Whitehead had a small, but important, role on “Friends,” playing Rachel’s boss, Mr. Waltham, in two episodes in Season Four. Rachel tasks Ross with going out with Mr. Waltham’s niece, Emily, and the two wind up falling in love, only for their romance to later go sideways when Ross says Rachel’s name at their wedding.
Whitehead also had a recurring role in another NBC comedy, playing uptight neighbor Hal Conway on “Mad About You.” He also made appearances on “The West Wing,” “Desperate Housewives,” “The Drew Carey Show,” “Ellen,” “The A-Team” and “Murder, She Wrote.”
Whitehead made his film debut playing snooty college professor Dr. Phillip Barbay in 1986’s “Back to School,” with his character often at odds with Rodney Dangerfield’s obnoxious and lovable Thornton Melon. He also starred in movies such as “Jumpin’ Jack Flash,” “Baby Boom” and “Kate & Leopold.”
Whitehead earned a Tony Award nomination in 1981 for his role as King Pellinore in “Camelot.” He would make 16 more appearances on Broadway, according to The Hollywood Reporter, including a run in “The Crucifer of Blood” from 1978 to 1979 that featured Glenn Close. That show would earn four Tony nominations.