Playboy founder Hugh Hefner died at his Playboy Mansion home on Wednesday due to natural causes. He was 91.

An iconic name behind an even more iconic brand, Hefner was one of America’s best-known businessmen, a media magnate conquering more than five decades in the publishing industry.

Hefner was working as copywriter at Esquire in the 1952 when he left after being denied a $5 raise. The first issue of Playboy was released just a year later with just $8,000 in investments — $1,000 of which came from his mother. That issue sold more than 50,000 copies.

More than sixty years and even more Playboy Bunnies later, the magazine sells millions of copies each month and Hefner passed away with a net worth of $50 million.

Hefner was considered a leading charge in the sexual revolution of the 1960’s, despite some controversy over the magazine’s emphasis on nude women and sexually-charged content. But although the magazine is known for its adult material, it also quickly became a coveted and highly competitive byline for journalists.

Outside of the business, Hefner found love — repeatedly. He wed three times: First, to Mildred Williams, before he became “the” Hugh Hefner; second, to Kimberley Conrad; and third to Crystal Harris, whom he married in 2012. Although he was legally married to each woman, he famously maintained sexual and romantic relationships with other women in the Playboy Mansion.