Every Main West Wing Character Ranked From Worst To Best

Will Bailey (Joshua Malina) is the embodiment of an Aaron Sorkin character. As he shared in Los Angeles Magazine, Malina appeared in the Broadway series "A Few Good Men," written by Sorkin, and Sorkin's previous television series, "Sports Night." When he heard rumors that Rob Lowe was leaving "The West Wing", he called his former collaborator and offered him "a lesser-known, less good-looking actor willing to work for a lot less money" as his replacement. Sorkin agreed immediately and began writing Will Bailey in action.

While Malina fit right in with the cast, quickly gaining a reputation as a prankster on set, her character has come down a much tougher path. After running a successful congressional campaign for a deceased candidate, Will takes over as Bartlet's assistant director of communications. He is thrown into the fire almost immediately, attending the State of the Union speech helping Toby beat a bad case of writer's block.

Will would likely rank much higher on this list were it not for his Season 5 stint in enemy territory. Leaving Bartlet's office, he becomes the chief of staff to "Bingo" Bob Russell (Gary Cole), a substitute vice president that no one takes seriously. This turns into a presidential campaign that pits Will directly against Josh Lyman and his candidate, Matt Santos, which has reportedly drawn animosity from fans of the show. Had he ventured down a different path, Will would be a standout on the show. As it stands, he too often seems to fill a void left by other characters, rarely getting a chance to shine on his own.