Stop The Presses! (NEW)

Britney Spears’s 30 Most Memorable Moments

Lyndsey Parker
Stop The Presses!

December 2 is a big day in the life of Britney Spears. It's her 30th birthday. She's not a girl and she IS a woman, y'all.  In her twenties, Britney experienced some big highs--and even bigger lows--but now her career and personal life seem to be back on track.  So to celebrate both her 30th birthday and her career rebirth, we're reviewing, in chronological order, the 30 biggest moments in her circus-like life.

Britney Wins, Then Loses, On 'Star Search'
Yes, people: Long ago, Britney Spears really was that innocent. In 1992, as an 11-year-old spitfire, Britney competed on the American Idol-prototype talent show Star Search, and man, was she ever adorable! She won the first round of competition, but was ultimately voted off...but regardless, a star was born. And oddly, she seemed to sing better when she was still a girl, not yet a woman. Just look at how she belts it out here:

Britney Rocks That Schoolgirl Skirt
One of the most iconic videos in MTV history, 1998's "Baby One More Time" instantly catapulted Britney, who was only 16 at the time, to pop-superstar status--and perhaps somewhat troublingly, it turned her into an underage sex symbol as well. Just what is about a school uniform that turns men to mush, huh?:

Britney's On The Cover Of The Rolling Stone
The questionable marketing of teenage Britney as a modern-day Lolita continued with her cover shoot--lensed by controversial photographer David La Chapelle--for Rolling Stone in April 1999. The image of Britney in skimpy sleepwear raised eyebrows/temperatures/concerns throughout the music world. Did it do any damage to Britney's young, developing psyche to be so obviously objectified? We'll never know for sure. But we do know that this provocative photo sure did sell quite a few issues of the magazine.

Britney Rocks That Bodysuit
At the 2000 VMAs, Britney ripped off her tuxedo to reveal a flesh-colored bodystocking that clung to every inch of her perfectly personal-trainered physique. Did she sing well? Was she lip-synching? Did it matter? This was the performance of a star, Britney at her sexy best.

Britney Is A "Slave 4 U"
Britney's metamorphosis from virginal, pigtailed America's sweetheart to full-on bombshell reached completion with the release of her third, self-titled album in 2001, and its seriously sexy lead single, "I'm A Slave 4 U." The song's video--in which a bunch of sweaty, grunty backup dancers got all up in Britney's bizness, and Britney inexplicably wore underwear on the outside of her pants (ironic, considering her tendency to forget underwear altogether later in life)--had a lot to do with that image makeover. But it was more than that. "Slave," written and produced by the Neptunes and originally intended for OG pop bombshell Janet Jackson, evoked the old-school sexcapades of Prince and his protégés Vanity 6--and in many ways, it was a real artistic leap for bubblegum Britney. But most Brit-pop fans probably paid more attention to her sweat-slicked six-pack and underwear-as-outerwear fashion sense than to her sophisticated new sound:

Snakes On A Dame!
Is there anything more fascinating, more compulsively watchable, than a nubile blonde pop goddess performing seductively with a live albino snake? We say no! This iconic, snake-charming performance--of the aforementioned "I'm A Slave 4 U"--was definitely the golden girl's shining MTV Video Music Awards moment. The folks at PETA were less than thrilled, but we're pretty sure no reptiles were harmed in the making of this performance. If anything, that snake was probably pretty dang happy:

Justin Gets The Last Word
Britney Spears and fellow Mickey Mouse Club alum Justin Timberlake were THE It Couple of late-'90s/early-2000s teen pop. But eventually they split up--like almost all celebrity It Couples eventually do--with Justin insinuating that the supposedly chaste Britney had actually been unfaithful (reportedly with choreographer Wade Robson). Britney stayed mum on the subject, but when her former *NSYNC-star boyfriend went solo, he got the last word with his "Cry Me A River" breakup ballad and video (starring a newsboy-capped Britney lookalike). Pop-music revenge had never been so sweet:

The Kiss Heard Around The World
Does anyone actually remember who won anything at the 2003 MTV Video Music Awards? Of course not. All anyone remembers about that particular VMA ceremony is the opening number featuring Madonna and the two logical successors to her pop-starlet throne, Britney Spears and her rumored rival Christina Aguilera. And the fact that it's the infamous Britney/Madonna smooch that remains ingrained in every VMA viewer's brain--Xtina got some sloppy-seconds liplock too, but everyone seems to forget that--only proves just how big a star Britney is and was:

