Jonathan made his acting debut in the 1993 TV drama Family Passions. Finally, in 1994, he landed his breakthrough role as R.J Winslow in the Canadian teen drama Madison. He returned to the medical drama series Er from 1997 to 2001. He has also appeared as a guest star in a number of series, including The L Word, NYPD Blue, CSI: Miami, and Grimm.
Jonathan has also appeared in films such as The Work and Glory (2004), Joseph Smith (2005), Radio Free Albemuth (2010), and many others. He is now seen in The Equalizer. Among his other significant films and television programs are Raising the Bar, Hell on Wheels, Van Helsing, Ties That Bind, Doubt, 100 Days in the Jungle, and White Lies.