0 Britney Spears' Most Outrageous Moments

Britney Spears is only 30 years old, but she's endured enough controversy to last several lifetimes. The pop princess has been generating headlines for all the wrong reasons since the start of her career, but her enduring success is a testament to the world's continued fascination with her every move.


Rare is the woman who can shave her head, pummel an SUV with an umbrella, get committed to a psych ward, and emerge relatively unscathed, ready to dominate the Billboard 200 once more.

Here's a quick look at some of Britney's most outrageous moments — including those that landed her in our list of the Most Shocking Moments in Music History (oh, there are several).

1. Her Raunchy First Rolling Stone Cover
Not yet 17 when her first single, “...Baby One More Time,” broke in a big way, Britney terrified conservative parents everywhere with her constant suggestion of teen sex. On her first Rolling Stone cover, an open-mouthed Spears clutched a pink phone in one hand and a purple Teletubby—the sexually ambiguous Tinky Winky—in the other, her toned and tanned midriff on display atop pink satin sheets.

2. Quickie Marriage
Within a year of breaking up with her boyfriend of three years, fellow pop superstar Justin Timberlake, Britney had tied the knot with her childhood friend Jason Alexander at The Little White Wedding Chapel in Las Vegas. Everyone who's anyone has had at least one quickie wedding! Though the marriage was annulled within 55 hours, the incident marked the dawn of Britney's new "bad girl" image.

3. Kiss, Kiss
Britney, Christina Aguilera and Madonna opened the 2003 VMAs with a shocker as they traded smooches during a squeaky rendition of "Like a Virgin." Despite being the only singer on-key, Aguilera found her contribution overlooked as Britney and Madonna's spit-swap stole headlines. To think this was once shocking behavior from Britney...

 
4. Baby Daddy Boyfriend
A few months after her annulment, Britney announced her engagement to Kevin Federline, a backup dancer with a taste for tattoos. There was, of course, a major hitch: Federline had been attached to actress Shar Jackson for years before Britney came along. Jackson, who was pregnant with Federline's second child when he and Spears began dating, wasn't above talking to the tabloids about the scandal either. Also scandalous: The fact that Britney frequently walked around without any shoes during this time. Ick.

5. Partying Without Underpants
In 2006, Britney Spears became part of an exclusive but, uh, overexposed crew when she partied with Paris Hilton and Lindsay Lohan without any underwear on. And then she repeated herself a few nights later, perhaps not realizing how not-cute the "Oops... I Did It Again" jokes would be when they involved flashing her nether regions.

 
Bald, bald Britney. (Bauer Griffin)
6. Sinead O'Rebellion
Britney Spears' weave situation appears to be under control these days, but it suffered for years in the wake of a Tarzana, California, head-shaving incident in 2007, just a day after leaving an Antigua rehab center. A little less than a year later, she was committed to the UCLA Medical Center psych ward, and has been under the conservatorship of her father ever since.


 
Music's Most Outrageous Moments
Fortunately for Britney, she isn't the first musician to generate more press for her personal life than her professional accomplishments. No: Rock stars have been keeping it fascinating for years. See what rock 'n' roll legends are made of in our juicy new feature about music's most outrageous moments!