Britney + Madonna = Blonde Ambition X2
At the time, "Me Against The Music" seemed like a classic baton-passing maneuver: elder stateswoman Madonna, once the Biggest Pop Star On The Planet, starring in a video with the New Biggest Pop Star, the one-and-only Britney. Naturally, some people accused Madonna of desperately trying to stay relevant by riding Britney's skimpy coattails. But years later, when Madonna's career was ironically in much better shape than Britney's, Britney did some of her own coattail-riding, starring in a promo film for Madge's stadium tour and making a surprise appearance at a Madonna L.A. show. Below is their duet from back in the day, when Madonna needed Britney much more than Britney needed Madonna. We'll see if Madonna will recruit Britney again when her next album comes out:

What Happens In Vegas, Gets Annulled In Vegas
2004 was the year everything started to go downhill for the once-untouchable, once-invincible Britney. It all started in January, when news broke that she'd impulsively married Jason Alexander in a quickie Vegas ceremony. Even worse, her new groom wasn't the Seinfeld funnyman, but some unknown childhood buddy who was now entitled to half of her fortune, since there was no prenup in place. Unsurprisingly, Britney's mama Lynne swooped in and made sure the marriage, which lasted only 57 hours, was swiftly annulled. At the time this seemed like just the crazy lost-weekend antics typical of any Vegas reveler...but it soon became clear that this was the beginning of troubled times for Britney. Jason was probably lucky to get out while he could, relatively unscathed, and he landed a book deal out of the whole experience.

Britney Commits "Suicide" In Music Video
In her disturbing video for "Everytime," Britney drowned in a bathtub after sustaining a bloody headwound. Originally the video was supposed to depict the pop star dying from a drug overdose, but the plotline was changed to avoid seeming like she was trying to glamorize suicide. But the impact was still intense. Looking back, the video now seems like a cry for help.

The Agony Of The Feet
Another sign that Britney was not that innocent--not to mention not that hygenic--was that infamous paparazzi photo of her exiting a gas station bathroom WITH NO SHOES ON. That's right--bare feet in a public restroom. Ewwww! This was one of the first pap shots of Britney looking unkempt and unclassy, and after this, the snappers hounded her everywhere she went, hoping to get a pic of her stuffing her face with Cheetos, picking her zits, looking bloated, etc. This became a cottage industry in the tabloid world, as Britney sadly gave the snappers plenty of opprtunities to capture her at her worst.

K-Fed Makes An Honest Woman Out Of Britney
No one quite understood what the Queen Of Pop saw in a pauper like wannabe rapper/backup dancer Kevin Federline. He had an eight-months-pregnant girlfriend, mic skills that would make Vanilla Ice balk, and an apparent allergy to soap. And yet, she claimed he was her "soulmate." And so, only six months after her ill-fated Vegas marriage, and only three months after she started dating K-Fed, she legitimately married Kevin in a private surprise ceremony in the San Fernando Valley. She seemed happy at the time, but we all know how this fairytale romance worked out.

Can We Handle Their Truth? Um, No.
As if she were determined to ruin her career--or at least determined to confirm the public's suspicions that her new husband was indeed a bottom-feeding slimeball--in 2005 Britters convinced the UPN network to air five episodes of her reality show, Britney & Kevin: Chaotic. Basically cobbled-together amateur nightvision footage of the couple talking monosyllabic nonsense about, er, the meaning of life 'n' stuff, this show was bad even by reality-TV standards:

Britney's Babymama Drama
Just four days short of their one-year wedding anniversary, on September 14, 2005, the Spederlines sired their first heir, Sean Preston. This seemed like a reason to rejoice, until...

Baby, One More Time
...Britney got pregnant again, mere months after Sean's birth. Second son Jayden James was born just two days shy of Sean's first birthday. Concerned citizens who'd watched the Spederlines' airhead antics on Chaotic secretly hoped and prayed that this couple would stop procreating, pronto.

Unsafe At Any Speed
Meanwhile, while Britney was incubating the unborn Jayden, her mothering skills were already the subject of much media scrutiny. Paparazzi shots of her almost accidentally dropping Sean on his soft little head, or gossip reports that she let her baby drink Coca-Cola, didn't help--but it was the photograph of her driving with an unseatbelted Sean on her lap that caused the real tizzy. Britney claimed she was trying to escape from the photographers and was trying to PROTECT Sean by driving away with him quickly, but no one bought that story. Later she wrote off the incident in her now-infamous Matt Lauer interview (see below), shrugging and saying, "We're country!"

