Olyphant's first post-"Deadwood" roles were the action movies "Live Free or Die Hard" and "Hitman" (both 2007). ("Coastlines" was first screened during the Sundance Film Festival in 2002 while "Catch and Release" was filmed in 2005.) He had bought a house in the weeks before "Deadwood"s cancellation and he later admitted his job choices during this period were for "purely financial reasons." In "Live Free or Die Hard", he played a villainous cybersecurity expert. Both he and Bruce Willis have said his role was underwritten in the script, and he enjoyed working with Willis to develop the character. Peter Travers of "Rolling Stone" declared him "a master at smiling menace", while Mick LaSalle of "The San Francisco Chronicle" found him "perfectly ice cold." However, Manohla Dargis of "The New York Times" remarked: "Mr. Olyphant has many charms, but annihilating menace is not one of them." He next starred in "Hitman", a video game adaptation, as the assassin Agent 47. He was hired to replace Vin Diesel six weeks before filming began and reluctantly agreed to shave his head. The film was commercially successful, grossing over $100 million, but received negative reviews. Todd McCarthy of "Variety" described Olyphant as "an actor capable of portraying subtle ambiguities and thought, which suggests he ought to branch out to play something other than baddies." Nick Schager of "Slant Magazine" was disappointed to see the actor "reduced to glowering and posing with pistols" while Manohla Dargis of "The New York Times" felt he was "strangely, at times ridiculously, miscast." In 2008, he had a supporting role as a Lieutenant Colonel in the Iraq War drama "Stop-Loss", played a pompous newscaster in the little-seen comedy "Meet Bill", voiced the character Cowboy in the video game "Turok" and made a guest appearance on the first season of the ABC sitcom "Samantha Who?" with Christina Applegate.