After sighting the young Sevigny on the streets of New York, where she repeatedly drew notice for her distinct, idiosyncratic fashion sense, the yuppie author was moved to dedicate a seven-page New Yorker spread to her, in the course of which he anointed her with said title. Whether or not she was "It," Sevigny did enjoy a rudimentary helping of fame: at the time, she was an intern at Sassy magazine, where she had been employed after magazine writers spotted her and used her as a model for their publication.

Born in the wealthy, conservative suburb of Darien, Connecticut in 1975, Sevigny began hanging out in New York as a teenager. After her initial recognition from Sassy and McInerney, she made her screen debut in Larry Clark's Kids. Sevigny played one of the few sympathetic characters in the controversial 1995 film, a teen infected with AIDS by the so-called "virgin surgeon" to whom she had lost her virginity. The following year, she appeared as a bored Long Island teen in Steve Buscemi's directorial debut, Trees Lounge, and then went on to collaborate with Kids screenwriter and then-boyfriend Harmony Korine on Gummo (1997). Her pairing with the iconoclastic Korine led one magazine to dub them as the new John Cassavetes and Gena Rowlands, but the film was savaged by some critics and virtually ignored by its intended arthouse audience.

More substantial luck greeted Sevigny in her 1998 role in Whit Stillman's The Last Days of Disco; the film won a number of positive reviews, with praise for Sevigny's portrayal of a thoughtful Hampshire graduate trying to make it in the publishing world. The actress' other film that year, the little-seen Palmetto, cast her as a millionaire's stepdaughter. Sevigny was back the following year in A Map of the World, which premiered at the Toronto Film Festival; Boys Don't Cry, in which she played the girlfriend of Brandon Teena, a real-life girl who passed as a boy; and Julien Donkey-Boy, her third collaboration with screenwriter-turned-director Korine. Sevigny's role in Boys Don't Cry courted particular notice and critical praise, earning Sevigny Best Supporting Actress Golden Globe and Oscar nominations. Further notice greeted her part in American Psycho, Mary Harron's incredibly controversial 2000 adaptation of Bret Easton Ellis' novel of the same name.

Continuing to appear in such features as Demonlover and Party Monster in 2003, Sevigny once again found herself involved in a controversial film with her role in Vincent Gallo's The Brown Bunny. Premiering to much critical derision at the 2003 Cannes Film Festival (film critic Roger Ebert was quoted as saying it may be the worst film in the history of the festival), Sevigny shocked audiences by performing fellatio on the director/star in the film's explicit coda.