In 1992, he began freelancing for Marvel Comics on various X-Men titles, then moving in 1994 to WildStorm, where he worked on a wide variety of titles, including the Brass mini-series.

In 1997, he did background and character design work for the first season of the animated Spawn HBO series.

A year later Bennett signed up to the full-time program at the Art Center College of Design in Pasadena.

In 2005 he became a member of the ADG Local 800 in Los Angeles, and has been steadily storyboarding mainly for films ever since, having collaborated with directors such as David Fincher, Christopher Nolan, Brad Bird and JJ Abrams among many others.

Some of the projects he hs worked on include Zodiac, The Curious Case of Benjamin Button, The Social Network, Star Trek, Mission Impossible: Ghost Protocol, Avengers, Captain America: Winter Soldier, Captain America: Civil War, Tron: Legacy, Dunkirk and Tenet.