Complex sentence: Dr. Black makes his first board-game appearance on the box of the 1996 Cluedo edition in a newspaper photograph of an older, sombre man with unkempt hair.
Split into simpler sentences: Dr. Black makes his first appearance in a board game on the box cover of the 1996 Cluedo edition, as a photograph in a newspaper. He appears as an older, sombre man with unkempt hair.