Estes' break-out movie role was Seaman Ronald 'Rabbit' Parker on U-571. 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.
In 2000, according to a 2005 Soap Talk interview, Estes was asked by Jon Bon Jovi to be in his music video after he worked with Estes on U-571. Estes did most of his own stunts in the video.[5]
Estes had a leading role in the Fox series Reunion. The series followed six best friends over the course of 20 years, with each episode marking the next successive year. 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. He has also appeared in a couple of photographs, in the books Hollywood Splash and Men Before 10 AM Too. He was nominated four times for one award, the Young Artist Awards for The New Lassie and Kirk.
^Andreeva, Nellie (28 March 2005). "Will Estes is set to co-star opposite Michelle Trachtanberg in Lifetime's telefilm "Dive From Clausen's Pier."". Hollywood Reporter. Vol. 388, no. 23. Verenigde Nederlandse Uitgeverijen: Cengage. p. 14. ISSN0018-3660. GaleA131463580.
^"Squeegees". 15 February 2008. Archived from the original on 6 March 2016. Retrieved 29 June 2018 – via IMDb.