She made her film debut in the thriller The Crush (1993), earning the 1994 MTV Movie Award for Best Breakthrough Performance, and gained further prominence as a teen idol when she appeared in the music videos for Aerosmith's songs "Cryin'", "Amazing" and "Crazy".

[9] Her first credited acting role was on The Wonder Years in 1992, in the episode "Road Test", as Kevin's high school "dream girl".

[12] After seeing Silverstone in the three videos, filmmaker Amy Heckerling decided to cast her in the coming-of-age comedy Clueless, in the role of Cher Horowitz, a sweet but spoiled girl living in Beverly Hills.

The film only grossed $14.5 million in North America,[23] and received mediocre reviews from critics; Roger Ebert mentioned that she was "no better than OK" as he felt that she was miscast.

[24] Silverstone starred as the female lead in the romantic comedy Blast from the Past (1999), directed by Hugh Wilson and co-starring Brendan Fraser, Christopher Walken and Sissy Spacek.

[30] Silverstone executive produced and provided the voice of Sharon Spitz, the lead part, in the Canadian animated television series Braceface, from 2001 to 2003.

During this period, she played the bassist of a rock band in the independent comedy Global Heresy (2002), opposite Peter O'Toole and Joan Plowright, and made her Broadway debut alongside Kathleen Turner and Jason Biggs in a stage version of The Graduate, which ran between 2002 and 2003 at the Plymouth Theatre.

[citation needed] Silverstone signed on to headline the 2003 NBC television series Miss Match, as Kate Fox, a Los Angeles matrimonial attorney who doubles as a high-end matchmaker.

In 2004, Silverstone played a news reporter turned villainess in Scooby-Doo 2: Monsters Unleashed, opposite Sarah Michelle Gellar and Freddie Prinze Jr.[3] Despite a negative critical response, the film grossed $181 million at the international box office.

[32] In the comedy Beauty Shop (2005), a spinoff of the Barbershop film franchise, Silverstone appeared with Queen Latifah, playing a naive and bubbly stylist of an Atlanta-area salon.

Silverstone portrayed the close friend of a teenager turned secret agent in the action-spy film Stormbreaker (2006), directed by Geoffrey Sax and co-starring Alex Pettyfer, Ewan McGregor and Mickey Rourke.

[39] She obtained the role of a single mother returning to her hometown after a lengthy absence in the made-for-Hallmark Hall of Fame television film Candles on Bay Street, based on the book by Cathie Pelletier.

[40] The production was presented at the Geffen Playhouse theater in Los Angeles, with Variety writing that Silverstone "steals the show [in her role].

[42] In 2008, Silverstone filmed another unaired ABC pilot alongside Megan Mullally called Bad Mother's Handbook and made a cameo appearance in the action-comedy Tropic Thunder.

[3] In 2009, she starred in the music video for Rob Thomas's single "Her Diamonds",[43] and acted in Donald Margulies' production of Time Stands Still, set in Brooklyn and revolving around the relationships of two couples.

[52] Silverstone obtained the role of the teacher of a Manhattan private-school senior in the teen romance drama The Art of Getting By (2011),[53] which premiered at the Sundance Film Festival.

[55] She reunited with Clueless director Amy Heckerling in the independent film Vamps (2012), playing one of two vampires who fall in love and face a choice that could jeopardize their immortality.

[59] Silverstone guest-starred in Childrens Hospital (2011) and obtained a four-episode role in the first season of Suburgatory (2012), reuniting with her Clueless castmate Jeremy Sisto.

[62] The play premiered in November at the Longacre Theatre, but was canceled after 23 previews and seven regular performances due to the aftermath of Hurricane Sandy.

[63] In 2013, she filmed the television pilot HR,[64] which was not picked up,[65] and appeared in the Sundance comedy Ass Backwards, released for VOD and selected theaters.

[68] In 2015, Silverstone starred in the New York production of Of Good Stock, a play revolving around a group of siblings who gather at their family home for a summer weekend.

[69] Entertainment Weekly remarked that she was "magnetic even as an engaged narcissist, ditzy" sister;[70] however, The New York Times felt that her role was "the most cartoonish of the characters and a thankless part for [Silverstone], who tips into comic shrillness here".

[75] Silverstone starred in three 2017 films—Diary of a Wimpy Kid: The Long Haul,[76] The Killing of a Sacred Deer,[77] and The Tribes of Palos Verdes[78]—and filmed the television series American Woman in July of that year.

Yorgos [the Sacred Dee director] helped us to push my date and Diary of a Wimpy Kid held the movie for a week or two for me".

[81] In the psychological thriller The Killing of a Sacred Deer, directed by Yorgos Lanthimos and co-starring Colin Farrell and Nicole Kidman, Silverstone took on the role of a widow and the mother of a mysterious boy who befriends his late father's cardiac surgeon.

[84] Silverstone appeared in the comedy Book Club (2018),[85] opposite Diane Keaton, Jane Fonda and Candice Bergen, playing the "domineering" daughter of a "skittish" widow reading Fifty Shades of Grey.

In 2020, Silverstone appeared in the comedies Bad Therapy, Sister of the Groom[92] and Valley Girl, and also narrated the eco-superhero fantasy novel Chendell: A Natural Warrior[93] and the Audible podcast Eat S-t Kenny Daniels.

"[101] She has been criticized due to her anti-vaccine stance, promotion of pseudoscientific diet and lifestyle choices, and her claims regarding the medical and spiritual benefits of veganism.

[103] In 2007, she appeared nude in a print advertisement and 30-second commercial for PETA championing vegetarianism; the TV spot was subsequently pulled from the Houston, Texas market by Comcast Cable.