Her Date With 'Dateline'
In an attempt to polish up her increasingly tarnished image after the seatbelt scandal and rumors of her marriage's impending demise, a pregnant Britney agree to sit down with Dateline's Matt Lauer for a candid, one-on-one interview. It was a bad idea. With no handlers, advisors, makeup artists, stylists, or other entourage members hovering around to make sure their star client didn't humiliate herself, Britney was left her own devices. The result was an absolute disaster that even the most skilled spin-controlling publicist couldn't salvage. She wore a third-trimester-inappropriate sheer belly-shirt and micro-mini; she snapped her gum like a cud-chewing cow throughout the interview; and she blubbered until her self-applied false eyelashes came unglued and snot ran from her nose. But hey, at least she spoke the truth...she did tell Matt, "I don't care what people think." Well, obviously:

Bazaar Baby On Board
Shortly before giving birth to her second son, a very pregnant Britney attempted to gain some post-Dateline-fallout cred by dyeing her bubblehead-blonde hair a more respectable shade of brunette, then she pulled a Demi Moore and posed unclothed for Harper's Bazaar. The artfully rendered Harper's pics of Brit in all her (meticulously airbrushed) glory were intended to obliterate all those Dateline images of the sheer-maternity-shirt-wearing, non-Kleenex-using, Bazooka-chomping "country" Britney from the public's minds forever. It didn't quite work.

Britney Texts Her Soon-To-Be-Ex
In November 2006, Britney proved there is such a thing as better living through technology by allegedly dumping Kevin Federline via text message while he was visiting Canadian channel MuchMusic to promote his "rap" album. K-Fed was soon not-so-affectionately nicknamed "Fed-Ex" in the blogosphere. Now, Fed-Ex was no prize catch, but this still seemed like a nasty way to dump the father of one's own children. Was what happened to Britney in the year following her divorce some sort of karmic payback? Who knows:

Britney's Panty(less) Raid
When Britney announced that she was divorcing Kevin Federline, the world rejoiced. She showed up on Letterman, looking radiant and blondely bobbed, and announced plans for a new album. And everyone thought, "Britney is BACK!" But it turned out reports of her cleaned-up comeback were greatly exaggerated. Soon she seemed set on derailing her trainwreck of a career once again, by hanging out with new bad-influence friends like Paris Hilton and Brandon Davis, sporting some seriously ratty hair extensions that even Ken Paves wouldn't peddle on QVC, and, most worryingly, developing what appeared to be an acute allergy to underwear. How else to explain Brit's most notorious online photo, er, spread, in which she seemingly forgot to wear not only panties but any sort of clothing from the waist down? Anyway, we know most guys would leap at the chance to see half-naked pics of Brit's bits, but trust us: These un-airbrushed JPEGs were not something anyone would want to see. They were positively toxic.

Hair Today, Gone Tomorrow
While Britney certainly provided the press with plenty of comedic fodder over the years, by the time she picked up those clippers in that tiny hair salon in Tarzana, her life just wasn't funny anymore. After skipping out of rehab in Antigua and hopping a plane back to the States, the seemingly unstoppable downward spiral of the fallen former teen star's life hit bottom with an all-night bender that included a bizarre public head-shaving and an impulse tattoo-parlor visit. Day later she was seen in public wearing a bad Halloween wig and a glazed-over expression. Clearly she needed serious, immediate help. And if she ever managed to stage a comeback, it'd be such an odds-defying feat, it'd make Mariah Carey's post-Glitter revival look like nuthin':

You Can Stand Under Her Umbrella, Ella, Ella...
Not long after that head-shaving incident, a bald-headed Britney was back at it, attacking a paparazzo's car with an umbrella and looking positively deranged. She later used some sort of vaguely Freaky Friday-ish excuse for this bizarre parasol-wielding behavior, claiming in a handwritten note that she was "preparing a character for a possible movie role where the husband doesn't play his part so they swap places." Wow, who knew Britney was such a devoted student of the Robert DeNiro school of method acting? Brit then added, "Unfortunately I didn't get the part; I'm sorry I got all carried away with my role!" Oh well. Maybe this could explain the head-shaving, too: Perhaps Britney was just getting into character for a V For Vendetta audition. And maybe her pantyless crotch-flashing was all part of some plan to star in Basic Instinct 3. Yeah, it all makes sense now:

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"Leave Britney alone!"

Chris Crocker Stands Up For Britney

This kid became an overnight viral video sensation when he demanded that the world "LEAVE BRITNEY ALONE!" The paparazzi and tabloid ignored this request, of course, and kept right on hounding her. But for about 15 minutes, Crocker's pro-Britney tirade made him just as big a star.

