,
03:42condemned by the Puerto Rican House of Representatives for desecrating their flag.
03:46Whether the move was planned or not, Pedro Rossello González, who was the governor at the time,
03:51told UPI that he didn't even bother reaching out to the singer for an apology. From his perspective,
03:56doing so would have been like, quote, asking for pears from an elm tree.
04:00As reported by the AP, a group of people protested right outside one of Madonna's homes
04:05after seeing her disrespect the flag. A demonstrator named Lisa Shaparo told the outlet,
04:10"...she's known for her tasteless acts and she has no morals. But when she insulted my country,
04:15my island, my morals kicked in."
04:17It wasn't until 2015, 22 years since her flag scandal,
04:21that Madonna returned to Puerto Rico for her Rebel Heart tour.
04:25Madonna may get away with her onstage antics and provocative music videos,
04:28but she's been called out for her theater etiquette. After the pop star attended a
04:32screening for Steve McQueen's drama 12 Years a Slave at the New York Film Festival in 2013,
04:37she found herself an enemy of all Alamo Drafthouse movie theaters. The reason? Well,
04:42as Page Six reported at the time, she apparently fired off some text messages during the film.
04:47Texting during movies is a huge no-no for the company, which tweeted,
04:50"...until she apologizes to movie fans, Madonna is banned from watching movies."
04:55When Madonna attended Hamilton in 2015, word got out that she was apparently yet
04:59again buried in her phone. As The Daily News reported, show creator and star Lin-Manuel Miranda
05:05took a second during the curtain call to call out someone who was typing all throughout the show.
05:09He then tweeted about a celeb who was forbidden to come backstage after the performance because
05:14they were texting through the entirety of the second act. When Dot429 asked Hamilton actor
05:19Jonathan Groff if he was bummed about the blacklisting, he said,
05:22"...no. It was a black void of the audience in front of us, and her face there, perfectly lit
05:26by the light of her iPhone through three quarters of the show."
05:29In a statement to Us Weekly, her team denied the story.
05:33Viewers watching the 2018 MTV VMAs believed Madonna was way out of touch when she delivered what
05:39was supposed to be a dedication to the late Aretha Franklin. Instead, it wound up becoming
05:44a six-minute speech about how the Queen of Soul helped the Queen of Pop become the superstar she
05:48is today. While Madonna did add a few words about how singing Franklin's You Make Me Feel Like a
05:53Natural Woman at an audition played an instrumental role in her career, the audience was left baffled at
05:58how she was able to take a tribute to Franklin and make it about herself. Following her VMAs speech,
06:03Madonna took to her Instagram, where she clarified that she was just following MTV's request, writing,
06:09"...I was asked to present Video of the Year by MTV, and then they asked me to share my anecdotes
06:14I had in my career connected with Aretha Franklin. I did not intend to do a tribute to her. That
06:18would be impossible in two minutes with all the noise and tinsel of an award show."
06:23A day after Madonna released her 1992 Erotica record, moving away from being a material girl to
06:29introducing fans to Mistress Dita, the singer debuted a coffee table book titled Sex. With her newly
06:35released album and a book filled with photographs of herself in erotic poses, as well as cameos by
06:40Vanilla Ice and Naomi Campbell, the singer sure gave people something to talk about.
06:44Madge had already made enemies with the Vatican, religious groups, and parents because of her
06:48song Papa Don't Preach and her music video for Justify My Love. Even MTV banned the latter from
06:54airing. The book received mixed reviews, with the New York Times stating,
06:58"...Of course, some of us actually like the opposite sex. Some of us believe it is possible
07:02to have great sex without whips, third parties, or domestic pets. Maybe sex can be a warning about
07:08what happens when pop icons become bloated one way or another."
07:11Backlash be darned, however, the book was a hit. According to Rolling Stone,
07:15a limited 1.5 million copies sold out right away.
07:19Couples who are together for some time are bound to pick up on each other's habits,
07:23but Madonna took things one step further when she took on her second husband's accent.
07:28Madge and Englishman Guy Ritchie split in 2008 after eight years of marriage,
07:32but not before the very American star took on a British-esque manner of speaking.
07:36The singer said at a 2020 concert,
07:39"...I didn't know what anyone was talking about until I heard old interviews of myself.
07:43And then I was horrified and flabbergasted. Why did you let me do that to myself? I'm from
07:47Michigan. It's all Guy Ritchie's fault."
07:49But was the Snatch director really all to blame? As Entertainment Weekly reported,
07:53fans noticed Madonna was using a bizarre British accent all the way back in 1995,
07:58and again a few years later. A spokeswoman for Madonna told EW that the star tends to drop in
08:03and out of accents depending on what movie she happens to be working on at the time,
08:07or who she happens to be working with at the time.
08:10Madonna's 2015 Rebel Hearts cover art showed the singer's face entangled in a black cord,
08:15but when she edited the faces of iconic leaders,
08:17it caused an uproar with people taking to social media to condemn her actions.
08:21According to HuffPost, Madonna began sharing images on Twitter of several famous figures
08:26like Martin Luther King Jr., Nelson Mandela, and Jesus Christ, all of which were altered
08:31to resemble her album cover. Madonna wrote alongside the MLK image,
08:35This hashtag rebel heart had a dream.
08:38This art project to promote her new album faced a ton of backlash. Billboard reported that people
08:43found the pictures insensitive, while others believed it was her way to express her creativity.
08:48Art is important in our lives. I don't think people emphasize that enough."
08:54However, throughout her promotion, she had also altered the faces of stars like Miley Cyrus,
08:58Lady Gaga, and even Homer Simpson. Acknowledging those who believed she was
09:02in the wrong for her doctored photos, Madonna tweeted,
09:05"'Dear haters, I have so much more for you to be mad at. Be patient.'"
09:09Not unlike her music, Madonna's dating history has turned heads. She's been linked to actors like
09:14Sean Penn, had a brief romance with Dennis Rodman, and may or may not have had a fling with former
09:19baseball player Alex Rodriguez. After her marriage to director Guy Ritchie fell apart in 2008,
09:24it appeared that Madonna had set her sights on dating men much younger than her.
09:28In 2009, Madonna, who was 50 at the time, was in a thing with a 22-year-old model by the name of
09:34Jésus-Louche. After they split, the singer met a French dancer and, quote,
09:38toy boy named Brahim Zaiba in 2011, but they broke up in 2013. By the next year,
09:44Madonna was spotted with personal trainer Timur Stephens, who was 26 years old when they got
09:50together, but that relationship also fizzled out, per Us Weekly. Madonna was going to give love one
09:55more try when she started dating a 25-year-old dancer named Ala Malik Williams in 2019, per Page Six.
10:01As of November 2021, the couple is still going strong, with Page Six reporting that they
10:06trekked out to Italy in August 2021 to celebrate Madonna's 63rd birthday. Along with the pair were
10:12the singer's children, Lourdes and Rocco, who are very close in age to Williams.
10:17Interestingly, Madonna once shared to ABC News that she didn't, quote,
10:20choose to date younger men, adding,
10:22"...I've never really lived a conventional life."
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