A star from the very beginning.©Getty Images
Britney Spears is an icon, full stop. From her meteoric rise to fame to her dazzling music videos and performances to her best-selling book, she’s had a prolific life and career. Much of her life between 2008 and 2023 was controlled via a conservatorship, but thanks to her 2023 memoir The Woman In Me, in which Spears detailed how her life was controlled by people she had mistakenly trusted, we finally know Spears’ side of the story.
But any Spears fan—including us at Marie Claire—will tell you that the beloved superstar is much more than her struggles. From her joyful, can’t-look-away performance style to her inimitable vocals to her career choices, Spears has proven time and time again to be both timeless and resilient. The fact that her career has spanned so many decades, in spite of what she privately endured, is a testament to that. Below, the most iconic Britney Spears moments of all time.
Making Her Own Perfume, 2000s
Technically, Spears made more than one fragrance. But back in the day, there were fewer clear signs of success than making a cute-smelling scent in an adorable pink bottle for teens to buy (I admit: I bought it and I liked it). Her first fragrance, Curious, was re-introduced to fans and sold as a bundle with her memoir, The Woman in Me, starting in October 2023, so apparently she brought back her most notable, popular scent for excited fans.
Hosting ‘SNL’ in 2002
The first time Saturday Night Live had Spears on as a host and musical guest in 2000, she was only 18(!). Few hosts have been younger than her—the Olsen twins at 17, Fred Savage at 13, and Drew Barrymore at 7(!!) being notable examples. 2000 was an important year for spears, with “Oops!…I Did It Again” just about to be released. She returned again in 2002 as a host and musical guest; The show played with her bombshell persona, including this skit as Barbie’s sister Skipper.
‘SNL’ (2003)
In 2003, Spears came to Saturday Night Live as a musical guest (after hosting in 2000 and 2002). She delivered a gorgeous rendition of “Everytime,” which had been rumored to be about her relationship with ex Justin Timberlake. Considering that Timberlake had also written some very public songs about their relationship, it was all the sadder.
A Cameo in ‘Sabrina the Teenage Witch,’ 1999
My personal favorite ’90s TV show, Sabrina the Teenage Witch was a huge cultural touchstone for a ton of teens. So this cameo, which Spears did in 1999 as she was becoming a household name, was an important part of raising her profile (she performed as herself, of course). Melissa Joan Hart and Spears were contemporaries and crossing paths a lot at the time—the two became friendly, and Hart would later cameo in Spear’s music video “Drive Me Crazy,” featured on the soundtrack for Hart’s movie of the same name.
Performing at the Grammys, 2000
A first-time nominee that year, Spears also took to the stage to deliver a riveting performance. We started with young Spears watching the Grammys as a child and envisioning herself being there one day, which then transitions to “From the Bottom of My Broken Heart” (a power ballad) and a remix of the classic “…Baby One More Time” with some amazing dance moves and a cadre of backup dancers, including…robots! It was an impressive feat for the young starlet.
Kicking Butt in Vegas
Spears’ residency in Vegas was wildly popular, but—as she revealed in the court case to terminate her conservatorship and later in her memoir—she didn’t want to participate. She said she found creative ways to rebel against the control over her, including dancing in such a way so as not to move her hair (which would be a sign of enthusiasm) and not giving her all to the dance moves. She also said it hurt her spirit not to give it her all. But her fans came out to support her (the show won the best of Las Vegas award in 2015 and 2017), and the show grossed nearly $140 million.
Doing a ‘Glee’ Cameo, 2010
In the ’00s (after her reality show Chaotic), Spears appeared on some of the most popular shows of the day. Glee, which dipped into the pop star’s archive more than once, was an intuitive fit for Spears. According to creator Ryan Murphy, the cast, some of whom grew up wanting to be like Spears, were absolutely awed. “It was literally like the President had come,” Murphy told E!. “We all had to wear wristbands. I couldn’t get into my own sets at one point, which I thought was hilarious.”
Doing a ‘How I Met Your Mother’ Cameo, 2008
In How I Met Your Mother‘s third season, Spears cameoed as receptionist Abby—Ted’s at a dermatologist’s office to get a tattoo removed and is attracted to his doctor, but instead grabs Abby’s attention. He remains oblivious, and she instead briefly gets together with Barney. Apparently Spears was a fan of the show and actually asked to be on it—obviously, the stunt casting boosted ratings for the show, and the whole cast was impressed by her comedic chops.
Doing a ‘Will and Grace’ Cameo, 2006
Often considered one of Spears’ funniest TV cameos, the red dress, bandana-wearing, conservative Amber-Louise takes over Jack’s talk show with lines like, “If you question our president, then you’re a dirty traitor” but is secretly a lesbian called Peg. Playing so deliciously against type is one of the secrets to her success—the bigger the role, the harder she leans in.
Winning Awards at the VMAs, 2008
In 2007, Spears had performed “Gimme More” at the VMAs. It was supposed to be a comeback, but the visibly nervous singer was shaky. She admitted later that she was dealing with postpartum struggles and was pressured by her team to perform. In 2008, when she got onstage at that same awards ceremony to accept her first Moonman award, she looked healthier and happier. Fans were hopeful that she was doing better than she had been.
