Superman #146

The cover of Superman #146 (July 1999) transforms the Man of Steel's greatest struggles into a darkly clever board game called "The Superman Game," complete with dice, a deck of Kryptonite Cards, and game-piece robots blasting him with energy beams as he fights back across the colorful board. Spaces bearing grim instructions like "Death Trap!!!", "Doomsday Attacks! Go Back Three Spaces!", and "Metropolis Burns!" make it bracingly clear that Superman's life is anything but easy. Cover artists Dan Jurgens and Joe Rubinstein bring real wit and energy to the concept, and the "Play at Your Own Risk!" warning feels entirely earned.