Hugh Hefner, the founder and avatar of Playboy, died of natural causes on Sept. 27 at age 91. With his characteristic smoking jacket, pipe, and bevy of Playboy Bunnies at his side, Hefner became a controversial pop culture icon who built a publishing and entertainment empire which put conservative views of sex and sexuality that defined America in the 1950’s squarely in its crosshairs.

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Photo by Larry Hulst/Michael Ochs Archives/Getty Images

Before Jimi Hendrix was a living icon, knocking out psychedelic guitar riffs and counterculture ballads that remained relevant after his untimely death on Sept. 18, 1970 — 47 years ago — he was a soldier in the U.S. Army. The man who once set his left-handed Stratocaster ablaze after playing it with his teeth wore olive-drab fatigues and a military cover before swapping them in for tie-dye shirts and headbands. But the way he left the service was as epic as any of his guitar licks.

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