For me, choice is the most important thing because I'm going to be an adult actor pretty soon. So I've got to be choosing the right roles now so that by the time I get to that age there will be wide options available.

He appeared in the 1996 film Bogus alongside Whoopi Goldberg and Gérard Depardieu and the 1998 made-for-TV movie The Lake as well as I'll Remember April (1999) with future The Sixth Sense co-star Trevor Morgan. Asked to describe the biggest thing he had ever seen Osment described an IMAX theater screen and won the part in a Pizza Hut TV commercial advertising their "Big Foot" pizza. Osment was involved in a single-driver automobile accident on July 20 2006 in which he struck a brick mailbox and overturned his car while driving near his home.

He made his Broadway debut in 2008 in a short-lived revival of David Mamet's play American Buffalo starring John Leguizamo and Cedric the Entertainer. After a series of roles in television and film during the 1990s including a small part in Forrest Gump playing Tom Hanks' title character’s son Osment rose to fame with his performance as Cole Sear in M. Artificial Intelligence and Mimi Leder's Pay it Forward.