Dillman began his Broadway stint as Edmund Tyrone in Eugene O’Neil’s play “Long Day’s Journey into Night” in 1956. He played the role for 390 performances and won a Theater World Award for his portrayal in 1957. He also starred in Katharine Cornell’s production of “There Shall Be No Night.” He then transitioned to film and signed a contract with 20th Century Fox. He was awarded a Golden Globe for most promising newcomer – male, for his role in “A Certain Smile,” before taking on a series of darker roles.
He shared the 1959 Cannes Film Festival Award for best actor with co-stars Orson Welles and Dean Stockwell for his work as Arthur A. Straus in “Compulsion.” Among his other appearances were “Sudden Impact” with Clint Eastwood and “The Way We Were” with