Like Harry Potter's Daniel Radcliffe, Osment attempted to change his image and transition to adult roles by performing on Broadway. Unlike Radcliffe's Equus, Osment's play, American Buffalo only ran for a week, opening on November 17, 2008 and closing on November 23, 2008.Backstage: American Buffalo to Close (November 19, 2008)

• Osmet made his Broadway debut in American Buffalo, the story of three men in a junk shop who plan to steal a rare nickel. The show premiered on November 17, 2008 but due to poor reviews and a depressed economy, it was announced the show will close on November 23, 2008. The cast included John Leguizamo and Cedric the Entertainer and was directed by Tony-winner Robert Falls.Theater Mania: American Buffalo Posts Provisional Closing Notice (November 19, 2008)

• '"My friends are definitely more important than my career. If I had to choose, I'd choose my friends over my career."
• "Being different personalities brings out some of the personalities that you have, too. So I guess I have become a more well-rounded person."
• "It's important in selecting films that have that feeling behind them, there's a place for films that are just light and entertaining, but for me it's most important to find the films that will last."
• "It makes me feel great when other young actors say they look up to me. I hope I can be a positive role model."