Desperately Seeking Kelly Osbourne

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·Writer, Yahoo Entertainment & Lifestyle
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Kelly Osbourne (Getty Images)
Kelly Osbourne (Getty Images)

With few exceptions, celebrity interviews are a delicate balancing act on a multitude of levels.

If there's an event or brand involved, there's the trade-off of plugging the show or the product or the whatever in exchange for 15 minutes with said star, which almost always gets cut down — 10 minutes if you're lucky, five if you're not. There's negotiating with publicists and vetting of questions. There's the drive to honor your editor and publication's desire for news while not pissing off the people who gave you access to a celebrity in the first place. But when all the stars align — both literally and figuratively — sometimes magic can happen.

I'm hoping for magic when I arrive at Club Nokia in downtown L.A. one Saturday night, where Kelly Osbourne is hosting the 4th Annual NYX Cosmetics FACE Awards Show. The show has assembled a panel of celebrity beauty judges to help choose from six beauty vlogger finalists, each of whom have created a special video to the theme of "True Colors" — the concept, not the song — to showcase their makeup artistry in hopes of winning the title of Beauty Vlogger of the Year and the $25,000 purse that comes with it. This is my trade-off for getting to speak with Osbourne: Go to the show, speak with her afterwards. Considering her penchant for saying exactly what she thinks and damn the consequences, it's an opportunity I can't pass up. And hey, what girl doesn’t like to have a little fun with makeup?

But before we can get to the awards show, there's the pre-show VIP reception — a cocktail extravaganza filled with fashionable folk that clearly excel at being fabulous. I wouldn't say I feel out of place — I have my notable style moments, just like any other girl. But as someone who makes an effort yet frequently finds her eye makeup sliding down her face despite what's touted as the industry's best finishing spray, yeah. You could say I feel a little bit intimidated.

Kelly had fun hanging with the six finalists (Getty Images)
Kelly had fun hanging with the six finalists (Getty Images)

This is only exacerbated when, while waiting at the elevators to take my seat for the show, I’m approached by two men who I'm sure are twins. One has an insanely glorious mane of hair, and he's dressed in flowing black garb of some sort — I can't tell if it's an adult onesie or two pieces — accented with a belt featuring a giant gold lion's head.

"Excuse me," he says in a friendly but regal tone. "Do you have a sticker on the back of your pass?"

I flip over the VIP lanyard I’m wearing around my neck. "Nope."

“Oh,” he says, and seems disappointed. “Never mind. Thank you.”

And he glides away, twin in tow, leaving me to momentarily wonder what kind of glory that sticker brings to its wearer. But the elevator is here and we're 10 minutes to showtime, so it's time to get going.

With my ticket in hand and a VIP wristband acting as my accessory for the evening, I am finally ushered to my seat and find myself at the edge of a balcony, sitting in a row reserved for press. This is one of the good parts about getting to do things like this — usually, they make sure you get great seats for whatever you're covering. Now if the show is entertaining, that's a bonus.

"There'd better be gift bags," I hear someone gripe. Next thing you know, Karmin has taken the stage to sing some hits, including "Brokenhearted," and the show is off to a solid start. Osbourne comes out soon after to thank the nominated vloggers for "making the world a more beautiful place," and sharing themselves with the world.

"Vlogging," Osbourne muses aloud. "Doesn't vlogging make you sound like a pervert when you say it?"

Osbourne then introduces the judges: Ve Neill, who's an award-winning makeup artist that's worked on films such as Beetlejuice, Mrs. Doubtfire, and The Hunger Games. Grav3yardgirl, a vlogger with 5 million subscribers and a Teen Choice Award nomination. Vegas Nay, a 20-year makeup pro with couture fashion lineage and a massive social media following. And then there's Jade Taylor, a senior beauty editor with Nylon.

Kelly takes a seat on Ve Neill's lap (Getty Images)
Kelly takes a seat on Ve Neill's lap (Getty Images)

While Osbourne seems to be having a great time, not everyone finds her approach as charming. I overhear an audience member murmur, "Kelly is the worst host. She keeps mispronouncing names!" True, but Osbourne calls herself out on it later, and also makes fun of herself for it. Sometimes there are people who just can’t be pleased, no matter what you say or do.

Despite another audience member's assertion that "we're going to be here all night," the show wraps up reasonably fast — honoring Mykie of Glam&Gore as the Beauty Vlogger of the Year. We're soon jettisoned back to the club to wait for the opportunity to interview Osbourne. This is where the adage of "hurry up and wait" holds true, as a collection of media sit around and make small talk, waiting for the real reason they're all there — to get Osbourne to say something buzzworthy.

We figure out who's going first, who's going last, and where we all fit on the interviewing food chain. We sip water. We watch the vloggers come out — some looking stunned by the whole experience — and witness them documenting every moment of post-show bliss for their social media followers. Patrick Starrr, who is resplendent in a jumpsuit and turban ensemble, stands off to the side, texting in a quiet moment as the more boisterous girls squeal and giggle and worship at the feet of Ve Neill.

Kelly strikes a pose with vloggers Patrick Starrr (L) and Rosy McMichael (Getty Images)
Kelly strikes a pose with vloggers Patrick Starrr (L) and Rosy McMichael (Getty Images)

"Kelly's coming," they say. "She's on her way," they tell us. "She's almost here." And then she is, having traded out her heels for flats and taking a seat on a couch across the room, ready to receive the media. One by one we're shuttled over, each of us hoping for some kind of magic to transpire, in which you make enough of a connection with your subject in a small window of time to allow them to say something wonderful, insightful, and newsworthy — and hopefully not say the same exact thing to the person who comes after you.

Then it's my turn.

"I love your lipstick," she says.

"Thanks," I tell her. "It's MAC Dangerous."

"Oh, I was going to wear that tonight, because it matched the shoes I was going to wear!" she squeals. "But then I looked at the size of the heels, and thought about how long I'd be standing, and decided, 'Eh, better wear another pair of shoes.'"

We sit. We chat. I get seven minutes. It's enough. Perfect, even.

Related: Kelly Osbourne Isn't Gonna Stop Saying What She Thinks

At the end, Osbourne stands up and pulls me into a warm hug.

"Thank you so much," she says, and having dealt with my fair share of bulls--ters, I can tell she means it.

"And thank you – you're awesome," I tell her, and I mean it too.

And then we're done. The moment is over. She's on to the next one. And I'm off to the Target Terrace for the post-show reception, where I pass that stylish twin and his lion's head belt on my way to peer over the edge of the railing at the busy city street below.

Oh, and in case you were wondering? There was a gift bag, and it was spectacular.