In 2009, he starred in the Independent Spirit Award-winning film Humpday, for which he won Best Actor at the Gijón International Film Festival. Leonard has also appeared on the acclaimed HBO series Hung and the Showtime series United States of Tara. Leonard directed the short film The Youth in Us, which was shown at the 2005 Sundance Film Festival. Art documentary Beautiful Losers followed, winning the Grand Jury Prize at CineVegas in 2008. He has also directed music videos for many popular acts, such as Morcheeba, Harper Simon, and Fitz and the Tantrums, as well as teaching directing and acting at The New York Film Academy, UC Irvine, and Academia Internacional De Cinema in São Paulo, Brazil. In 2011, Leonard starred in Vera Farmiga's directorial debut drama film Higher Ground, playing a religious man at odds with his wife (Farmiga). He also co-wrote, directed and starred in The Lie, a devilish morality tale adapted from the story by acclaimed author T. C. Boyle. The project co-starred Mark Webber, Jess Weixler, and Jane Adams, and was well received by audiences and critics.