Perhaps the best known guest star in Roseanne's history, George Clooney actually got his start a few years earlier on the Facts of Life. This led to his appearance as Booker and eventually to the role that made him famous today - as Dr. Doug Ross on ER. But Clooney's role on Roseanne - though brief and minimal - was actually more than just a guest spot. The character of Booker Brooks was both Roseanne's boss, friend, and her sister Jackie's one-time boyfriend. Despite disappearing early in the series' run the character of Booker was quite important for such a small role. Clooney - of course - went on to become one of the biggest names in Hollywood far outshining his former costars. George has gone on to star in many famous flicks including the Ocean's series, and O Brother Where Art Thou which reunited him with Roseanne costar John Goodman. He played the final incarnation of Batman before Christopher Nolan reinvented the character, and in the last ten years has been nominated for eight Academy Awards winning two - one each for his acting and producing capabilities. Clooney has proven himself to be far more than just a handsome face and has continued to wow audiences with his recent performance in ten-time Academy Award nominee Gravity. Still, Clooney shows no sign of slowing down with upcoming projects for both 2014 and 2015.