Madonna's Most Head-Turning Moments Since The '90s

Many Hollywood stars love to cross the line of conformity and embrace a shocking moment. Take Lady Gaga, for example. Though she has been celebrated for her work, Stefani Germanotta has also been in the limelight for her wild fashion choices and outrageous stunts. Remember when she rocked literal cuts of meat at the 2010 VMAs? Or her various red carpet entrances that included hatching from an egg to arriving on a human horse? Lady Gaga has never been afraid of experimentation and has even been likened to Madonna. However, when comparing both women's most bizarre and head-turning moments, there's one clear winner.

Her Madgesty has been stirring up controversy since she made her debut in the '80s. For starters, her music video for "Like a Prayer" was condemned by the Vatican, and the clip for "Justify My Love" was infamously cut from MTV for its racy scenes (which are pretty tame by today's standards). Her onstage antics prompted religious groups to protest outside her concerts, and she even made a few government officials angry. Even her talk show appearances have been dubbed wacky and uncomfortable, but hey, there is no one like Madge.

Here are just a few of Madonna's most head-turning moments from the '90s and beyond that will make any reader think Lady Gaga's shenanigans were mere child's play.

Madonna made waves on David Letterman

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. Letterman did not exactly diffuse the situation: The host introduced the megastar by saying she'd slept with "some of the biggest names in the entertainment industry" and then tried to convince her to kiss a fan in the audience. 

The profanity and the props weren't the only things that ruffled feathers. "Besides, what was most offputting about her 'Letterman' appearance wasn't the obscenity spew that supposedly rattled Dave," Entertainment Weekly wrote at the time, "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, "Get off!" Letterman later joked, "Coming up in the next half hour, Mother Teresa is going to drop by!"

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."

The VMAs moment that rocked the world

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, subsequently causing hysteria among the audience and viewers at home. Fans watched as Madonna brushed Spears' hair to the side and smooch 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 said the Timberlake moment was "a cheap shot," adding that she felt "left out" of all the buzz. That said, she told Zane Lowe (via E! News) in 2020 that as far as she's concerned, the kiss really "wasn't shocking."

Madonna got up on a cross

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. In the scene in question, the pop star sings her 1986 hit "Live to Tell" while hanging from a cross and with a crown of thorns on her head. According to the AP (via The Hollywood Reporter), 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 (via The Washington Post), Madonna insisted the scene was "not a mocking of the church" and was "no different than a person wearing a cross or 'taking up the cross' as it says in the Bible." She continued, "My performance is neither anti-Christian, sacrilegious or blasphemous." Interestingly, before the display got the chop from the broadcast, the then-president of NBC Entertainment Kevin Reilly told TVGuide that the network "didn't see it as being ultimately inappropriate."

Drake was thrown for a loop at Coachella

Madonna knows how to keep audiences and collaborators guessing. When she performed with Drake at Coachella in 2015, she surprised not only fans but the rapper himself when she kissed him onstage. And we don't mean a quick smackeroo, a la the ones she planted on Britney Spears and Christina Aguilera at the 2003 MTV VMAs. The "Material Girl" singer had a full-on make-out session with Drake that apparently threw him for a loop.

After the surprise kiss, Drake grabbed his mouth and reacted in a way that suggested he might be, as ABC News put it, "in agony or disgust, pain or confusion," and went on to ask the crowd, "What the f*** just happened?" However, the rapper had to clarify to his fans on Instagram that his reaction wasn't a negative one. "Don't misinterpret my shock!!" he wrote. "I got to make out with the queen Madonna." 

A source told TMZ later that Drake apparently was not a fan of whatever lipstick Madonna was wearing which was the reason for his visceral response. "Drake said he wasn't disgusted by the kiss, he actually loved it," the tipster dished. "He said he was disgusted by the after-taste of her lipstick." He couldn't get over that lip stain, it left its mark on him. (But he probably doesn't want the lipstick's hot love or emotion endlessly.)

Madonna sparked fury with a Photoshop job

Who knew that Madonna was also proficient in Photoshop? In 2018, the songstress took it upon herself to edit her album covers into a still shot from Beyonce and Jay-Z's music video for "Apes**t." In the doctored photo, which Madonna posted on Instagram, Bey and Jay-Z gaze up at covers for "Ray of Light," "Rebel Heart," and "True Blue" instead of the centuries-old works of art on display in the iconic museum. Per Complex, the caption originally read, "Learning from the #art #equals #freedom," but she removed the word "master" after being called out for using it in this context. (She did not take down the tweet with the original caption.) As VH1 noted, Queen Bey's fandom, the Beyhive, wasted no time in calling out the "Evita" star on social media for the post. 

Beyonce and Jay-Z have never publicly addressed the Photoshopped image, but Bey has spoken about Madonna in the past. According to The Hollywood Reporter, after the "Love On Top" singer stunned the planet with the surprise release of her self-titled visual album in 2013, she told attendees at a private screening, "I felt like I wanted to follow the footsteps of Madonna and be a powerhouse and have my own empire and show other women when you get to this point in your career, you don't have to go sign with someone else and share your money and your success — you do it yourself."

