The son of a theater professor, Leonard was raised in State College, Pennsylvania. As a six-year-old, he was shanghaied by his dad into appearing in plays like "Life With Father". By the time he hit puberty, though, Leonard had decided that acting "was the last thing I wanted to do with my life." Instead, he pushed to obtain his GED at age 16 and underwent survival training with Outward Bound as preparation for a year and a half stay in Mexico where he volunteered with a youth services organization. After teaching poor children in Puebla, working as a gardener and hiking through the jungles of Central and South America, Leonard headed home to spend a year at Penn State. Growing restless, he opted instead to head to Manhattan and try his luck as a filmmaker and photographer.
In the Big Apple, Leonard found work taking portraits of musicians, toiled as a band promoter, acted in the occasional student film and worked as in various production capacities on shorts and documentaries. In 1998, he auditioned for and landed one of the three principal roles in an experimental independent feature that turned out to be "The Blair Witch Project". Although he reportedly only earned an initial salary of $500, the experience proved rewarding in other ways as the mock documentary shot in "extreme realism" combined his twin loves of acting and photography. After the midnight screening at Sundance and the subsequent hype, Leonard and his co-stars found themselves in the enviable position of being in demand. (Appearing on the cover of Newsweek also didn't hurt.) He accepted a number of acting roles and remained busy, surfacing in "Sacrifice" (aired on HBO), starring Michael Madsen and Bokeem Woodbine, and starring as a struggling playwright and moral center of "In the Weeds" (both 2000), a cliche-transcending look behind a high-powered midtown Manhattan restaurant, boasting outstanding performances by the likes of Eric Bogosian (as the restaurant's sadistic owner) and Molly Ringwald (as the fragile veteran waitress Chloe). Leonard made his first appearance in a studio film supporting Cuba Gooding, Jr in "Men of Honor" (2000), the story of the first African-American Navy diver Carl Brashear, and followed with Scott Kalvert's "Deuces Wild" (2001), executive produced by Martin Scorsese.