Following a turn as a college football player accused of harassment in the NBC movie "Silencing Mary" (1998), Hopkins portrayed Microsoft co-founder Paul Allen in the TNT original "Pirates of Silicon Valley" (1999). Next, he scored a recurring role as a potential rival for the heroine's hand in the romantic comedy-drama "Jack & Jill" (The WB). For several episodes that aired in 2000, Hopkins played Matt Prophet, a TV newscaster who romanced Amanda Peet's Jacqueline 'Jack' Barrett much to the consternation of Ivan Sergei's David 'Jill' Jillefsky. Later that year, the actor had a small role as a helicopter rescuer in "The Perfect Storm", a part that was overshadowed by the special effects and somewhat confusing editing. Hopkins was seen to much better effect as an egotistical actor who falls for a journalist (Famke Janssen) in the sprightly romantic comedy "Love & Sex". He was also tapped for a featured role in the John Woo-directed "Windtalkers" (2002).
Hopkins was set to return to the small screen as a private investigator hired to track the woman with whom he was having an affair in a Fox series titled "Fling" but the network pulled the plug on production after only seven episodes. Instead, the actor was asked to join the cast of the long-running Fox series "Ally McBeal" beginning in the fall of 2001, playing attorney Raymond Millbury, a potential love interest for the title character.