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Malkovich started his career as a charter member of the Steppenwolf Theatre Company in Chicago in 1976. He moved to New York City, acting in a Steppenwolf production of the Sam Shepard play True West (1980). He made his Broadway debut as Biff in the revival of the Arthur Miller play Death of a Salesman (1984). He directed the Harold Pinter play The Caretaker(1986) and acted in Lanford Wilson's Burn This(1987).

Malkovich has received two Academy Awards for Best Supporting Actor nominations for his performances in Places in the Heart (1984) and In the Line of Fire (1993). Other films include The Killing Fields (1984), Empire of the Sun (1987), Dangerous Liaisons (1988), Of Mice and Men (1992), Con Air (1997), Rounders (1998), Being John Malkovich (1999), Shadow of the Vampire (2000), Ripley's Game (2002), Johnny English (2003), Burn After Reading (2008), and Red (2010). He has also produced films such as Ghost World (2001), Juno (2007), and The Perks of Being a Wallflower (2012).

For his work on television, he received the Primetime Emmy Award for Outstanding Supporting Actor in a Limited Series or Movie for Death of a Salesman (1985). His other Emmy-nominated roles were for portraying Herman J. Mankiewicz in RKO 281 (1999) and Charles Talleyrand in Napoléon (2002). Other television roles include  Crossbones (2014), Billions (2018–19), The New Pope (2020), and Space Force (2020–2022).