Britney At 2007 VMAs: Gimme Less, Please
Don't call it a comeback. Because it wasn't. Yes, the big hype surrounding the 2007 Video Music Awards was the fact that Britney Spears--a woman who'd made VMA history multiple times in the past by performing with an albino snake, tongue-wrestling onstage with Madonna, and somehow inadvertently giving Michael Jackson an "Artist Of The Millennium" award--would be kicking off that year's Vegas ceremony with a performance of her new single, "Gimme More." More like gimme less, thank you very much. With worse lip-synching than SNL-era Ashlee Simpson, clodfooted choreography that in no way reflected the hours of rehearsal time she'd reportedly logged at the Millennium Dance Studio, and utterly confused/disappointed expressions on the famous faces of spectators like 50 Cent and Chris Brown (too bad the cameras didn't cut to Justin Timberlake's surely priceless reaction)...honestly, Kevin Federline could have done a better job opening the VMAs. That performance was trainwrecky enough to make fans shave their own heads in protest, and it seemed once and for all that Britney's career was pretty much officially kaput. It was a very sad day for Britney fans:

Britney Gets Psyched
It didn't seem things could get any worse for poor Britney. But they did. Less than a year after the head-shaving incident, on the evening of January 3, 2008, Britney got involved in a standoff with authorities when she refused to relinquish custody of her children when reps for K-Fed came to pick them up on their visitation day. Men in white coats were called to the scene, and they carted her away to the Cedars-Sinai Medical Center for two days of psychiatric evaluation. The footage of her deer-in-lights expression as she was carried out of her home on a gurney--with her presumably frightened children still locked inside--is something that was truly to hard to watch. It made it clear just how much life in a fishbowl had taken its toll on the pop princess. Of course, that still didn't stop an opportunistic Dr. Phil from bumrushing Britney at her bedside.

Britney Gets Rid Of Zeroes, Gets With The Heroes
There was a time when the public blamed Kevin Federline for Britney's downfall: "Oh, if only she could get out from under Kevin's dead weight, all her troubles would be gone and her career would be back on track!" However, her downward slide into mental illness after their divorce--and Kevin's surprisingly decent parenting skills, which for a while earned him sole custody of Sean and Jayden--proved that K-Fed was not to blame. Britney was possibly her own worst enemy, but she also surrounded herself with agenda-wielding users who were no good for her, like married paparazzo boyfriend Adnan Ghalib and meddling Svengali manager Sam Lutfi. But after her hospitalization, the people who cared about her most--her family--stepped in to take back control of their daughter's empire. Britney's dad, Jamie Spears, secured conservatorship of her estate; a restraining order was issued against Lutfi; her old manager from her golden era, Larry Rudolph, stepped back into the picture; and Adnan, who'd started dating Britney a month before her big breakdown, was forbidden to contact Britney. Probably uncoincidentally, guest spots on How I Met Your Mother, three VMA moonmen, and a #1 single soon followed:

MTV Means Having To Say You're Sorry
A year after Britney's horrific, nearly career-killing "Gimme More" performance on the 2007 VMAs, the execs over at MTV were probably feeling a little guilty. Let's face it, they'd sort of sold her out, allowing her to perform when she was clearly in NO shape to do so, then reaping all the subsequent PR benefits. So for the 2008 VMAs, the network enlisted Brit to star in VMA promos with host Russell Brand, had her open the show in a skit alongside Jonah Hill, and gave her three token VMA trophies. Incredibly, Britney had never won a moonman before, not even for an awesome video like "Toxic"--and now she was sweeping the VMAs with "Piece Of Me," a video hardly anyone even saw. This was clearly a make-good attempt on MTV's part, sort of the equivalent giving Whoopi Goldberg the Best Supporting Actress Oscar for Ghost to compensate for not giving her a deserved Oscar for The Color Purple. But whether or not "Piece Of Me" was THE best video of 2008 (um, it wasn't), it was still heartening to see Britney, sequined and smiling, back on top:

DO Call It A Comeback!
In October 2008, Britney's single "Womanizer" zoomed from #96 to #1 on the Hot 100 chart, amazingly becoming her first #1 single since "Baby One More Time" in 1999. This leap set a record, at the time, for the biggest move to #1 on the Hot 100, and "Womanizer"'s debut at #1 on Hot Digital Songs chart, with 286,000 paid downloads, set a new record for the biggest first-week sales by a female artist. Wow...was Britney FINALLY launching the full-scale comeback we'd been hearing about for so long? Indeed she was. And she's been on top ever since.

Britney Wins The Michael Jackson Video Vanguard Award
Back at the 2002 VMAs, Britney introduced Michael Jackson as someone she considered to be "the artist of the millennium"--which somehow led a confused Jackson to believe he was receiving a special Artist Of The Millennium award, with him even mistaking a cheap styrofoam decoration on his onstage birthday cake for a VMA trophy. Awkward! Britney, as mentioned easlier, suffered her own awkward VMA moment five years later. But all was forgiven when Britney received a lifetime achievement award, named in honored of the late Michael, at the 2011 VMAs. It wasn't quite the tribute she deserved--much her speech time was taken up by a scripted introduction of VMA performer Beyonce, she didn't perform, and Lady Gaga's male-drag alter ego Jo Calderone tried very hard to upstage her. Not cool, MTV! But it was still nice to see Britney honored as an iconic, after her many, many high and lows.

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