Benjamin's style as a director relies on a strong use of mood and naturalism. He draws on experience from still photography, theater and his training in classical and jazz composition. Having studied music for years, rhythm and syncopation are crucial elements in his films. He has experience in the traditional advertising world with companies like Grey and Deutsch, as well as the music and indie film scenes. He's worked extensively in the US and Europe, most recently returning from 2 years in Berlin working in-house for the digital agency KKLD*. He has made films for BMW/MINI, Sundance Channel, Zac Posen, Virgin Atlantic and NIKE, among the others.
In 2007, Benjamin toured Europe with Lou Reed, directing the live show and a short film of the tour.
Benjamin's first narrative film, Tuscaloosa, was awarded Best Drama at the 2002 New York International Independent Film and Video Festival. The Comedian (2003) received a Boulder Media Award for Best Scripted Dramatic Work. In 2005, Mr. Flaherty was commissioned by Forum Theatre in Washington D.C. to direct a short film, Traces, which premiered during the staging of Ami Dayan’s Upshot. In 2010, Benjamin completed a short film entitled Wash.
As a writer, Benjamin's works for the stage include the use of space and rule the day, performed at the Rorschach Theatre and Forum Theatre respectively, both in D.C.
Most recently, Benjamin completed work on a series of films for BMW Project i, as well as the Cyndi Lauper DVD, To Memphis with Love.