Billboard Cover: Ariana Grande on Fame, Freddy Krueger and Her Freaky Past

The “micromanaging workhorse” finally achieved her dream of becoming an R&B diva. Now, at 21, comes the hard part: conquering her fear of futuristic pop.

Ariana Grande is easily mistaken for an old-school good girl. The singer wears Audrey Hepburn-style strapless gowns, travels everywhere with her mother and trades lovey-dovey messages with on-again, off-again boyfriend Jai Brooks (of Internet comedy boy-troupe The Janoskians) over Instagram. Last year, she implored fans to boycott SeaWorld after the damning documentary Blackfish came out.

"I think people see me as a little cutesy thing," she says, looking, in fact, demure and adorable, seated with her feet tucked underneath her on a giant leather couch. "But I’m literally the most sardonic person you’ve ever met."

Proud oddball Iggy Azalea -- Grande’s collaborator on "Problem," the song-of-the-summer contender that has elevated Grande to superstar status -- allows that Grande, while "very sweet," is definitely "quirky." Last year, bloggers simply had her pegged as a "mini-Mariah" for the lush, unabashedly ’90s R&B sound of her debut Yours Truly, which went to No. 1.

On Aug. 25, Grande presents her follow-up, My Everything, and three huge singles released in the run-up to the album have already redefined her as a state-of-the-art pop diva: Besides "Problem," a super-catchy, not-at-all-smooth, kiss-off track, there’s the Ibiza-ready "Break Free" and the woman-power anthem, "Bang Bang," with Nicki Minaj and Jessie J.

Grande, who now lives in Los Angeles, says she was "a very weird little girl" growing up in Boca Raton, Fla.: "Dark and deranged. I always wanted to have skeleton face paint on or be wearing a Freddy Krueger mask, and I would carry a hockey stick around. I was like a mini-Helena Bonham Carter."

Sitting in the cavelike lounge we’ve retreated to in downtown L.A., she looses a throaty, almost maniacal laugh. "For my fifth birthday party we had a Jaws theme and all my friends left crying. I mean, I still am that way. But when I was little it was more concerning. There was a stage, when I was 3 or 4, where my mom thought I might grow up to be a serial killer."

Instead, Grande embarked on a show-tunes-inspired career. She started acting in community theater a few years after the creepy birthday party, and by freshman year in high school, she auditioned and scored her first casting in a Broadway show, 13. That led to a supporting role on Nickelodeon’s teen musical sitcom Victorious and a starring part in the Victorious spinoff, Sam & Cat.

Republic Records chairman/CEO Monte Lipman signed Grande when she was 17 and little-known beyond Nickelodeon, after a friend excitedly sent him YouTube videos of her covering Whitney Houston and Mariah Carey. Sam & Cat only lasted one season; the final episode aired in July, amid much drama. But two weeks later, "Break Free" placed No. 1 on iTunes.

Making a hit record was always the goal. "I remember when I first came to L.A. to meet with my managers, I was like, 'I want to make an R&B album,' " recalls Grande. "They were like" -- she drops her voice a few registers --" 'Um, that’s a helluva goal! Who is going to buy a 14-year-old’s R&B album?!'"

Grande’s restless ambition is accompanied by a twitchy energy: She’s hummingbird-tiny at just five feet tall, often walking with a stutter step thanks to her giant high heels.

She makes dramatic arm gestures as she talks, with the words tumbling out of her mouth. "I am hypoglycemic so sometimes I’ll get anxious if I forget to eat," says Grande. "When I was a little girl, I would turn into the Tasmanian devil."

"Because she is a perfectionist, the one thing I’ll say to her every now and again is, ‘Ari, perfect is not always about being perfect -- it’s those flaws that people can relate to,'"says Lipman. "I don’t want you to get to the point where you’re gritting your teeth and your fists are all balled up."

Grande agrees. "I’m a micromanaging workhorse," she says, nodding vigorously. "Absolutely an obsessive-compulsive workaholic."

Even as an 8-year-old kid playing Annie, she didn’t want to stop working. "I just wanted to do every single show," she remembers. "However many there were in a year, I was in every one, whether I was a chorus girl or the lead or doing the lighting."

At that time, Grande’s older half brother Frankie claimed star status in the family. "My brother was always the one in the spotlight and I liked that," she explains. (Frankie’s a performer and producer currently working his outsized personality and dyed Mohawk on the deathless CBS reality show Big Brother.) "It was like he was the entertainment for me."

Grande’s mother is Joan Grande, who runs a telephone and alarm system company and moved with Ariana’s father from New York to Florida when she was pregnant with their daughter.

Grande’s father, Edward Butera, owns a successful graphic design firm in Boca Raton. "My brother and my mom and my grandparents were always there," she recalls. "And my dad, until my parents split up when I was 8 or 9."

The week I spoke with Grande was a rough one. Her beloved grandfather had just passed away at the age of 90, and she was posting photos of him -- as a dashing young man in a fedora; on his deathbed, Grande smiling by his side -- in online tributes. Like everything else, Grande shares her grief with her fans. In person, though, she struggles to articulate it.

"It’s just so fresh and I’m still mourning," she says in a whisper. "I don’t even know what I would say to be able to encompass what an amazing man he was." She wipes her forefinger delicately under each eye and smiles. "I mean, how much time do you have?"

