His first role was on the soap opera The Edge of Night, and one of his first movie starring roles was in Shaft (1971). His other film credits include Making It (1971), The Crazy World of Julius Vrooder (1974), The Man in the Glass Booth (1975), 9 to 5 (1980), The Hanoi Hilton (1987), Angus (1995), Trial and Error (1997), Very Bad Things (1998), Mighty Joe Young (1998) and American Pie (1999). He played Col. Cathcart in the Hanoi Hilton.
Pressman played Bill Denton in the 1976 miniseries Rich Man, Poor Man. He portrayed H. R. Haldeman in the 1979 CBS miniseries Blind Ambition, and also appeared in the 1983 miniseries The Winds of War.
