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Conhecido principalmente por atuar na série American Pie, fazendo o papel de Steve Stifler, sendo um grande sucesso.
Recebeu uma indicação ao MTV Movie Awards de melhor equipe, por Os Gatões - Uma Nova Balada, com Johnny Knoxville.
Ganhou o MTV Movie Awards de Melhor Beijo, por American Pie 2, com o ator Jason Biggs.
Recebeu uma indicação ao MTV Movie Awards de Melhor Comediante, por American Pie 2.
Ganhou o MTV Movie Awards de Melhor Sequência de Dança, por American Pie - O Casamento.
Atuou ainda ao lado dos atores Ashton Kutcher, em Cara, cadê meu carro? , The Rock em Bem Vindo à Selva , Billy Bob Thornton em Em Pé de Guerra e dublou uma das vozes do filme A era do gelo 2 e Planet 51.
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