Hugh Hefner, the publishing powerhouse who founded Playboy magazine in 1953 and challenged puritanical convention, died Wednesday at the Playboy Mansion, leaving behind a legacy that his son, Cooper Hefner, will carry on in his absence. In celebration of Hugh's numerous accomplishments, the magazine shared some of the editor's favorite covers with E! News and other outlets, featuring Pamela Anderson, Jenny McCarthy and Anna Nicole Smith.

"A lot of people would kill to have my life and I understand that," Hugh, 91, once told E! News. "I am a kid who dreamed impossible dreams. I am the luckiest guy on the planet and I know it."

Hugh Hefner

Courtesy of Playboy

Hugh's impact on the publishing industry won't soon be forgotten.

"From the very start, Playboy was about more than just the beautiful women featured in its pages. Mr. Hefner took a progressive approach not only to sexuality and humor, but also to literature, politics and culture," the magazine said in a press release. "Within its pages, Playboy published fiction by such writers as Ray Bradbury, Charles Beaumont, John Updike, Ian Fleming, Joseph Heller, Gabriel Garcia Marquez, Margaret Atwood, Jack Kerouac and Kurt Vonnegut." To this day, the magazine is published in more than 20 countries around the world.

Take a look at some of Playboy's most iconic covers:

1953 Playboy Cover

Playboy

1955 Playboy Cover

Playboy

1964 Playboy Cover

Playboy

1965 Playboy Cover

Playboy

1969 Playboy Cover

Playboy

1971 Playboy Cover

Playboy

1989 Playboy Cover

Playboy

1993 Playboy Cover, Anna Nicole Smith

Playboy

2005 Playboy Cover, Jenny McCarthy

Playboy

2009 Playboy Cover

Playboy

2013 Playboy Cover, Kate Moss

Playboy

2014 Playboy Cover, Kate Moss

Playboy

2016 Playboy Cover, Pamela Anderson

Playboy

Information regarding Hugh's memorial services is not available at this time.

For more on Hugh, watch Daily Pop today at noon at E! News tonight at 7 and 11, only on E!

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