Big win: RJR Nabisco
Share gain: 83% (Reuters data)
Icahn hit headlines recently over high-profile stakes in Dell, Apple and Herbalife, but this is far from his first act of shareholder activism. His battle with the board of Oreos maker RJR Nabisco was notoriously long and bloody, and took most of the 1990s to resolve. Icahn's main aim was to separate the tobacco operation, which was at that point becoming increasingly vulnerable to lawsuits, from its food unit. When he eventually achieved his aim, he had made $1.3 billion in total, and Philip Morris paid $55 per share for Nabisco (without its tobacco operations), compared to the average $30 per share he bought it at (according to contemporaneous reports by the New York Times). Icahn's tenure at TWA, which ended in the august airline's bankruptcy, was notoriously less successful.
(Read more: Carl Icahn is 77. Big deal)