Robert Downey Jr., Charlie Sheen, and Sean Penn were all buddies while attending Santa Monica High School together in the early ’80s. While Downey Jr. and Sheen have had their fair share of bad press and stints in rehab, Downey Jr. seems to have come out on top with a strong career comeback as the hit Marvel superhero Iron Man. Sheen, however, hasn’t been “winning” as much lately since his abrupt departure from the hit sitcom Two and a Half Men.