The self-referential "Scream" (1996), a witty film both parodying and celebrating the conventions of horror movies would prove to be Williamson's big break. Directed by horror maven Wes Craven and starring a cast primarily made up of new faces, the film breathed a hip, fresh life into the dying teen slasher genre. For his next blockbuster, "I Know What You Did Last Summer" (1997), Williamson adapted the Lois Duncan novel of the same name (a perennial junior high favorite). While his screenplay was essentially a complete overhaul, the film maintained the original psycho-thriller tone, even while adding more of a horror movie sense than was in the text. Seeking to create a new Michael Myers-esque villain, he made the antagonist a mysterious fisherman, creating a new urban legend. Later that same year, the action-packed "Scream 2" proved a comparable success, resulting in the final follow-up ,Scream 3" (2000), which Williamson produced but did not script. Following the strong box office returns for the Williamson scripted "Scream", "I Know What You Did Last Summer" and "Scream 2", a resurgence of movies starring and aimed at teens hit the big screen, typically employing relatively affordable young film and TV actors in inexpensive, easily produced horror fare usually with big opening weekends .

Williamson next served as executive producer of "Halloween: H20", the seventh installment of the series, and arguably the only sequel that lives up to John Carpenter's terrifying 1978 original. This film brought back legendary scream queen Jamie Lee Curtis, and introduced new kids Michelle Williams (of "Dawson's Creek) and Josh Hartnett (of the Williamson-scripted "The Faculty"), bringing the new class together with horror movie royalty, something that Williamson had done thematically with his previous films. With "The Faculty" (also 1998), the screenwriter set out to fuse a "Breakfast Club" element of disparate stereotypes thrown together with an "Invasion of the Body Snatchers" plot line. The result, directed by Robert Rodriguez, was a highly entertaining rollercoaster ride of a film.

Williamson's screenplay for "Killing Mrs. Tingle", a black comedy thriller inspired by his own real-life experience with a discouraging teacher, was initially picked up for development by Interscope, but put on hold. Following his "Scream" success, the film was reclaimed by Dimension Films, Miramax's genre division, with Williamson not only on board as screenwriter, but making his debut as director. Released in the summer of 1999 as "Teaching Mrs. Tingle", it starred Helen Mirren, Katie Holmes ("Dawson's Creek") and up-and coming Williamson discovery Marisa Coughlan ("Wasteland"). After a lengthy absence from the big screen while developing his TV projects, Williamson reteamed with Craven for the werewolf thriller "Cursed" (2005).

While carrying on a fruitful and acclaimed film career, Williamson managed to create the TV series "Dawson's Creek", and keep it fresh and compelling past its first season. A sensitive and intelligent coming-of-age drama populated with realistic (if unusually eloquent) characters, "Dawson's Creek" introduced an ensemble of uniquely talented and watchable new faces and proved an instant success, making immediate teen idols out of the principal cast (the aforementioned Holmes and Williams as well as James Van Der Beek and Joshua Jackson). A semi-autobiographical program, Williamson has said hat each character in the series distinctly represents various aspects of himself. Next up for the self-described workaholic was "Wasteland", a Miramax/Kevin Williamson production chronicling six young college graduates and their exploits in New York that failed to find an audience during its brief run in the fall of 1999. He returned to series TV with the well-reviewed but equally short-lived "Glory Days" (2002), centering on a mystery novelist who returns to his home town to discover the natives are mysteriously unnerved by his use of their community in his work.