Though her role as 'Stoned Girl' in the teen comedy "Can't Hardly Wait" was drastically cut to earn a PG-13 rating, Benson soon became a familiar presence to the film's target audience when she began appearing on "Buffy the Vampire Slayer" (The WB) the following year. Her 1999-2001 recurring role as the good witch who becomes more than just a friend to fellow enchantress Willow (Alyson Hannigan) saw the actress taking on controversial topics and earning the esteem of the notoriously hard-to-please "Buffy" fan base. When the series moved to UPN in 2001, Benson's role was upgraded to that of a regular. In connection with "Buffy", the actress sought to broaden the scope of her talents, co-writing with novelist Christopher Golden the comic book WannaBlessedBe, based on her character on the supernatural series.

Back on the big screen, Benson was featured in the festival-screened, controversy-plagued "Don's Plum" (2001; filmed 1995-96) which was barred from domestic release as per a legal agreement mandated by the film's stars Leonardo DiCaprio and Tobey Maguire, who allege the project was misrepresented. Taking over her own project, Benson proved a multitalented filmmaker and avid do-it-yourselfer as writer, producer, director and prime financer of "Chance" (lensed 2001), a dark comedy in which she also starred.