He was a favorite of director Billy Wilder, starring in the films Some Like It Hot, The Apartment, Irma la Douce, The Fortune Cookie, Avanti!, The Front Page, and Buddy Buddy.
Postao je omiljeni glumac redatelja Billyja Wildera, nastupivši u glavnoj ulozi u njegovim filmovima Neki to vole vruće, Apartman, Slatka Irma, Kolačić sreće, Avanti!, Naslovna strana i Buddy Buddy.