Silverstone went on to play Jeff Goldblum's imperiled daughter in "Hideaway" (1995), a supernatural flop. She had fared better on the small screen in "The Cool and the Crazy" (1994), a Ralph Bakshi-directed installment of Showtime's "Rebel Highway" telefilm series, playing a troubled young bride. Silverstone returned to the big screen for Amy Heckerling's "Clueless" (1995), a critical and commercial success perhaps best described as a "Fast Times at Ridgemont High" spin on Jane Austen's "Emma". Silverstone displayed a penchant for character-driven comedy as an affluent teen who comes to question her values, a role which fit her like a glove. Her adroit performance skyrocketed her value, and the season's "It-Girl" subsequently signed a deal worth between $7 and 10 million to produce and star in two movies for Columbia Pictures. Furthermore, the savvy teenager snared a three-year non-exclusive "first-look" production pact with the studio for her production company, First Kiss Productions.

Silverstone's next two projects, "Batman & Robin" and "Excess Baggage" (both 1997), took some of the luster off the golden girl. Two years between projects had left the press with little to do but snipe at her purported weight gain, laying it on thick with the "Fatgirl" (or worse "Buttgirl") and "Excess Baggage" jokes, which Silverstone took in stride. What was harder to take was the out-and-out failure of both films. She had little connection with the "Batman" debacle beyond her miscasting and presence at the train wreck. But "Excess Baggage", the first offering of her production company, was a hopelessly muddled product of seven screenwriters (not all credited) that suffered simultaneously from too much control and not enough control on the part of Silverstone, leaving her career (and company) in need of a very good outing next time around.

Unfortunately, she opted for the pallid romantic comedy "Blast From the Past" (1999) opposite Brendan Fraser. Although on paper the project appeared to have possibilities (he's lived his whole life in an underground fallout shelter, she's the contemporary chick who introduces him to the ways of the world), the final execution left reviewers and audiences bored. Silverstone fared much better in an unlikely role, her first Shakespearean part in "Love's Labour's Lost" (2000), Kenneth Branagh's musical take on the Bard's romantic comedy. While some found his homage to the musical films of the 1930s and 40s a bit much, most were entranced by the leading lady. Silverstone also exhibited her sweet, if untrained, vocal ability in the film.

An avowed vegan with strong socio-politiical views on animals rights, Silverstone soon spent much of her time promoting animal friendly causes, including lending her voice to 13-year-old Sharon Spitz, the lead character of the socially conscious and frequently awarded animated TV series "Braceface" (2001-2003), which the actress also executive produced. On screen, Silverstone's 2002 heist comedy "Scorched" and rock satire "Global Heresy" made little impact, but that same year she received many positive critical notices for her stint on Broadway as Elaine Robinson in the popular stage production of the classic 1967 film "The Graduate," opposite Jason Biggs and Kathleen Turner. By then Silverstone was prime for a major comeback, but this time the medium would be the small screen. She teamed with hot producer Darren Star ("Melrose Place," "Sex in the City") in a repeat of the formula that Star was so successful with when he teamed with former screen star Sarah Jessica Parker: he took the well-liked Silverstone and made her into a TV dream girl--with winning personality, great clothes and an enviable urban lifestyle--and plugged her into "Miss Match" (NBC, 2003- ), a lighthearted, romance-minded series in which she starred as Kate Fox, divorce lawyer by day and professional matchmaker by night. Although sweeter and not as edgy as "Sex," "Miss Match" successfully revived interest in Silverstone and rekindled her "Clueless" image as a cute, good-hearted, ideal gal pal--although more grown-up. However, the show struggled to find an audience. Meanwhile, the actress stayed active on the big screen as well with a turn as a sexy investigative reporter badgering Scooby, Shaggy and the gang in the sequel "Scoopy Doo 2: Monster Unleashed" (2004), and had a scene-stealing comedic dance sequence in the "Babershop" spinoff with a female slant, "Beauty Shop" (2005).