The actress, who died aged 36 in 1962 in a suspected suicide, was the publication's first ever cover star in 1952 and she makes a return to the front page from beyond the grave in the December (12) edition.
Playboy staff spent six months trawling through an archive of more than 10 million photos to select the images of Monroe which feature in the tribute gallery, according to the New York Daily News.
The pictures chart the actress' career and include one of her most famous photos, when she posed naked on a red velvet cloth for snapper Tom Kelly.
Playboy founder Hugh Hefner says, "She was most in control when she was in the nude. What would be a position of vulnerability for others was a position of power for her."
The silent movie icon's trademarks went under the hammer at a Bonhams sale on Sunday (18Nov12).
The lot was expected to fetch no more than $60,000 (£37,500).
The ongoing auction also features a handwritten letter from John Lennon in which the Beatle sketched himself and wife Yoko Ono nude and an archive of Marilyn Monroe photographs.
The silent film icon's accessories will go under the hammer at the Bonhams pop culture sale in Los Angeles on Sunday (18Nov12).
The Chaplin lot is tipped as the highlight of the auction, but other items up for grabs include jazz pioneer Charlie Parker's saxophone, thought to be worth at least $22,000 (£13,750); a series of Marilyn Monroe photographs, priced at up to $20,000 (£12,500); and a handwritten letter from late Beatle John Lennon, which features a nude sketch of himself with his wife Yoko Ono. That is expected to draw bids of up to $22,000 (£13,750).
The white, puff-ball blouse and blue gingham pinafore, which the star wore to play Dorothy in the 1939 film, sold for $480,000 (£300,000) when it went under the hammer this week (ends11Nov12).
Garland's outfit is one of the most famous costumes in cinema history and although several identical ensembles were made for the movie, it was the only one to have been seen on film and the only complete version to have survived intact.
Other items which went under the hammer at the Julien’s Auctions sale in Beverly Hills, California included a pair of sunglasses famously worn by John Belushi in 1980 movie The Blues Brothers, which sold for $16,640 (£10,400).
A dress seen on Julie Andrews in The Sound of Music made $38,400 (£24,000) and a purple skirt worn by Marilyn Monroe in River of No Return sold for $50,000 (£31,250). A racing jacket owned by Steve McQueen also went for $50,000 (£31,250).
The Twilight star admits his decision to take the dog home was so impulsive he had to feed him prosciutto in his hotel room after agreeing to give the pooch a home.
He tells U.S. chat show host Ellen DeGeneres, "He was, like, five weeks old and he was in a five-day kill shelter... on his fourth day.
"A couple of days a later, just by coincidence, I had to go back to L.A... and we had like a private plane. So I took him from the worst pound in Monroe, Louisiana and he was sitting on a little private jet the next day.
"We were staying at the Four Seasons after (that) and I didn't have any dog food, so I got him a plate of prosciutto."
"One day we were walking along Broadway and nobody noticed. I couldn't believe it and I said, 'This is unbelievable! We're walking along, it's Marilyn Monroe, nobody's going crazy.' And she said, 'Oh, you want to see her?' And I said, 'Sure!' and all she did was change her body posture and all of a sudden within 10 feet we couldn't move. We were surrounded by people. It took five policemen (to escort us). She became Marilyn. That's a great movie star." Actor Burt Reynolds was mesmerised by the Some Like It Hot bombshell.
The 90-year-old piece of Tinseltown history depicts the Gentlemen Prefer Blondes stars, as drawn by artist Bill Mack, who bought the original Hollywood sign in 2007.
The piece will go under the hammer at a Profiles in History sale in Los Angeles in mid-December (12). It is estimated to fetch between $150,000 (£93,750) and $250,000 (£156,000).
The Hobbit star plays neurosurgeon Gabriel Monroe in the British show and in a bid to make his portrayal as realistic as possible, he attended up to five skull operations at a hospital in Leeds, England.
The actor admits he was apprehensive about watching the gory procedure, but once he had overcome his nerves he found the whole process fascinating.
Nesbitt tells U.K. TV show This Morning, "We were very fortunate in that I got to spend a lot of time with surgeons. I sat in on four or five brain operations. The first was extremely difficult. For the first one I was just stood at the back. I didn't know what was going on.
"To get into the brain is very agricultural and industrial - they're kind of drilling and sawing. Then the surgeon called me over. Once the brain is revealed it's a rather beautiful and stunning kind of organ... And he said to me, 'See that bit there? That's thought'."
"I saw The Seven Year Itch at about seven years old. That Halloween I was Marilyn Monroe in the white dress, with the mole. I went to the vintage Levi's store in London yesterday, and the lady said that the '50s jeans were the ones Marilyn Monroe used to wear - the same style. I'm still thinking about them. Maybe I'll get them for Christmas. Then I can look like Marilyn Monroe." Elle Fanning cites Marilyn Monroe as her Hollywood icon.
The mother of Grey's Anatomy actress Brooke Smith passed away on Sunday (07Oct12) after suffering a brain haemorrhage due to an accidental fall.
According to movie website Deadline.com, she tripped down a set of stairs on Saturday (06Oct12) at a bed-and-breakfast in Maine, where she was staying with her husband Eugene.
Her client list also included Robert Redford, director Martin Scorsese, Susan Sarandon, Whitney Houston and Marlee Matlin, who has taken to Twitter.com to pay tribute to her former mentor.
Matlin writes, "So sad to read about passing of publicist & friend Lois Smith. She helped guide me when I did (1986 movie) Children Of A Lesser God. I will miss her... RIP... She really set me on the right track when I was so new... She was a great lady."