55. Playboy V1 #1 (Marilyn Monroe) Impeccable Condition
Manufacturer: Playboy
Original price: $0,50*
Value today: Up to $635,000*
The first 50-cent copy of Playboy Magazine featured the iconic Marilyn Monroe. Original, mint-condition copies of this magazine (especially those signed by Hugh Hefner himself) are worth thousands of dollars. The 1953 edition, released in December of that year, became a precious piece of Playboy history.
Marilyn Monroe and Playboy had a complicated relationship. The beautiful star helped launch Hugh Hefner's career, and he fell in love with her. The two never met in person, but Hefner paid US$$60,000 to be buried in a crypt next to her. She never posed exclusively for Playboy, but Hefner refused to ever let her go, even in death.