Don’t Call It a Comeback, 2008
At the 2003 VMAs, Spears won Video of the Year, Best Female Video, and Best Pop Video (all for the song “Piece of Me”)—marking a return to the spotlight for the singer. Spears’ personal life would continue to be tumultuous during this time (as she noted in her memoir, she was dealing with postpartum depression and unsupportive people in her life) but she remained just as beloved for her work. People were clearly rooting for her, and continued to root for her.
Iconic Magazine Covers
Over the years, Spears graced the covers of a multitude of magazines. There are many iconic ones, but this cover for W Magazine was an important one. Breaking her silence after her breakup with Timberlake, Spears got candid about being intimate with her boyfriend (there was a lot of talk about Spears’ romantic life and history in the ’00s, unfortunately) and called the breakup the most painful thing she’d ever been through. It was an important part of reclaiming her narrative.
‘Rolling Stone’ Covers
For a singer, there was no more impressive feat than getting on the cover of Rolling Stone—and Britney Spears had eight (seven were solo, one was with other iconic female singers). The first was in 1999 when she was 17 and was controversial even for the time. Her last was in 2008, announcing her comeback. Throughout, Spears tried to be as candid and genuine as possible in her interviews.
Filming THAT Pepsi Commercial, 2003
Also known as the “‘We Will Rock You’ commercial,” Spears, Pink, and Beyoncé play gladiators who, instead of fighting each other, sing “We Will Rock You” and drink Pepsi (lol). Spears and Bey had been spokespeople for the brand previous to this, but the commercial instantly became one of the most iconic the Super Bowl has ever seen. Pink later said of the experience, “I’m very protective of [Britney], and she’s the sweetest person in the world.”
Performing Onstage at the Super Bowl, 2001
The “Kings of Rock and Pop,” Aerosmith and *NSYNC, were onstage performing together for the Super Bowl Halftime Performance. And then. Spears, Mary J. Blige, and Nelly all took to the stage so they could all sing “Walk This Way.” Spears and Timberlake (who were dating at the time) even walked together a few steps, giving us a look at their performance chemistry. At the time, the show made a name for bringing in surprises, but this was probably the biggest surprise of them all.
Kissing Madonna at the 2003 VMAs
Three icons performing onstage together was enough to excite a lot of fans—and then Madonna kissed both Spears and Aguilera live on stage, which broke just about everyone’s brains. Unfortunately, a lot of backlash (much of it aimed at Spears) resulted from the incident—including frustration from Aguilera, whose kiss with Madonna was mostly ignored so the producers could cut away to Spears’ then-boyfriend Timberlake’s upset reaction. Calling it a “cheap shot,” Aguilera said in a 2018 Radio Andy interview, “I definitely saw the newspaper the next day. It was like, ‘Oh, well, I guess I got left out of that one.'”
Hosting With Xtina at the 2000 MTV Video Music Awards
The media made a lot of the fact that Christina Aguilera and Spears were both stars who came out of The All-New Mickey Mouse Club, and the two were often pitted against each other in troubling ways. So this obviously engineered appearance, in which they bantered and introduced Whitney Houston together at the VMAs, made fans intensely excited. (The two singers would go on to have a fairly public feud in the ’00s, but would later reconcile and express love for each other.)
Performing at the 2000 MTV Video Music Awards
One of the most well-remembered VMA performances of all time, Spears (performing in a suit that she ripped off to reveal a sheer bodysuit) sang live and did some unbelievably intense choreography. Beginning with her sitting astride a chair, then descending the stairs doing a live version of the song “Satisfaction,” then launching into a killer remixed version of “Oops!…I Did It Again,” it was an instantly icon-making performance.
Many, Many Iconic Music Videos
This is a still from one of Spears’ early singles, “Sometimes” (gotta love the very ’90s, all-white matching fashion!). But one of Spears’ most impressive career moves was to create music videos that shocked, delighted, and wowed audiences just as much as the songs. Most notably, her “Toxic” music video (in which she plays a spy who scales a building, poisons a guy, and pretends to be a sexy flight attendant), and her “Oops!…I Did It Again” music video (in which she dons red latex and plays a Martian and flirts with an astronaut) were instant fan-faves.
The ‘Snake Moment’ at the 2001 MTV Music Awards
At the time, Spears performing with an honest-to-goodness, real, live snake at the VMAs was wild enough (and instantly made her known as a fearless performer). But in her memoir The Woman in Me, she admitted that the moment was terrifying. “All I knew was to look down, because I felt if I looked up and caught its eye, it would kill me…In my head I was saying, Just perform, just use your legs and perform. But what nobody knows is that as I was singing, the snake brought its head right around to my face, right up to me, and started hissing.”
Performing ‘…Baby One More Time’ in 1999
One of Spears’ talents is her ability to go 100 percent on her dance moves (until she would go on to have knee injuries later in her career). After her first song came out and instantly became a success, people flocked to see her perform—and were not disappointed. Spears would go on to be known for her energetic performances and shows, but even in the beginning she had a unique look and a high-energy style that begged you to dance along.