While in Florida caring for her grand­father, Grande met up with her dad, whom she hadn’t seen in a while. "It was good," she says. "I love my dad." But she’s made no secret of the fact that her parents’ divorce and relationship with her father have been tricky. "Everybody with divorced parents knows what it’s like to be in the middle. Even years later I’m still in the middle."

Grande responded, in part, by cultivating interests from her grandparents.

"I have an obsession with all things vintage and classic and old-school, everything from Marlene Dietrich to Frankie Valli and The Four Seasons to Connie Francis," she says. "My grandpa was always telling me I should sing songs from the Great American Songbook."

But her most towering influence may be Madonna. After hearing Grande easily harmonize to Madonna albums all afternoon, I half joke that the two should do a song together.

"Oh my God, my heart would stop," she gushes. "She is strength, she is freedom, she is wisdom beyond anybody’s comprehension." Grande was raised Catholic but "departed from that and started practicing my own things when I was around 12 years old," she says. Now, like Madonna, Grande practices Kabbalah.

"As a fellow Kabbalist, I know how hard it is to exercise those tools in your everyday life," says Grande. "Especially in a world where everything is so egocentric and all you do is talk about yourself and promote yourself."

Of course, Grande has had to be a tireless self-promoter -- even after making it onto TV, she was posting homemade videos online. Her pleasures now are simple, even sparse: "The most relaxing thing to me is going to the beach at night," she says. "I mostly do it in Boca." She’ll rehearse with her dancers, even when there’s no event coming up, for the company.

And sometimes she’ll fly out her best friend Alexa Paige, a pal from Florida now in college, for fun. But she’s closest with her mother, who she calls "fierce," and her brother. They’ll play Heads Up! when a few free minutes open up. Frankie being away on Big Brother "is excruciating, because I have no communication with him, and he’s missed so many things."

The afternoon we spend together, Grande is surrounded by functionaries, but instead of a combination assistant-slash-best friend, it’s Joan who makes sure to bring her two bottles of water -- one cold, one at room temperature.

Grande’s also remarkably good at keeping her own counsel. "When she sent me 'The Way' featuring Mac Miller," Lipman recalls, referring to Grande’s first big single, "she goes, 'I just made a record that is a smash.'" When Lipman asked to start planning the video, she said it was already done. (It’s a sweet, simple clip in which a radiant Grande chastely flirts with Miller.) "

That video, which cost virtually nothing, is the only video we ever made for that song," says Lipman. "It’s got 100 million views, and at the end of the day, that was her."

In scaling up her sound for My Everything, Grande needed to sacrifice control. "Everything that I was terrified to try and was absolutely positive I would hate, I tried," she says, explaining that at first she was "intimidated" by "Problem" and wary of recording straight-up dance tracks.

"It’s not like, because Ariana has a huge range, she can only do that kind of music,” says her "Break Free" co-writer Anton Zaslavski, aka Zedd.

Grande wasn’t so sure. "I hated it at first," she says, describing her vocals on "Break Free," which she sings ahead of the beat. Co-producer Max Martin convinced her to sing in what she calls a "more forward placement."

"I was like no, no, no! Please just let me sing it how I would sing it," she mock-whines. "But he was like, 'Just try it. Trust me.'" She loved the results. "I was so pleased when I tried something that I thought -- no, that I knew I would hate."

"Problem" was also a difficult sell. "I loved the idea of it, but the chorus, the whisper was so shocking to me," says Grande, referring to the unexpected, intimate refrain sung by Big Sean -- "I got one less problem without you" -- which co-writer Savan Kotecha first dreamed up in an airplane bathroom, and completed for Grande after he was brought in to work on My Everything.

("I sang it into my phone," he remembers. "I had that voice in my head for a year.")

In the main part, she wanted to show off more of her range -- her "normal, I’m-not-screaming voice." But "what makes an Ariana song an Ariana song is that it’s a song no one else can sing," says Kotecha. "She’s probably one of, if not the best, technical singers of her generation."

"When I was 14, I wanted to make a straight-up, like, India Arie record," remembers Grande, laughing. "Something really soulful." Is it her inner Bonham Carter that pulls Grande toward what she calls "the bittersweetness" of soul music?

"Maybe," she says, sighing. "I honestly think it could be a past-life thing. You know those things where you love something but you don’t know why, or you’re scared of something but you don’t know why? I feel like all of those things are from another life."

Obviously there’s more to Grande than a shrill, tightly wound diva in training -- Election’s Tracy Flick with a four-octave range. She displays a thoughtfulness and a weirdly sane-seeming mysticism that suggest true depth.

Balancing real life as a person and unreal life as a famous person is a big part of what Grande works on these days.

"I never thought it would be a thing for me to go out in my pajamas," she says.

Does she feel pressure to hide aspects of her private life? "I do and sometimes I don’t. I vacillate between saying, 'I need to keep some things private' and 'I should be able to be myself, and I need to share what I love and everything with the world!'"

Grande’s also hard at work planning live shows to support the new album. "I did a tiny tour, but it was very small and intimate and on not much of a stage,” says Grande of the shows she played last year, opening up for Justin Bieber.

"It’s new, very new. It’s going to be a big shock for me. Here’s the thing," she says, leaning forward and speaking in a conspiratorial whisper.

"I have to launch this album, and I get to do a tour, which all sounds fine and dandy...but I just love being in the studio. I could start a new album right now, tonight. That sounds the most enticing to me. I love it."