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Além de seu papel de destaque em The Office, Wilson tem interpretado o excêntrico Arthur Martin, na série da HBO Six Feet Under. Já apareceu também nas séries CSI, NUMB3RS, e Entourage. Wilson co-estrelou um episódio da ´série Monk como um fã-assassino de baseball. Sua filmografia inclui filmes como Almost Famous, America's Sweethearts, BAADASSSSS!, Galaxy Quest, House of 1000 Corpses, Sahara e The Last Mimzy. Ele apareceu ao lado de Luke Wilson e de Uma Thurman no filme My Super Ex-Girlfriend. Também apareceu num episódio de Charmed como um alquimista de nome Kierkan. Em 24 de fevereiro de 2007, Wilson apresentou o Saturday Night Live, se tornando o segundo membro do elenco de The Office a apresentar o programa, após Steve Carell. Ele participou do filme de 2007 "Juno" no papel de Rollo, o dono de uma farmácia.
O próximo papel de Wilson será no filme The Rocker, previsto para 2008. Também esperado para 2008 é o filme Bonzai Shadowhands, co-escrito e co-produzido pelo ator. Além disso, Wilson escreveu e está co-produzindo Renaissance Men, cujo lançamento é previsto para 2010.
Wilson tem um blog no site da emissora norte-americana NBC chamado "Schrute-Space" (O Espaço de Schrute), no qual ele escreve na pessoa de Dwight.
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