Is Britney Spears the Oldest 33-Year-Old in Show Business?

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A veteran entertainment journalist looks back at the long, hard road the young star has taken—and whether her most recent comeback will stick.

One of the perks of being a veteran entertainment editor at fashion magazines has been the opportunity to watch the likes of Beyoncé, Miley Cyrus and Rihanna literally grow up before my eyes—and evolve from awkward albeit preternaturally driven teenagers into the global superstars of today. I have also relished the opportunity to peer behind the curtain of Photoshop and see these young women as they really are, warts and all. Or, more accurately, pimples and all, regardless of whether or not they happen to have an endorsement deal with Proactiv.

Back in 2002, I flew a writer from New York to interview Britney Spears at the four-bedroom, Tudor-style home she had built on a 7.5-acre estate in Kentwood, La. I was a senior editor for InStyle magazine, and at the time, Spears was the only 20-year-old on the Forbes list of the world’s most powerful celebrities—she ranked fourth, in fact, while Oprah came in at number 9. From all outward appearances, Britney had a firm grip on fame, fortune and reality.

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Of course, the best part of editing a celebrity cover story is hearing the story behind it. After reading the bubbly transcript, I asked the writer how she managed to get Britney to open up. "I got her drunk," the writer joked. At least, I thought she was joking. But the cover girl herself admitted to underage imbibing, revealing a fondness for the occasional cosmo or Midori sour. "I don't know what’s in them, but they sure taste good," Britney said. "I think if you do everything in moderation, it's OK. The only thing I’m addicted to is taking baths at night."

That was then. Flash forward to 2006: After two failed marriages, a custody battle and a few new possible addictions, Britney outed herself as an "emotional wreck" during an interview with Matt Lauer. She proved her point the following year by pathologically flashing the entire world via the paparazzi and shaving her head for the cameras to boot. Additionally, she made a few visits to rehab and attempted to joust a photographer’s car with a green umbrella. Her first comeback album attempt, Blackout, was released in 2007 with almost no promotion, and a listless VMAs performance of "Gimme More" didn't do anything to stop the skid.

The downward spiral continued as Spears was charged with a misdemeanor hit-and-run and lost custody of her kids (to Kevin Federline, of all people). Then, on Jan. 3, 2008, the pop princess was carried out of her LA home on a gurney and rushed to Cedars-Sinai Medical Center. "Britney had postpartum depression, which [in addition to]…the end of her marriage to Kevin and the enormous pressures of her career, brought her to the breaking point," reported Britney's mother, Lynne Spears, in her jaw-dropping tell-all book, Through the Storm. "Something inside of her had broken and needed to be healed."

That much seemed obvious. But after Britney was released on Jan. 5, she was hospitalized again within a few weeks. (That ambulance ride was memorably escorted by 12 motorcycle officers, a couple of police cruisers and two helicopters for good measure.) The next day, while Britney was locked in a psychiatric ward, her father, Jamie Spears, signed documents in court that stated his daughter was "in an immediate and substantial medical emergency."

With her dad's help—which was not optional (he became her court-appointed conservator A.K.A. the boss of her life)—Spears started her journey of recovery and soon regained visitation rights with her beloved boys. Similarly, in the following months, Britney began her carefully calculated career resurrection: Working out regularly, recording a new album and an opening skit at the MTV VMAs in September of 2008 while rocking a sexy silver dress courtesy of Donatella Versace. She took home three trophies that night, including a Video of the Year award for her single "Piece of Me."

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Once her CD-in-progress, Circus, secured a release date of Dec. 2—Britney's twenty-seventh birthday—I managed to secure a global exclusive for Glamour’s January 2009 issue, which meant that my Q&A would simultaneously appear in foreign editions all around the world.

There was just one catch, according to the publicist at Britney's record label. I had to promise not to ask about the one subject everybody wanted to read about: the breakdown. Her A&R rep, Teresa LaBarbera Whites, had acknowledged that "Britney went through a dark time" while previewing a few tracks for me in the studio. Reluctantly, though, I was forced to comply—but my journalistic integrity got the best of me in the end.

