As author of the popular Los Angeles plays "Pay or Play" and "d girl" (1997) Kumble poked fun at the Hollywood system by showing its darker side and exposing the competitive and opportunistic drive behind many a success story. "Pay or Play" starred Jonathan Silverman and Dana Ashbrook as twentysomething executives looking for a hit, while "d girl", the story of a young newly appointed director of development who discovers that one must swim with sharks to make it, starred David Schwimmer. Somewhat mean-spirited, Kumble's satires proved so dead on that they became very hot properties, so much so that the very studio bigwigs he was mocking were clamoring for tickets to the small-capacity productions.

While Kumble's stage work was very well-received and earned the writer notice and nods from L.A. Weekly and Drama-Logue, his early film work was less remarkable. As a contributor to the Farrelly comedies "Dumb & Dumber" (1994) and "Kingpin" (1996), his writing went uncredited, and while he had a hand in 1995's formulaic "Mighty Morphin Power Rangers", his name was not connected to the film. Screenplays written by and credited to Kumble proved less successful and included the direct-to-video erotic thriller "Unveiled" (1994) and the equally uninspired spy film "Provocateur" (1998), starring Jane March. He also wrote "National Lampoon's Senior Trip" (1995), a Washington DC set fast-paced comedy that had some laughs, but failed to generate any real notice or box office returns.

With no screen directing credits, Kumble sought to make an independent film adaptation of the classic novel "Les Liaisons Dangereuses" set in high school, noting teens as the perfect purveyors of manipulative inhumanity following a screening of Todd Solondz's portrait of middle school cruelty "Welcome to the Dollhouse" (1995). He planned it to be a low-budget production, but the project was picked up by producer Neal H. Moritz, who had achieved teen movie success with "I Know What You Did Last Summer" (1997) and its 1998 sequel. Given a much larger budget than anticipated, Kumble was allotted more freedom and was able to attract a bigger name cast. "Cruel Intentions" mirrored the somewhat bitter spirit of his plays, this time harnessed as a viciousness all too familiar to high school students. The story of New York City based children of privilege who sexually and emotionally manipulate those who cross their path surprisingly proved an enjoyable ride. Despite their abhorrent actions, Kumble's characters were inexplicably likable, and their portrayals flirted engagingly on the edge of campiness. Casting hot properties Sarah Michelle Gellar and Ryan Phillippe as leads helped to win a solid teen audience, and while the film was sexually descriptive enough to warrant its R rating, it was not very visually explicit, featuring negligible nudity. In a bold move, Fox ordered a TV pilot based on the film before it was even released. "Manchester Prep", the television series prequel to the film was written and directed by Kumble, who additionally served as executive producer. It never aired, however, after the network withdrew its support.

Kumble followed his "Cruel Intentions" success with the screenplay for "Gossip" (2000), a college-set psychological thriller starring a who's who ensemble cast of up and coming Hollywood. His next feature writing and directing project would come with an as yet untitled Columbia Pictures film based on a NEW YORK magazine expose of a pair of publicists who reinvented a saleswoman as a hot socialite, only to have their manipulative game backfire.