With her topiary quiff, snug tuxedo, gospel-diva pipes and slip-sliding snake-dance moves, Janelle Monáe is a genetic meld of early James Brown, Jackson 5–era MJ and Annie Lennox at her most glossily robo-androgynous, and her television debut, on Late Show with David Letterman on May 18, 2010, heralded the birth of a star. The song she performed that night was “Tightrope,” a jaunty ode to equanimity in the soul-funk spirit of the Dap-Kings, backers of Sharon Jones and the late Amy Winehouse — except that, unlike those retro-cool front women, Monáe seems derivative of everyone and no one at once. She’s an impish, impeccably tailored cyborg, an emissary from days of future past, yet an entirely new species. Even if her concept album The ArchAndroid didn’t catch the fire that its irresistible lead single set, the 26-year-old Monáe remains one of the most promising talents of a still-young century, and this song is the evidence. “We call that classy brass,” indeed.
(Browse the All-TIME 100 Songs and more than 100 other pop culture lists on TIME’s Populist iPad app)
Next ‘Wake Up’