Olyphant had a new outlook when choosing his 2009 projects, influenced by his experience with "Hitman": "It motivated me to take a little more responsibility with what I was doing ... I was very fond of the director and a lot of the people that worked on the film but there was definitely a part of me that was like, "What am I doing here?'" He starred as a morphine addict in the little-seen independent heist comedy "High Life", with Derek Elley of "Variety" praising his "terrific" performance. He had a starring role in the thriller "A Perfect Getaway" as a possible serial killer of fellow holidaymakers in Hawaii. Manohla Dargis of "The New York Times" enjoyed "the regrettably underemployed" actor's performance, Ty Burr of the "Boston Globe" found him "delightfully confident" while Lisa Schwarzbaum of "Entertainment Weekly" noted he "has a heckuva good time telegraphing macho mania." He was nominated for the Toronto Film Critics Association Award for Best Supporting Actor. He returned to the stage for one night to appear in "Standing on Ceremony: The Gay Marriage Plays", benefiting the Human Rights Campaign. Also in 2009, he appeared in 11 episodes of the FX legal thriller "Damages", as a morally ambiguous love interest for Rose Byrne's character. Byrne later said he was her favorite "Damages" guest star, while FX president John Landgraf sent him the pilot script for another FX project, "Lawman" (later renamed "Justified"). In 2010, he starred as the town sheriff in the horror film "The Crazies". Peter Bradshaw of "The Guardian" was impressed by the "saturnine screen presence of Timothy Olyphant – that formidable actor who deserves a lead role to match his potential." "The Hollywood Reporter"s Michael Rechtshaffen found him "convincing" while Claudia Puig of "USA Today" enjoyed the "smart, stoic and sympathetic" performance. He also appeared in the independent comedy "Elektra Luxx" (2010).