When asked by Dick Clark on American Bandstand in 1983 what her dreams were, a young Madonna replied, "To rule the world." She proceeded to do just that, releasing eleven blockbuster studio albums to date and becoming the world's top-selling female recording artist ever. The mother of reinvention, she has endlessly reworked her image and style, affecting our culture in myriad, rippling ways. Though she's sometimes criticized for following fads in her personal life, when it comes to her music the culture usually mirrors her. -Rebecca Haithcoat
14. Caetano Veloso
Branded the Bob Dylan of Brazil, Caetano Veloso co-founded Tropicalia, the progressive poetry, theater and music movement that helped define Latin America's psychedelic '60s. Alongside his fellow conspirator, Gilberto Gil, Veloso fused Bossa Nova, African rhythms, and acid-drenched acoustic guitar with a political consciousness that found him censored, banned, incarcerated and eventually exiled by the country's military dictatorship. The recipe was complex but simple: melodies as gorgeous as a Copacabana beach layered atop of a philosophical wit exposing his homeland's most gross imbalances. -Jeff Weiss
13. Fela Kuti
Raised in Lagos, schooled in London, and radicalized in L.A. at the height of the Black Panther movement, Fela Kuti pioneered Afro-Beat — a blend of James Brown, Nigerian highlife, and pan-African ideals. A decade and a half after his death, he's the subject of a Tony-nominated Broadway musical, two sons are gifted heirs to his sound, and he's a sub-Saharan icon almost on par with Mandela. Yet beyond the myth are the songs: jazzy 12-minute sagas with a timeless sense of rebellion, fearlessness, and funk. -Jeff Weiss
12. Miles Davis
Somehow in his more than forty years of recording, Miles Davis never drifted into irrelevancy. He was an intense and spiritual figure who refused to be pigeon-holed by any single style of expression. Through his trumpet playing and band leadership, he constantly sought new ways to manifest improvised performance. This rejection of the status quo put him at the forefront of major developments in jazz and rock last century - including bebop, cool jazz, fusion, and even jazz hip-hop. No one else in music can claim such a long reign as the King of Cool. -Chris Walker
11. Billie Holiday
Billie Holiday didn't write that many of her songs, but her gift, like that of an inspired classical musician, was in the interpretation. Her voice summoned that which was dramatic, urgent and necessary as if from the center of the earth. Today's politically-minded performers could take inspiration from her protest music; she knew that imagery and real soul impact listeners more strongly than corny, overly-dogmatic messages. -Ben Westhoff
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