Also that year, he had supporting roles in the HBO war film When Trumpets Fade and the independent ensemble drama 1999. Two little-seen films were released in 1999: the drama Advice from a Caterpillar, in which Olyphant played the bisexual love interest of Cynthia Nixon's character, and the offbeat ensemble comedy No Vacancy, in which he starred with Christina Ricci. Olyphant received positive notices for portraying a drug dealer in the cult comedy Go (1999). Janet Maslin of The New York Times noted that the role was "played with offbeat flair" while Todd McCarthy of Variety described it as a "deftly etched" performance. He was set to star in the fantasy film Practical Magic, but he was replaced by Aidan Quinn. After Olyphant's performance in Go, the film's producer Mickey Liddell offered him his choice of parts in his next project The Broken Hearts Club (2000), a romantic comedy about a group of gay friends living in West Hollywood. The Village Voices Dennis Lim commented that his leading performance was better than the film deserved: "Olyphant is charismatic enough for his worst lines not to stick." However, Mick LaSalle of the San Francisco Chronicle felt he played the part "like a straight actor gaying it up." Olyphant played a detective in the successful action film Gone in 60 Seconds (2000) and joked in an interview about the challenges of playing "second fiddle to a car"; his performance reminded the Washington Posts Stephen Hunter of a young Bill Paxton. Olyphant was offered a starring role for a character called Dominic Toretto in another car film called Redline – that would later be retitled The Fast and the Furious. According to Sony producer Neal H. Moritz, "The studio said, 'If you can get Timothy Olyphant to play that role we will greenlight the movie.'" Olyphant declined the role, which went to Vin Diesel. The film went on to be a massive success with eight sequels to date. Olyphant later discussed passing on a lot of roles earlier in his career. In 2011, when asked by The Hollywood Reporter what was the most absurd project he had ever been pitched, he replied, "I've passed on absurd projects and they have become enormous, enormous hits spawning numerous sequels, and I'm not in them." In 2018, he reflected on passing on the role of Toretto in The Fast and the Furious, thinking it would be