Madonna outraged Puerto Rico with flag stunt

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, believing it would be like "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, per Latin Post.

The songstress was banned from theaters

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 songstress 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 Entertainment Weekly asked CEO Tim League about this ban, he said, "Yeah, I'm serious, but I don't think it really affects her life that much."

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, and then tweeted about a celeb "who was texting all through Act 2" and was not permitted to come backstage after the performance. When Dot429 (via Vulture) 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.

She used a slur in an Instagram caption

In 2015, Madonna posted a photo of her son Rocco Ritchie in a boxing ring. Seems harmless enough, right? Eh, nope. Per Rolling Stone, the singer used the n-word in her caption, and, understandably, it was a big problem. Initially, she tried to shrug off the criticism, editing her caption to read: "Ok let me start again. #get off my d*** haters."

It took some time for Madonna to realize that, as a white woman, using that word was not okay in any shape or form, and she issued an apology on social media. In a since-deleted Instagram post (via Rolling Stone), she said, "It was not meant to be a racial slur.. I am not racist. There's no way to defend the use of the word. It was all about intention. ... it was used as a term of endearment toward my son who is white. I appreciate that it's a provocative word and I apologize if it gave people the wrong impression. Forgive me."

After the backlash, Madonna ended up taking the photo down from her Instagram and wrote (via Rolling Stone), "MY job is to inspire and bring people together ... The last thing I want to do is bring chaos or cause separation in any way."

The tribute to Aretha Franklin that didn't land

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, but ended 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 and thanked the late icon for "empowering all of us," the audience was left baffled at how Madonna 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. "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!" she wrote. "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 ... Unfortunately most people have short attention spans, and are so quick to judge."

Madonna published a head-turning book

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 the coffee table book "Sex."

With her newly released album and a book filled with photographs of Madonna 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 with her song "Papa Don't Preach" and her music video for "Justify My Love — even MTV banned the latter from airing. Heck, why not put out a book filled with pornographic imagery, too?

The tome 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," adding, "Maybe 'Sex' can be a warning about what happens when pop icons become bloated, one way or another." Meanwhile, The Guardian wrote that the book "should be applauded for its balls-to-the-walls honesty." Backlash be darned, the book was a hit: According to Rolling Stone, a limited 1.5 million copies sold out right away.

Remember her British accent?

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. "I didn't know what anyone was talking about until I heard old interviews of myself," she said at a 2020 concert (via BBC). "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-ish 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. "When Madonna had a Southern assistant, she was talking with a Southern accent," the rep told the outlet. "In regard to the movie ['The Next Best Thing'], it's probably because she was with Rupert [Everett] so much." 

Whether or not the accent was a result of marrying a British man, Madonna's cringey "British" accent sure made some memorable cameos in a lot of interviews. 

Madonna doctored photos of famous leaders

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. Per HuffPost, Madonna began sharing altered images on Twitter of several famous figures like Martin Luther King Jr., Nelson Mandela, and Jesus Christ to look like her album cover. "This #rebelheart had a dream," she wrote alongside the MLK image, while Mandela's read, "This #rebelheart fought for freedom." She even dubbed Jesus "One of the first #rebelhearts."

Her "art project" to promote her new album faced a ton of backlash with Billboard reporting that people found the pictures "insensitive" while others believed it was her way to express her creativity. 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!"

Another tour, more controversial imagery

During the "Nobody Knows Me" segment of Madonna's 2012 MDNA tour, a controversy-generating video played in the background. In one of the clip's most talked-about moments, there was a swastika superimposed on the forehead of French politician Marine Le Pen. The tour, which kicked off in Tel Aviv, Israel, also featured images of Hu Jintao, Sarah Palin, and Adolf Hitler, which came right after Le Pen, per The New York Times.

In response, The Guardian reported that France's far-right party National Front declared that they would sue the singer if the image was not removed. "If she tries that in France, we'll see what happens. It's understandable when aging singers who need publicity go to such extremes," Le Pen said in a statement. While Madonna continued to use the image throughout her tour, the Daily Beast reported that she had finally removed the swastika and instead, had a question mark superimposed on Le Pen's forehead while performing in Nice, France. 

As for Madonna's reasoning behind the imagery, she told a Brazilian television channel (via BBC), "That film that was created is about the intolerance that we human beings have for one another and how much we judge people before knowing them."

Much has been made of Madonna's love life

Not unlike her music, Madonna's dating history has turned heads. She was married to actor Sean Penn for four years, from 1985 to 1989. She had a brief romance with Dennis Rodman, dated rapper Vanilla Ice, 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 "toyboy" 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 this writing, 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 "choose to" date younger men, adding, "I've never really lived a conventional life."