My Day With Britney Spears From Sketchers To Tears

The Day I Made Britney Spears Cry

My very first job out of college was as Associate Editor of a now defunct teen mag called SuperTeen. If you were a kid between 1996 and 1999, and loved Backstreet Boys or Hanson, there is a slight chance you may have read an article penned by me. That job was the coolest. Although it paid a measly $21,000 a year in 1997 (meaning it was bad even back then), it allowed me some pretty cool perks. 

In addition to lots of free beauty products, I had backstage access to countless concerts, Disney cruises, dinners at Hard Rock and Planet Hollywood sitting next to whoever was the hottest kid at the moment. I’ve interviewed everyone from Jonathan Taylor Thomas to Justin Timberlake. From Beyonce to BackStreet Boys, even Hanson—very not the nicest child stars by way, although Taylor wasn’t as obnoxious as Ike and Zac. 

Why am I telling you this? 

I got an email from Ian over at Daily Dose of Reality asking, “Who is the most famous person you’ve ever met?” I’m guessing that’d be Britney Spears.  My final big assignment prior to a layoff, (the magazine was acquired by competitors and some messy crap went down aka eventually everyone ended up getting canned) I was to spend the day with Britney in NYC. Our offices, of course were in NYC, so we were always busy with press events, etc.

It was a Spring day as I waited on the corner of 18th and Park Avenue South for her to pick me up. OK, so Brit wasn’t behind the wheel exactly, her chauffer was.  Her label, Jive, often taxied their stars around in shiny black Cadillac Escalades.

I hopped in and slid up alongside her in the backseat and asked how she was. I hadn’t seen her in a few months. She had just returned from Japan—I think it was her first visit, but I could be wrong.  Killing time in Manhattan traffic, Brit showed me some little trinkets she snagged in Japan. I believe we bonded on our love for Hello Kitty and Sanrio as she showed me a light-up animated character connected to her cell phone. Nosey and always looking for something to chat about, I asked to see what was in her purse. I believe she pulled a few items from her wallet. I recall a pressed four-leaf clover for luck (I forget the story behind it) and a prayer she said kept her grounded and in touch with her faith.

Around this time, she was preparing for a big solo tour sponsored by Tommy Hilfiger. Hilfiger asked her to load up on some clothes. Whatever she wanted. Racks and racks of expensive designer fashions, all for free. I bitched to Tommy's brother Andy Hilfiger about how I couldn’t believe they still didn’t make any cute stuff in plus sizes for us bigger chicks. He apologized. Yeah, I’m ballsy like that.

I remember one puffy white jacket Britney tried on, I busted out with the lamest comment ever, “Gee Brit, for some reason I feel like if you were to fall into a swimming pool wearing that, you just might float.” Nobody laughed. Eek. I have a knack for saying stupid things, but don’t worry, it gets worse.

After the free Hilfiger shopping trip ended, we headed out to a photo studio loft in Union Square.  Upon exiting the Cadillac, Brit noticed a Sketchers store below the photo studio and tore-ass in there. Her very large bodyguard Rob, chaperone/family friend Felicia and I all followed her in as fast as we could.

While quickly surveying the store, I grabbed a cute pair of Adidas wannabe white platform sneakers and called to her, “Brit, get these! Get these! How cute are these?!” I was floored when she replied, “Oh yeah girl, those are cute! I have to have ‘em!” For some odd reason, I expected her to say, “Grab a pair for yourself, ya know since you found ‘em first.” Um, she didn’t.

Instead Felicia grabbed the platform Sketchers in Brit’s size and whipped out a credit card from her wallet. She joked with me about Brit being a shopaholic as her bodyguard grabbed a pair of Timberland looking Sketchers. This broke-ass editor left empty-handed of course. It’s okay; I’ve never been a big Sketchers fan anyway. I’m more of a Vans or Etnies girl myself.

Once inside the photo studio, Brit had her hair and makeup done while we sat around and chatted. Another editor was there at that point and we admired Britney’s Tocca candle and asked her what beauty products she liked, etc. Around this time, Brit was dealing with a lot of bad press and negative attention because of her fake boobage.  We knew enough not to mention that, yet I still managed to somehow screw that up.

During a few photos, Brit decided to go bra-less and when she went in to change into something else, I quietly mentioned to the photographer that anything too sexy would not make it into our magazines. Somehow she figured me out and the vibe seriously shifted from there. It was so awful, I wanted to die. I couldn’t apologize because I was too ashamed and didn’t know exactly what to say.

The next thing I knew, she was sitting in her makeup chair, getting hair and makeup touch-ups and sniffling. I could tell she was trying not to cry, cry. How could she possibly have heard me? How did she know what I said? I was so slick, so I thought. Maybe she thought I was making fun of her? Maybe she thought I saw her boob job scars? I had to make it better and had no idea how. Suddenly, the other editor kicked the weirdness up a notch and brought awkward to a whole new level.

I wish I could remember if I had told the other editor what had happened and she attempted to save the day, or if she just got all emotional herself totally at random. The next thing I know, Brit’s still in her makeup chair and editor lady is removing a necklace along with a locket or pendant type charm. She’s handing it over to Britney. I lean in to see what the hell is going on. She holds Britney’s hand and tells her that the necklace brought her only good luck and she felt it was time to pass it on to someone else. Uh, hello? This is Britney Spears, she gets free diamonds! Save your gold locket for your first-born.

Britney was gracious and they sniffled together as I stood there feeling like a total jerk. I began counting the minutes until I could finally go back to the office and hide in my cubicle writing up the “Day with Britney” story leaving out all of the juiciest parts. Thanks to Ian, I’m able to tell the real story.

Be sure to check out the image of Britney in her Sketchers that I PICKED OUT along with scans of the 1999 caption story. If you’re bored, click on the images to enlarge and enjoy. The story appeared in a tabloid style mag the new publishing company test-marketed. It failed. Why? Because even though I wasn’t the smoothest operator, I was their best reporter and I was now no longer contributing to their publications.  Trust me, I was the one editor who sweet-talked a 17-year-old Backstreet Boy Nick Carter into say anything other than, "Yeah, well ya know" or "I guess."  More on that another day.