Hugh Hefner pulled back and forth on his decision to axe nudes from Playboy more times than… no, we’re not going to make that joke.

However, one constant the magazine achieved under his 63-year stewardship is featuring the world’s most beautiful and high-profile women (in one NSFW way or another).

To honour the silk pyjama-clad mogul, who this week made his way to the big mansion in the sky at the age of 91, we’ve picked 25 of the publication’s best covers, from the fifties right through until now, from the funny to the downright filthy. Thanks, Hef.

Who: Kelly Brook

What: Actress
When: September 2010
Why: Kelly Brook was promoting an iconic piece of cinematic history, Piranha 3D. To be fair, Kelly in 3D does sound like a great idea.

Kelly Brook Playboy

Who: Carmen Electra

What: Actress
When: April 2003
Why: Building hype for another iconic piece of cinematic history, Baywatch: Hawaiian Wedding.

Carmen Electra Playboy

Who: Jaime Pressly

What: Actress
When: February 2004
Why: Jaime Pressly was promoting Fast & Furious rip-off, Torque – and clearly that wasn’t the only thing getting ripped off.

Jaime Pressly

Who: Vida Guerra

What: Glamour model
When: July 2006
Why: Men’s mag regular Vida Guerra wanted “to show the world what she really looked like naked” following a phone-hacking incident. Message received.

Vida Guerra

Who: Marilyn Monroe

What: Actress
When: December 1953
Why: The first ever cover of Playboy required a serious icon – so who better than the most iconic woman of her era?

Marilyn Monroe

Who: Donna Michelle

What: Glamour model
When: May 1964
Why: Hefner was looking for a model who could contort her body into the infamous bunny logo. Amateur gymnast turned model and actress Donna Michelle was the obvious choice.

 Donna Michelle

Who: Janet Pilgrim

What: Playboy office worker
When: July 1955
Why: Janet Pilgrim was working for Hefner in the subscriptions department when he whisked her away to become Playmate of the Month. Talk about a promotion.

Janet Pilgrim

Who: Darine Stern

What: Model
When: October 1971
Why: Model and all-round seventies babe Darine Stern was the first African-American model to be featured on the cover by herself.

Darine Stern

Who: Pamela Anderson

What: Actress
When: October 1989
Why: Vogue has Kate Moss, Playboy has Pammy. The current Ms Assange has a whopping 15 covers under her belt – and this was the first.

Pamela Anderson

Who: Anna Nicole Smith

What: Model
When: June 1993
Why: Anna Nicole Smith was Playmate of the Year in 1993, just a year before she married 89-year old billionaire James Howard Marshall II. Why not?

Anna Nicole Smith

Who: Jenny McCarthy

What: Comedian
When: January 2005
Why: Jenny McCarthy was generating buzz for her film Dirty Love, for which she won the Razzie for Worst Actress, Worst Screenplay and Worst Picture. Still, the cover’s not half bad.

Jenny McCarthy

Who: Kate Moss

What: Supermodel
When: January 2014
Why: Kate Moss was celebrating the iconic magazine’s 60th-anniversary edition, photographed by legendary fashion photography duo Mert & Marcus.

Kate Moss

Who: Alina Puscau

What: Model
When: November 2009
Why: Poor Alina Puscau. Despite being one of the hottest cover stars ever, the Romanian model, actress and singer had to share the cover with Springfield’s hottest mama.

Alina Puscau

Who: Marge Simpson

What: Housewife
When: November 2009
Why: Marking 20 years of her family being on screen, Marge Simpson stripped down in the style of Darine Stern to become the first animated character to grace the hallowed cover.

Marge Simpson

Who: Naomi Campbell

What: Supermodel
When: December 1999
Why: In 1999, Naomi Campbell entered rehab for cocaine addiction, so Playboy offered some good PR to the brands that stuck by her.

Naomi Campbell

Who: The Trio From Rio

What: Triplets
When: November 1993
Why: Marilise, Lilian and Renata Porto became the most famous triplets in the world following their record-breaking sister showing on the cover of Playboy.

The Trio From Rio

Who: Robin Givens

What: Actress
When: September 1994
Why: Mike Tyson’s first wife was once called ‘the most hated woman in America’, but this centrefold spread swiftly changed hearts and minds.

Robin Givens

Who: Sharon Stone

What: Actress
When: July 1990
Why: Two years before she wowed with a lot more in Basic Instinct, Shazza stripped bare for this cover to coincide with the release of Total Recall and promptly rocketed up the A-list.

Sharon Stone

Who: Kim Kardashian

What: Full-Time Kardashian
When: December 2007
Why: Following the leak of her sex tape, the future Mrs West took ownership of her own sexuality by releasing this smoking shoot which was also documented on Keeping Up With The Kardashians, naturally.

Kim Kardashian

Who: The Barbi Twins

What: Twin Models
When: September 1991
Why: The Barbi Twins’ issue sold out within two weeks, so it’s unsurprising the sisters landed both the Playboy billboard and another record-breaking cover a year later.

The Barbi Twins

Who: Cindy Crawford

What: Supermodel
When: October 1998
Why: Cindy Crawford had just launched her Sex With Cindy show, so it was only natural she’d eventually pose nude for the Bunny Press.

Cindy Crawford

Who: Jessica Alba

What: Actress
When: March 2006
Why: With the title of ‘Sexiest Woman In The World’ under her belt bikini bottoms, who else would nail the cover quite like Jessica Alba?

Jessica Alba

Who: Sally Field

What: Actress
When: March 1986
Why: The only multiple Oscar winner on the list, serious auteur Sally Field donned the bunny outfit and gave a deep insight into her mind with an in-depth interview.

Sally Field

Who: Lindsay Lohan

What: Actress
When: January 2012
Why: Lindsay Lohan may prefer her Burkini these days, but back in her hedonistic heyday she was much more at home in the buff.

Lindsay Lohan

Who: Tamara Ecclestone

What: Heiress
When: May 2013
Why: Her dad, ex-Formula One boss Bernie, may have said he’ll never look at the images, but Tamara Ecclestone’s rightfully proud of her nearly-nude cover, decked out in (what else?) diamonds.

Tamara Ecclestone