Death to Smoochy
Jon Stewart's most beloved non–Daily Show foray (in our eyes) belongs to his performance as Marion Stokes, a corrupt children's-television executive in the cult classic Death to Smoochy. Alongside Edward Norton, Robin Williams and Danny DeVito, Stewart suited up for his villainous role as a greedy network exec in the middle of the unbelievably seedy world of children's entertainment. After firing the neurotic, crooked Rainbow Randolph (Williams), Stewart's character seeks out Smoochy, a tender rhino embodied by Sheldon Mopes (Norton), an idealist with high morals. (Stewart's character eventually orders a hit on Smoochy in the middle of an Ice Capades–like show.) Stewart's slimy suit act stands out as a cruelly perfect examination of the underbelly of kiddie entertainment.