Maker: Playboy 
Original Price: $0.50*
Worth Today: Up to $635,000*

The first fifty-cent copy of Playboy Magazine featured the iconic Marilyn Monroe. Mint-condition, original copies of this magazine (especially those signed by Hugh Hefner himself) are worth thousands of dollars. The 1953 issue, released in December of that year, has become a priceless piece of Playboy history.

Marilyn Monroe and Playboy had a complicated relationship. The beautiful starlet helped launch Hugh Hefner’s career, and he became obsessed with her. The two never actually met in person, but Hefner paid $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.