The incredible life and times of Hugh Hefner, in pictures

Travelling in style! Hef and his girlfriend at the time, Barbi Benton, on board his his luxury DC-9 aircraft “The Big Bunny” at Heathrow in 1970.

Flanked by two iconic bunnies, including former girlfriend Holly Madison, the trio film a scene at the Playboy mansion for a video game commercial in 2003. “I have about 100 pairs of pyjamas. I like to see people dressed comfortably,” he’s said of his quirky get up.

A young Hugh jokes about with Joan Bradshaw at one of his famous Playboy parties in 1957.

He was never without his beloved smoking pipe!

Hef wed Playmate of the Year Kimberley Conrad in 1989. They share two sons, Marston, 27, and Cooper, 26.

The family man: The doting dad spends time with his then-wife Kimberly Conrad and their son Marston at the Playboy Playmate Of The Year Celebration in 1991.

This is one of the last photos of Hef and his grown-up sons, taken back in June this year. “Backgammon with the family #FathersDay,” Cooper captioned it.

The dapper entrepreneur enjoys a stiff drink in the company of a very pretty woman at a Playboy shindig in LA in 1957.

The editor and his cover girl! Hef cuddles up to Cynthia Maddox on a super-jet in Chicago in 1962. She’s also gracing the mag’s February edition in his hands.

The mogul was never without a bevy of blondes by his side…

We’re not joking!

A polygamist at heart, the star was very much from the school of thinking the more girlfriends, the merrier!

“There were chunks of my life when I was married, and when I was married I never cheated. But I made up for it when I wasn’t married. You have to keep your hand in,” Hugh’s said.

The 91-year-old has estimated to have slept with over a thousand women in his time.

“How could I possibly know? Over a thousand, I’m sure,” he told Esquire in 2013.

It doesn’t get more ’90s than this! The Playboy founder made loads of TV and film cameos – who could forget his starring role in an episode of The Fresh Prince of Bel Air.

One of his last public outings was for his birthday in April. Here, Hef and third wife Crystal Hefner pose with his cake. “Thank you for all the birthday wishes,” he said at the time.

“In my wildest dreams, I could not have imagined a sweeter life.”

Hef always dreamed big, cutting his teeth as a copywriter for Esquire in 1952 he left the company to launch his own publication – Playboy. It would go on to become one of the most revolutionary, controversial and iconic magazines of all time.

To this day, the Playboy empire is still worth millions.

One of the great loves of his life, Holly Madison. They were together from 2001 until 2008.

Pamela Anderson plants a wet one on the man who helped launch her career.

Proof he’s not just into blondes! In the ’60s and ’70s, Hugh fell madly in love with his Playboy After Dark co-host and singer Barbi Benton.

Before his disgraceful downfall, Bill Cosby was a welcome guest at the mansion.

Hef and his girlfriends Holly and Bridget cut some mad shapes on the dance floor during his 81st birthday bash in Las Vegas.

Hugh found a whole new generation of fans thanks to his insanely successful show The Girls of The Playboy Mansion, which chronicled his life with live-in girlfriends Holly Madison, Bridget Marquardt and Kendra Wilkinson.

The women went on to become stars in their own right.

“He was a #Legend, innovator & one of a kind. We had so many fun & incredible memories together. I will miss him dearly. Rest In Peace my friend,” Paris Hilton has said in a heartfelt tribute.

You can tell it’s the ’90s thanks to those over-sized specs! The father-of-four puckers up to kiss a pretty blonde at yet another party at the mansion in 1998.

“Life is too short to be living somebody else’s dream,” he once said.

“For me, the magazine was always the heart of what my life was all about, and the other half was living the life.”

“My best pick-up line is ‘My name is Hugh Hefner!”

RIP, Hugh Hefner.