Playboy founder and cultural icon Hugh Hefner died on Wednesday. He was 91. Hefner and his magazine became a symbol of the sexual revolution that took place in the mid-20th century. His work, which championed free speech and smut, changed publishing and pop culture, and left a lasting legacy that influenced celebrity culture and politics alike. “Hugh Hefner was a GIANT in publishing, journalism, free speech & civil rights,” Larry King wrote. “He was a true original, and he was my friend.” Following the news of his death, many friends, associates, and admirers remembered the legend.