Early in his career, he did many commercials including Fruit of the Loom and numerous guest starring roles in series like Highway to Heaven and Santa Barbara.

When the group meets up for its 20th high school reunion, one turns up dead at the end of the night.

In late 2005, Fox announced that the series would be canceled because of low ratings and the identity of the murderer would not be revealed.

Estes portrayed Jack Kerouac in the 2007 short film Luz Del Mundo, written by Ty Roberts and David Trimble, directed by Ty Roberts, and produced by Ryan McWhirter and John Pitts.

Since 2010, Estes has been playing Jamie Reagan in the police procedural television series Blue Bloods.