A career-long chronicler of New York streets, Lou Reed (born Lewis Allan Reed in Brooklyn in 1942) fleshed out the city’s fringes with serpentine tales of blurred genders and late-night misadventure. Musically, Reed maintained a chameleonic presence from album to album, dramatically changing his sound while staying continually ahead of the times. A young student of doo-wop and free jazz alike, he became an in-house songwriter (and occasional session player) for New York’s Pickwick Records in his early 20s, toying with unconventional guitar tunings and other avant-garde touches lifted from his cross-genre spectrum of influences. There he met Welshman John Cale, with whom he cofounded The Velvet Underground before entering the orbit of cutting-edge pop artist Andy Warhol. The band’s first four albums before frontman Reed departed in 1970 have provided an undiminished north star for underground rock ever since. Even after scoring a crossover hit with 1972’s hummable urban postcard “Walk on the Wild Side”—produced by David Bowie and Bowie’s guitarist Mick Ronson—Reed didn’t stick to pop-friendly glam but followed it with the throwback orchestral flair of Berlin. Further experiments included the industrial noise and drone of 1975’s Metal Machine Music as well as other ambitious concept albums and winding, suite-like structures, all guided by a grainy drawl that often swerves into streetwise talk-singing. Reed’s soaring piano ballad “Perfect Day” was repurposed to heartbreaking effect in 1996’s Trainspotting, and Reed remained relevant right up until his death in 2013, collaborating with Metallica, Gorillaz, and his wife Laurie Anderson. He remains an eternally cool spirit guide for new generations of misfits and outsiders.