In 2002, following the cancellation of The Associates he was cast in the legal drama series Just Cause, which ran for one season.
Benson played the recurring role of Dr. Steven Lars Webber on the soap opera General Hospital from 2004 to 2005, which attracted him considerable attention compared to his previous roles. Since his time on General Hospital, Benson has guest starred in numerous television series, including Cold Case, The Unit, and Being Erica.
In 2012, Benson starred in the IMAX 3D documentary film Flight of the Butterflies and in French comedy Populaire.
In 2013 Benson directed Stop Kiss for the Toronto Fringe Festival. The production had a sold out run which was extended as a result of winning Best of Fringe honours.
In 2014, Benson directed the independent film Barn Wedding, which won the HMV People's Pick For Best Flick award at the 2015 Canadian Film Fest.
In the 2015 made-for-TV movie Kept Woman Shaun played an eccentric professor, Simon, who kidnaps his neighbor Jessica, played by Courtney Ford. Also in 2015, he starred in the Starz television series The Girlfriend Experience, alongside Riley Keogh.
In 2016 Benson appeared in the Netflix time loop thriller ARQ as Sonny, as well as Season 2 of the series Gangland Undercover as Crowbar. He subsequently appeared in the SyFy series Channel Zero as the town sheriff, Gary Yolen.
