Often bespectacled and projecting a slightly nebbishy air, Malina has been able to play a variety of ethnicities and religions. Early in his career, in addition to the Sorkin-scripted projects, he landed small roles in independent features (i.e., the receptionist in "Clockwatchers" 1997). Warren Beatty tapped him to portray a harried campaign worker in "Bulworth" (1998) before he landed his biggest film role to date, as co-star with Luck Wilson of the Sundance-screened comedy "Kill the Man" (1999). In 2002 Malina again reunited with Sorkin to play "The West Wing's" Will Bailey, a California campaign manager who lures Sam Seaborn (Rob Lowe) into taking a congressional seat won by a deceased candidate; Malina later stepped into Lowe's vacant slot on the acclaimed series and became a regular cast member when his character took a job as a presidential speech writer.