Sergei returned to feature work with a role in the 1997 independent western "Gunfighter's Moon", an international theatrical release that went direct-to-video in the USA. The following year he essayed the role a slow-witted hunk seduced by the manipulative half-sister (Christina Ricci) of his partner (Martin Donovan) in Don Roos' acclaimed independent black comedy "The Opposite of Sex". Beginning in 1999, he reached a wider audience with a starring role on the romantic comedy "Jack & Jill" as David 'Jill' Jillefsky, an awkward but charming toy designer who falls for his affianced neighbor in New York City. During the series' 1999-2001 run, the actor completed several independent films including 2000's "Playing Mona Lisa". In 2002, he returned to series television with the ABC midseason replacement "Wednesday 8:30 (9:30 Central)", a sitcom set in the world of network television.