Though Chicago native Matt O'Leary got plenty of screen time as a pre-teen murder witness in thriller director Harold Becker's underwhelming 2001 box-office disaster, "Domestic Disturbance," and as Gary Giggles, the spiky-haired son of comedian Mike Judge's incomprehensible Donaggon Giggles in two installments of Robert Rodriguez's family-friendly action franchise "Spy Kids," it wasn't until his transition to smaller, independent projects that he truly came into his own. In 2005, he appeared with Oughties breakout star Joseph Gordon-Levitt as a supporting player in documentarian Barbara Kopple's gripping narrative feature "Havoc," a cautionary tale about culture clash and gang violence set in seedy downtown Los Angeles. The duo worked together again when O'Leary played The Brain, the fast-talking sidekick to vengeful boyfriend Brendan (Joseph-Gordon Levitt) in Rian Johnson's boldly original high school neo-noir "Brick" (2005). O'Leary was praised for his frenetic and engaging performance, and began taking on more unusual roles. Where "Brick" proved he was a compelling character actor, his depiction of an invitro-fertilized meth-head in "Natural Selection" (2010)--first-time director Robbie Pickering's award-winning indie sperm-donation satire--revealed the true depth and maturity of his capabilities. O'Leary and his co-star, the long-underrated commediene Rachael Harris, shared the award for Breakthrough Performance at South by Southwest in 2011.