Dark-haired and quick witted, with a winning smile and a mischievous allure, Brewster broke through as a talk show host on the aptly named late-night series "The Paget Show", aired on San Francisco's KPIX. Fielding topics that ranged from serious family disputes to drag queen makeovers, she had a likable, spunky presence and came across well in the genre. The series was courted by syndication companies, the USA Network and Fox, but despite this interest, and no doubt partly due to the influx of other talkers on the air at the time, "The Paget Show" never lived past its 65 episode KPIX incarnation.
Still, her engaging energetic presence opened doors for acting opportunities, and she filmed two failed sitcom pilots for Fox, the music video network-set "MV24" and a zany vehicle for comedian Dana Gould entitled "World on a String". Persevering despite these early disappointments, Brewster landed a role on the popular NBC sitcom "Friends", playing Kathy, a medical assistant/actress who dates hunky but dim Joey, only to fall in love with his sarcastic, self-effacing roommate Chandler. Brewster appeared on six episodes of the series, significantly raising her profile and lining up more starring roles in failed pilots, including the Fox police series "Ghost Cop" and the CBS detective drama "The Expert". 1998 saw her take on a recurring voice role in the Fox animated adventure adaptation "Godzilla: The Series" and a starring role as a NASA technician in the action packed "Max Q" (ABC), producer Jerry Bruckheimer's misfired TV-movie debut. Brewster struck gold with "Love & Money", a CBS pilot picked up for the 1999 fall season, in which she starred as Allison Conklin, a kindergarten teacher and daughter of privilege who falls for her affluent apartment building's blue-collar superintendent (Brian Van Holt). With a supporting cast including Swoosie Kurtz as her boozy mother and David Ogden Stiers as her austere father, she made her network television starring debut in good company and considered the series, whether or not it proved a hit, an invaluable learning experience.
On the big screen, Brewster starred in the 1998 independent feature "Let's Talk About Sex", as Michelle, an intimacy-wary and controlling single woman who routinely dates much younger men. She could also been seen that year as a movie star who holds a contest to find a boyfriend in the festival screened independent "Skippy". Brewster played a fast-talking down-on-her luck actress in Bill Fishman's "Desperate But Not Serious" (lensed 1998), co-starring Christine Taylor and Claudia Schiffer and was later featured in "The Specials" (lensed 1998) as Ms. Indestructible, comprising, along with actors including Rob Lowe and Thomas Haden Church, a group of oddly powered superheroes in this "Mystery Men" (1999) reminiscent comedy.