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How Kacy Hill Signed With Kanye West and Became the Most Exciting Pop Singer of the Year

By Michael Hafford

It’s Monday night at West Hollywood’s Peppermint Club, and Kacy Hill is shrugging her way onstage in a sparkling Gucci pantsuit. The crowd, for a debut singer, is beyond starry. Calvin Harris stands next to me—all 6’6” of him; Miguel sits at a table in the back; legendary party photographer Cobrasnake flits around, taking pictures of the guests; Hill’s best friend and fellow former American Apparel model Megan Fay stands in the front row. We’re all there to hear Hill perform some songs off her debut LP, Like a Woman, out now after a grueling three-year recording process. Though Hill’s entrance is bashful and her stature diminutive, she commands the room with an easy grace. Maybe that’s due to some liquid courage; Hill tells the crowd that she’s just downed a shot-and-a-half of tequila backstage.

The room, packed from entrance to exit, gets incredibly hot almost immediately. Hill sheds her jacket before singing “Cruel,” the third song on her album, revealing a lace top. Like the DJ Mustard-produced title track and second single, “Hard to Love,” the production is on the sparse side. You won’t find any big Phil Spector horn sections; Hill’s delicate but powerful voice does most of the heavy lifting. In a summer that’s already seen Lorde release an album and Miley a single, Like a Woman may be the best pop release of the year. That’s partially down to a come-to-Yeezus moment last year, when Hill played her single, “Lion,” for album executive producer Kanye West. “Wow, I hate it,” was how Hill described West’s reaction from stage. So back to the drawing board and, now, back with a spectacular debut.

Hill’s road to the Peppermint Club was windier than the western contortions of Sunset Boulevard. Born in Arizona, her early family life was marked by divorce, remarriage and re-divorce. Multiple times, Hill grew close with step-families, only to never speak to them again. As a result, she’s developed a fierce independent streak and, she tells me, has never been in a serious relationship herself. Hill moved to Los Angeles at 18, wanting to make some money before heading off to college. She told herself and her family it was a gap year, partially to give herself a backstop should things not work out.

Just two weeks after moving, her first friend in the city sexually assaulted her. Hill almost immediately began modelling for American Apparel, partially as a means of recovering control over her body and her sexuality. She tumbled into Kanye’s orbit and performed as a backup dancer on his Yeezus tour, spending hours “on stage in a mesh suit that flattered the female body like a sausage casing.” Hill left the tour before its completion to focus more fully on her music, which eventually landed her on Kanye’s G.O.O.D. label and, now, at the cusp of a serious moment as a pop singer.

Hill is personable and quick to laugh. She’s a self-described “lift bro” who can barely stay awake through the first 10 minutes of a movie. The day after her Peppermint Club show she came to Playboy HQ, where she discussed Kanye, how she grew stronger after her sexual assault, why she wants to collaborate with Harry Styles and much more.

Photography by Alexandra Gavillet
Styling by Lauren Matos
Hair and Makeup by Mishelle Parry


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