In the late 2000s, social media gave misfits and outsiders the means to carve out their own personal space online, and attract legions of followers by presenting the most raw and unfiltered version of themselves. And no artist personified that moment quite like Kesha Rose Sebert (born 1987), the brash, potty-mouthed, nose-ringed anti-diva who crashed the Top 40 through her wailing cameo on Flo Rida’s 2009 synth-rap chart-topper, “Right Round,” and then stuck around like she owned the place. At a time when EDM-infused maximalism was reshaping the sound of pop music, Kesha united club kids, hip-hop heads, and indie hipsters under one festival tent through bratty bops like “TiK ToK” and “We R Who We R.” And she was also the rare omnivorous pop star who was just as eager to record Stooges tributes with psych-pop kings The Flaming Lips (“2012 [You Must Be Upgraded]”) as hook up with dance-rap pooh-bah Pitbull for his 2013 strobe-lit smash “Timber.” Behind the scenes, however, Kesha’s life was no party—a struggle with eating disorders and a nasty legal battle with her former producer, Dr. Luke, brought her career to a halt. By the time Kesha resurfaced with 2017’s Rainbow, she was being celebrated as an icon of the burgeoning #MeToo movement, and the album’s spirit of empowerment and emancipation filtered down to its non-conformist sound, which foregrounded the country, soul, and classic-rock influences she inherited from her musician mother, Pebe (who also guested on the record). And 2020’s High Road found her reclaiming the more sexualized persona of her earlier work, while doubling down on her reputation as pop’s most unpredictable polymath—who else could trade verses with NOLA bounce deity Big Freedia, collaborate with Grimes, and harmonize with Brian Wilson and Sturgill Simpson on the same record? “I’m not going to let something that happened to me in my past define who I’m going to be the rest of my life,” “This record is me being like, ‘No—you’re not going to stick me in some box.’”