I was hoping to get the scoop at the cover shoot while Britney was in hair and makeup. But since she had arrived late—with bits of weave from VMA night still glued to her head—hairstylist Chris McMillan had his hands full and needed his space. So I decided to wait until Britney was in between wardrobe changes and asked her point blank about her well-chronicled battle with mental illness, which I wasn't sure was over yet. During that afternoon, she alternated between shaky, spacey and sleepy (much to my horror, at one point she even left Patrick Demarchelier’s set to take a nap). When I eventually brought up the subject of depression, Larry Rudolph—who has micro-managed Spears’ career since age 15—cut me off and answered for her: "That's beyond what we want to talk about," he snapped.

That said, Britney at least alluded to the insanity: "This whole year has been a hell of a year for me…this has been a crazy year," she understated. Of her comeback, she said: "I have 'come back' so many times, people are just like, Is this another one? It's kind of like a joke to me now." At least she was in on the joke, I thought. Britney added that she hated going out to clubs and instead preferred to watch Dancing with the Stars in bed or read a Danielle Steel novel.

The conversation turned to her likely New Year's resolutions ("to stop worrying so much because I worry all the time. And to learn how to be happier, just in general"). I also asked about Britney's plans for the future. "I would love to have a lot of albums under my belt. And a couple of movies," she said. "In five years, I would like to be married and have a father figure for my kids, someone who is a provider and can be really stable. It's hard doing it on your own," Spears added with a sigh.

It is now precisely five years later and after 15 years in the spotlight, Britney seems like the oldest 33-year-old in show business. She recently suffered another breakup (with ex-boyfriend David Lucado) but only a few months later, Spears is on the rebound: She was spotted frolicking on the beach with a new beau, Charlie Ebersol, and her kids Sean Preston, 9, and Jayden James, 8, over the Thanksgiving holiday weekend. "So grateful for family time this weekend. My boys!" Britney tweeted to her 39.7 million followers. (She also has 42.5 million fans on Facebook and 3.7 million followers on  Instagram.)

Her eighth album, Britney Jean, released in December of 2013, turned out to be the worst selling studio album of her career. But let's put it in perspective: Britney has already sold more than 70 million albums worldwide, which perhaps explains why she still took home the trophy for Favorite Pop Artist at the 40th People's Choice Awards last January.

These days, album sales are not where the money is at, anyway—it's all about branding. And so in July, Britney launched her newest perfume, Stage Fantasy. She has pocketed over a billion dollars since launching her fragrance line with Elizabeth Arden in 2004. (Granted, Spears is still under conservatorship hence not in control of all that bank she’s managed to keep making.) She's breaking into the fashion industry, too: Britney officially launched her Intimate line of lingerie, which she also allegedly designed, in September and proceeded to promote the collection all over Europe.

While hawking her overpriced undergarments in London, Britney spilled some details about new album in progress. "I'm gonna have a lot of 'I hate men' songs and then a lot of 'I love men' songs [on it]," the singer told On Demand Entertainment! To ensure that her ninth CD sells better than Britney Jean, she's reportedly hoping to attract A-List collaborators like Gwen Stefani, Katy Perry and Iggy Azalea.

"What's indisputable is that Spears is one of the leading heritage artists of her generation," noted And so there will inevitably be legions of nostalgic fans willing to pay for the privilege of a Britney-guided tour down memory lane to the soundtrack of their youth. The pop icon is currently performing her "Britney: Piece Of Me" residency show at Planet Hollywood in Las Vegas, which was scheduled to wrap in February but has reportedly been extended until 2017 due to popular demand. (It has already earned her upwards of $20 million.)

So what if she got to Sin City 20 or 30 years ahead of schedule? She's more than keeping up with Celine and Elton. Maybe she even inspired J.Lo, who's rumored to be joining that pack at the not so advanced age of 45. Despite having weathered as much drama as divas twice her age, this year Britney landed ahead of both Nicki Minaj and Madonna to secure the number 10 spot on the Forbes list of Highest Paid Women in Music.

Which proves that after 15 years of ups and downs, hit songs and dirty dancing, nobody puts Britney in a corner.