From the day he left St. Louis for New York as a teenager to the day he died, Miles Dewey Davis III was the coolest motherfucker on the planet. I don't say "motherfucker" to be vulgar; it was Miles's favorite word. In his 400-page autobiography, it appears 312 times. Miles used "motherfucker" the same way people from Philly use "jawn." It had no inherent definition to Miles, and its meaning changed according to the context in which he used it. It's impossible to summarize Miles's eccentric life and unparalleled career as a musician, painter, and fashion icon with one word, phrase, or sentence, but this seems fitting: Miles Davis was a real motherfucker.

Often to the chagrin of fans and critics alike, Miles's music constantly evolved; he never made the same record twice. His long close friendship with composer Gil Evans lead to experiments in jazz orchestration that sound fresh and original even 60 years later. Some believe Miles abandoned jazz altogether with his push into fusion with albums like Bitches Brew (1970) and On the Corner (1972). After resurfacing from a five-year retirement, Miles continued to earn the scorn of jazz traditionalists by wholly embracing the modern synthesizer sounds of the 1980s, culminating in a testy public feud with a brash teenage trumpet prodigy not unlike Miles at that age, Wynton Marsalis.

In his own words, Miles changed music "five or six times." That might even be undercutting it. At just 18, he played an integral role in the bebop revolution in the late 1940s, becoming the regular sideman for the art's brightest star, Charlie Parker. He was the band leader for the nonet that produced the first cool jazz recordings in 1949, a series of 78s that were later compiled as Birth of the Cool (1957). His great quintets—which made stars of now-legendary musicians John Coltrane, Cannonball Adderley, Wayne Shorter, Herbie Hancock, Chick Corea, and Tony Williams just to name a few—recorded albums that are definitive for almost every major subgenre of jazz at the time, including hard bop, post-bop, modal jazz, and fusion.

Miles Davis's personal life was no less controversial than his music thanks to the boundless hubris that came with his relatively privileged upbringing. He earned the nickname "the Prince of Darkness" in the media with venomous critiques of white America and aloof and erratic stage behavior that sometimes bordered on hostility, particularly in front of white audiences. His showy fashion sense and taste for expensive cars made him a target of racial profiling from white police, leading to a number of high-profile run-ins with the NYPD. He was rarely faithful to the seemingly hundreds of women he saw, and he admitted to multiple instances of domestic abuse. There was hardly a person in his life whom Miles didn't berate at one time or another in his distinctive raspy voice.

But there was noise that came out of Miles Davis other than insults: the sound of his trumpet. His sandpaper voice and his brilliant trumpet sound perfectly symbolize Miles's duality. Like Kanye West, he was as hard a person to love as he was a genius, and that's saying something, because his genius was a motherfucker.

So you want to get into: Miles Davis the Bebopper?

Miles Davis moved to New York City in 1944 ostensibly to attend the prestigious music school Juilliard, but the 18-year-old prodigy had an ulterior motive: find Bird. Charlie "Bird" Parker was leading the bebop revolution in clubs along 52nd Street and in Harlem. Miles had been transfixed by the art since hearing Bird and Dizzy Gillespie play in St. Louis a few years prior, and like Bob Dylan moving to NYC to find Woodie Guthrie, Miles was dead set on joining them. Bird took an immediate shine to Miles, and soon the budding duo was playing together regularly. Miles's laid back solos were the perfect complement to Parker's furious fits of notes, but, more importantly, Miles organized and booked gigs and recording dates for their group. Bird was so hopelessly addicted to heroin that getting him to even show up was a challenge in itself, and Miles served as both sideman and caretaker to the troubled genius.