At the age of 91, surrounded by friends and family, Hugh Hefner passed away yesterday.

The entrepreneur, who became an American institution with the launch of Playboy in 1953, did a whole lot more than just print pictures of nude women.

He was also able to build a brand that defined the sexual culture of the second half of the 20th century and was known as an advocate for civil rights, gay rights, freedom of speech and sexual freedom.

Here are some photos from his seven decades in the spotlight.

Hefner views photographs in his Chicago office.

Hefner is pictured amid a group of Bunnies, at the flagship Playboy Club, in Chicago, in 1960.

Hefner and his girlfriend Barbara Benton, 19-year-old coed turned actress, are surrounded by Bunny Girls at the Playboy Club in London, on Sept. 5, 1969.

Hefner, second from left, poses in front of his five and a half million dollar black jet plane with unidentified Playboy Bunnies. Chicago, 1970

Hefner shown with a Playboy Magazine and Playboy video. Undated

Hefner pushes his wife, Kimberly, on Schwinn’s limited “Black Phantom” bicycle, Jan. 10, 1996, at their home in the Holmby Hills area of Los Angeles.

The Hef in 2002.

Kendra Wilkinson, Bridget Marquardt, Hefner and Holly Madison at Virgin Megastore in New York, October 2005.

Hefner poses for photos at the Playboy Mansion in Los Angeles.

What a babe.

To all you who had high hopes of being his next girlfriend, I am sorry for your loss.

[source:channel24&indiewire&stltoday]