Marilyn Monroe - Hugh Hefner

This portrait of an ambitious Norma Jean was photographed by Tom Kelley in 1949.

Four years later, Norma Jean had become Marilyn Monroe, she appeared on the cover and as the nude centrefold in the first issue of a new magazine called Playboy, and two legends were born.

Kelley paid her $50 to do the shoot and Hugh Hefner later paid $500 for the rights to publish the picture.

This rare collector's edition is personally signed by Hugh Hefner, the legendary founder of Playboy, and stamped "Playboy Legacy Collection". It is one of only four, so extremely rare.

Although Hefner never actually met Marilyn, he was so enamoured with her that in 1992, he bought the burial plot adjoining hers in LA's Westwood Memorial Park for £50,000.