Drake Co-Signed Singer Alessia Cara on Her Rising Fame: 'It's the Coolest Fluke Ever'

Meredith Jenks
Alessia Cara photographed by Meredith Jenks on July 31, 2015 in New York. 

For her first-ever TV performance in July, on The Tonight Show no less, Alessia Cara opted not to wear a designer -- or even slightly showy -- look. The stage lights rose to reveal the singer, 19, in the casual, woke-up-like-this uniform favored by teens everywhere: ripped jeans, Chuck Taylors and an ironic T-shirt (it read "Life of the Party"). The only semblance of flare was winged eyeliner, done up a la her idol Amy Winehouse. But when she sang, she became as transfixing as a mirrored ball, swaggering into The Roots' pocket like a pro. "I was overwhelmed with joy," she says. "I was so flustered, I didn't know what to do with my body." Until Jimmy Fallon put his arm around Cara and walked her to the edge of the stage to face her new fans. "You belong here," he said.

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It was a moment -- not just because the teen born Alessia Caracciolo shot to No. 1 on Billboard's Twitter Emerging Artists chart the day after, but because of the song she performed: "Here," a sultry soul hit explicitly about not belonging. While her peers on the Hot R&B Songs list (where "Here" is No. 7 in its 12th week) make like modern Caligulas, Cara lyrically paints herself as an "antisocial pessimist" who'd prefer to be wherever the red Solo cups aren't. "She speaks for a new set of kids that grew up on the Internet and don't care about what everybody else wants them to be," says Dion "No I.D." Wilson, ­legendary producer (Common, Big Sean) and ­executive vp A&R at Def Jam, which will release Cara's Four Pink Walls EP on Aug. 28 in partnership with EP Entertainment.

The irony of her success isn't lost on Cara. "It's the coolest fluke ever," she says over the phone from a mini-tour in Australia, her first trip there. "Now I get to do all these crazy things. It's like jumping off a cliff."

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Her Instagram feed is full of tourist faves from recent tour stops around the world: the Eiffel Tower, the Golden Gate Bridge, a crimson British telephone box. She's equally geeked over Twitter love from Lorde and Taylor Swift and social media follows from Drake that turned into a real-life ­introduction. "I'm going to take that as him wanting to do an album together." She jokes, but it was YouTube covers of those three stars, among many others, that led to Cara's discovery.

Cara grew up on the outskirts of Toronto in an Italian home, her mom a hairdresser from Italy who initially spoke little English, her dad a first-generation welder. "My house was very strange," she remembers. "I didn't do things other kids did because my parents were very strict -- I stayed at home, quiet in my room."

The singer entertained herself with poetry, and she and her younger brother had a highly creative lying phase where they would make up stories about being ­kidnapped by bus drivers or becoming doulas to pregnant earthworms. "I liked the idea of people being fascinated by my tales," says Cara. "I was a troublemaking kid. But now, it's like the heavens punished me, and I tell too much truth."

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She also sang a lot, in the closet, when no one was home. When Cara finally sang for her mother -- "I made her close her eyes because I was so shy" -- the woman cried and told Cara what she says she already knew: "I was meant for this."

Around age 13, Cara posted her first YouTube cover (Jessie J's "Price Tag") at her mom's urging. Dad was skeptical, but when EP Entertainment reached out, he was the one who took her to New York to talk shop. She signed a management deal at 16, and her dad has been by her side since -- literally. "He's with me right now," Cara says with a laugh. "There was no way he was going to let me do this by myself. And life can get lonely -- it's good to have someone you can trust."

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She has found a co-writer who fits that criteria too: EP's Sebastian Kole (Jennifer Lopez), who helped Cara find her voice by having her email him daily diary entries. Producers Pop & Oak (Rihanna, Nicki Minaj) came later, sampling the Isaac Hayes song ("Ike's Rap II") famously looped on Portishead's "Glory Box" and further ­shaping her sound: confessional alterna-pop that spans deep soul, folk balladry and trip-hop. Cara managed to keep her musical journey under wraps from ­classmates, who found out she had signed to Def Jam only after she walked at graduation. "I wanted to get through high school anonymously," she says. "I didn't want to be that girl in the hallways."

Now, she has a full-length album slated for the fall. It'll be called Know It All, and though she claims the title is sarcastic (naturally), the tattoo on her wrist suggests more wisdom, and self-confidence, than she lets on. "It's a paper sailboat," says Cara. "They seem so frail, but when you put them on water they float. It's a reminder that even though I'm small and seem weak, I'm not."

Additional reporting by Kathy Iandoli.

Listen to music from Alessia Cara, and more artists from this issue, in the Spotify playlist below:

This story originally appeared in the Sept. 5 issue of Billboard.