Britney Debuts As A Naughty Schoolgirl In The "Baby, One More Time" Video
Britney put the schoolgirl uniform on the map with the release of her then-raunchy "Baby, One More Time" video. The debut single from her 1998 first album (also titled Baby, One More Time) sold over 10 million copies, thanks to that sensational video, featuring Britney grinding her way through the halls of a Catholic school. Girls wanted to tie their hair in pigtails, guys watched in awe.
Britney Receives $8 Million Pepsi Sponsorship Deal
In the early 2000s, everyone wanted a piece of Britney. Pepsi offered her an $8 million endorsement deal, resulting in two spectacular commercials (both airing during the Super Bowl). Unfortunately, the singer eventually lost her sponsorship when paparazzi photographed her several times enjoying a cool can of Coke. Too bad she couldn't switch teams.
Britney Spears – 'Crossroads' (2002)
At the peak of her pop stardom there were many people who genuinely thought that Britney Spears could one day make the leap from music to movies. Of course that was long before the Spears> much-publicised personal problems and probably prior to them seeing her star in this disappointing coming-of-age comedy from MTV.
Britney Marries Childhood Crush For 55 Hours
In 2004, Britney Spears and her childhood friend Jason Alexander (NOT the Seinfeld star) underwent what might be the ultimate Las Vegas wedding. Registered under the name "Alotta Warmheart", Spears and Alexander were married at the Little White Chapel in Vegas at five in the morning after an apparently romantic viewing of the Texas Chainsaw Massacre. While the marriage was annulled 55 hours later, Alexander told Access Hollywood, "It was just so crazy, man. We were just looking at each other and said, 'Let's do something wild, crazy. Let's go get married, just for the hell of it.'"
Britney Dates Her Fellow Mouseketeer Justin Timberlake
Justin Timberlake and Britney Spears had a beautiful three-year relationship where they successfully wore matching denim outfits to the MTV Video Music Awards, supported each other on tour and had America wondering if they would ever go all the way. While later interviews revealed that the two former Mousekeeters were definitely having a normal 20s relationship, the sexual tension they provided would ultimately be a great first love for the two pop stars.
Britney Dances With A Python At The 2001 VMAS
Britney stole the show when she performed a salacious rendition of her hit "I'm A Slave 4 U" at the 2001 MTV Video Music Awards, co-starring an albino Burmese python apparently named "Banana." All combinations sexy, crazy and cool, Britney's belly dance-inspired choreography and rocking abs turned her into a pop icon.
Britney Has Her First Girl-On-Girl Kiss WIth Madonna
It was the kiss that launched a thousand tabloids when Madonna kissed Britney Spears during an MTV VMA performance of "Hollywood" in 2003. While Madonna also made out with her rival Christina Aguilera during the same segment, eyes (including those of Britney's recent ex-boyfriend Justin Timberlake) were locked on Britney. While Britney remarked that she had "never kissed a woman before," the two would later duet in the saucy single "Me Against The Music."
Britney Spears Marries Kevin Federline
In backup dancer/aspiring rapper Kevin Federline, it seemed Britney Spears had found her down-home soulmate. While the two courted the tabloids with their white trash antics, including going shoeless in gas stations and eating McDonalds constantly, they also starred in the reality show Britney and Kevin: Chaotic. A brief three-month romance led to an engagement, marriage and the birth of Britney's sons Sean Preston Federline and Jayden James Federline. However, after two years of marriage, they were divorced with Federline suing Britney for custody during a particularly trying time for the singer.
Britney Records "Toxic" And The World Thanks Her
Also known as the best Britney Spears single of all time, and the only one of her efforts to ever win a Grammy ("Best Pop Song," 2004). While the $1,000,000 music video for the track featured Britney Spears as a sexy stewardess who manages to join the mile-high club and kill someone with poison, the track's electropop glee comes from a killer chorus and dazzling string arrangement.
Britney Gives Birth To Her Sons Jayden and Sean Preston
While Britney lost custody of her two sons Jayden and Sean to her ex-husband Kevin Federline in 2007, she fought hard to win back her children. She regained custody of her kids in 2011 after reaching a deal with Federline's lawyer. Today she is a proud mom and credits her two sons' influence on steering her career and sanity, telling MTV, "They just think of mommy as mommy."