This deal led to the popular ABC series "Dharma & Greg,” a playfully romantic chronicle of an odd couple's happy marriage. Elfman played Dharma, the impossibly energetic and effervescent daughter of hippies who marries blueblood lawyer Greg (Thomas Gibson) in an act of spontaneity much to the chagrin of his ultra conservative parents. The likable sitcom was highly rated, and Elfman quickly emerged as the show's comedic crux, with Gibson's Greg playing handsome straight man. Elfman flourished on the series, and won much praise and publicity for this long-running high profile role. Happy with her small screen role and its success, Elfman nevertheless sought to expand her career to the arena of film. Her first role came in 1997, with a cameo in the acclaimed John Cusack black comedy, "Grosse Pointe Blank.” The actress followed up with a starring role as an obnoxious graduate student opposite Richard Dreyfuss in the comedy misfire "Krippendorf's Tribe" (1998). In the summer of 1998, Elfman had an uncredited cameo in the high school graduation party-set comedy "Can't Hardly Wait" as a straight-shooting stripper in the guise of an angel who advises a love struck teen (Ethan Embry). That same year, she voiced the owl in the remake of "Dr Dolittle,” starring Eddie Murphy.

In 1999, she made her starring feature debut opposite Matthew McConaughey in Ron Howard's "EDtv", a look at media frenzy, following a man (McConaughey) who agrees to have his life videotaped for a cable television station. Elfman played Ed's self-conscious love interest, a UPS worker who is uncomfortable with the constant camera presence. The actress was next featured in the marriage and midlife crisis-themed comedy "Town and Country", alongside Warren Beatty and Diane Keaton, and appeared in the triangular romance "Keeping the Faith" (both 2000), Edward Norton's directorial debut which starred Norton and fellow actor-director Ben Stiller as a priest and a rabbi respectively who become rivals for Elfman's love. Additionally, the actress practiced her craft on stage opposite Miguel Ferrer in the acclaimed "Visions and Lovers,” staged by her acting teacher Milton Katselas. Elfman displayed a gift for dramatic acting on par with her comedic chops in Lifetime's "he said-she said" telepic "Obsessed" (2002), playing a seemingly clever and charming woman who insists she had a torrid one-night stand with a prominent doctor (Sam Robards), only to have gradually unveiled facts shed new light on her story. She followed that with a high-profile turn as a Warner Brothers studio exec who makes the grievous error of firing Daffy Duck in the animated/live-action hybrid "Looney Tunes: Back In Action" (2003).

Elfman was next seen on a couple episodes of “Two and a Half Men” (CBS, 2003- ) as a seemingly crazy woman for whom Charlie falls, then provided the voice of Dorothy in “Clifford’s Really Big Movie” (2004), an animated feature based on Norman Bridwell’s series of children’s books, “Clifford the Big Red Dog.” Elfman returned to regular series work with a new sitcom, “Courting Alex” (CBS, 2005- ), a midseason pickup in which she played a single, straight-laced Manhattan attorney trying to balance work and her relationships with the various men in her life. Also serving as producer, Elfman spent nearly two years developing the show and held considerable sway over all facets of production—including casting, set design and wardrobe—so she could lay claim to what she felt was a unique and original show. Despite receiving mixed reviews, “Courting Alex” opened to descent ratings and held a steady audience through the first part of 2006.