Mandy Moore: Adult Entertainment

Mandy Moore is standing in the middle of an art gallery in Chelsea, New York, gazing perplexedly at an enormous canvas. Understandably: It depicts nude people strung with IVs, monkeys in cages and a dying shark on the floor. It’s a gorgeous Saturday, and the place is packed with art–fiend hipsters and bespectacled aficionados, and nobody — literally nobody, not even a Japanese camera crew — is paying Moore the slightest mind. It’s not like she didn’t make an entrance, with her surprising height, her aura of celebrity perfection, her cascade of auburn hair and the whopping knee–high black cast she’s wearing on her right leg (the result of a fractured ankle), which hitches her walk with a dramatic limp. But the pop singer turned actress seems to have plunked down exactly in the center of her least–likely demographic.

Moore hunches her shoulders, uncomfortable–teenager style, and gimps into the second room of the gallery. Another crowd of serious people; again, no flicker of recognition. She seems to relax. And then she gets to the final room. There are four skinny African–American kids — boys, 13 or 14 years old, tops — clustered around an oil painting of a man’s naked torso and hairy groin. Moore stares at its companion piece, a portrait of a nude woman, and sighs, mystified, “I just don’t know the rules of art.” The kids start murmuring, conferring among themselves. As Moore turns and walks out, one of the kids trots out behind her, then yells, “Hey! You Mandy Moore?”

Everyone is weirdly still. Moore tucks her chin into her shoulder, half come–hither, half dying of embarrassment, and says, “Mm–hmm.” She hobbles out to the sidewalk, the kid in hot pursuit. He thrusts a piece of paper her way and asks for an autograph. With an enormous smile, she chirps, “Of course!” and signs it To Malcolm, Love Mandy, flourished with a big, script–y heart.

And here is the strange state of Mandy Moore, the most lovable of all the teen chicklets hatched in the late–’90s Orlando–based pop–music boom. Ask a grown–up, and they might have some inkling of who she is — didn’t I see that Diane Keaton bomb Because I Said So on an airplane? — but she’s not exactly in their mainstream. Ask anyone who was stuck in high school at the turn of the millennium and they can rattle off Moore’s most famous accomplishments: her MTV staples — the teensploitation breakthrough “Candy” and the treacly “I Wanna Be With You” — and her starring role as a tragic leukemia girl in the pubescent love story A Walk to Remember. But it’s the grown–ups whom Moore, 23, is setting her sights on now. It’s the grown–ups for whom she’s writing music. And it’s the grown–ups who will determine whether Mandy Moore is going to be a musical somebody — or just another pretty actress with a hobby.

Her new CD, the aptly titled Wild Hope, is a determinedly adult singer–songwriter record that evokes Lilith Fair more than TRL: strummy guitars, melancholic keyboards, gently rocking Americana drums, intense lyrics about breaking up and standing on your own two solid, womanly feet. It’s well–played, well–meaning, fair–trade–only–coffeehouse music, performed with a shy charm, and just about as far away as Moore can get from the bubblegum that made her famous.

The middle child of an airline–pilot dad and a former–journalist mom, Moore got her first recording deal at age 14, when a local FedEx employee heard her at an Orlando studio and sent her demo to his friend, an A&R rep for Epic. Her first album, So Real, was released in 1999, and she promptly began touring with fellow Floridian juggernauts ’N Sync and the Backstreet Boys. “I went straight from watching them on TRL to opening for them in front of 20,000 people,” she says with amazement. “I don’t know where that confidence came from — and I don’t know where it went.”

Moore was always the awkward–little–sister figure in the oversexed–teen–star pantheon. She didn’t have the breathy bustiness of a Jessica Simpson, the taut abs of a Britney Spears or the tiny, porny proportions of a Christina Aguilera. And yet in her first video, for “Candy,” she works the camera in a way that’s almost upsettingly suggestive, with heavy–lidded upward glances and a pout. She says, “It’s funny: I think that was my sexiest time, at 15 — my gawky body, swaying like a little stick figure. My most overtly sexy thing was the first one, right off the bat.” She makes a fake–sad face, pulling the sides of her mouth down. “And from there it was aaallll covered up.”

Over the past few years, Moore has made a habit of ostentatiously ragging on her teen output. “How accountable can you really be when you’re a kid in an adult world?” she asks. “There was no way they were going to give me any say over my music or my image at that point. But even at the time, I was like, ‘Oh, gosh, I really don’t like this song … ’”