Olyphant returned to television in 1998 for a guest starring role in an episode of the HBO sitcom "Sex and the City", playing a love interest for Carrie Bradshaw. Sarah Jessica Parker later said the episode, "Valley of the Twenty Something Guys", was her favorite of the series. 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.