Editing Heather Graham (section)

=== From ''Drugstore Cowboy'' to ''Swingers'' (1989–1996) ===
In 1989, Graham was featured in [[Gus Van Sant]]'s ''[[Drugstore Cowboy]]'' as Nadine, a young, drug-addicted accomplice of the two main characters (played by [[Matt Dillon]] and [[Kelly Lynch]]). Her performance gave her career an initial boost and earned her a nomination for the [[Independent Spirit Award for Best Supporting Actress]]. She rejected a steady role in a soap opera and a three-picture deal with a major studio because she thought it would be too restrictive.<ref>{{cite web|last=Lou|first=Linda|title=The more risks, the more rewards|url=http://159.54.226.237/99_issues/990808/990808graham.html|work=USA Weekend Magazine|access-date=December 2, 2012|archive-date=January 16, 2014|archive-url=https://web.archive.org/web/20140116131222/http://159.54.226.237/99_issues/990808/990808graham.html|url-status=dead}}</ref> After ''Drugstore Cowboy'', she appeared in [[Lawrence Kasdan]]'s dark comedy ''[[I Love You to Death]]'' (1990), alongside [[William Hurt]] and [[Keanu Reeves]], and the rock-and-roll coming-of-age film ''[[Shout (film)|Shout]]'' (1991), for which she received a nomination for the [[Young Artist Award]] for Best Actress Starring in a Motion Picture.

After Graham co-starred with [[Benicio del Toro]] in a [[Calvin Klein]] commercial directed by [[David Lynch]], the director cast her as Annie Blackburn in ''Twin Peaks'', where she appeared in the final six episodes. Following the show's cancellation, Graham reprised the role of Blackburn in the 1992 prequel film ''[[Twin Peaks: Fire Walk with Me]]''.<ref name="grouchoreviews.com"/>

She featured in ''[[Diggstown]]'' (1992), alongside [[James Woods]]; the well-received ''[[Six Degrees of Separation (film)|Six Degrees of Separation]]'' (1993), alongside [[Will Smith]]; and ''[[The Ballad of Little Jo]]'' (1993), alongside [[Ian McKellen]] before reteaming with Gus Van Sant for the critically panned [[Even Cowgirls Get the Blues (film)|film adaptation]] of ''[[Even Cowgirls Get the Blues (novel)|Even Cowgirls Get the Blues]]'', alongside [[Uma Thurman]].<ref>{{cite web|title=Even Cowgirls Get the Blues (1994)|url=https://www.rottentomatoes.com/m/even_cowgirls_get_the_blues/|website=Rotten Tomatoes|access-date=December 2, 2012|archive-date=November 27, 2012|archive-url=https://web.archive.org/web/20121127182714/http://www.rottentomatoes.com/m/even_cowgirls_get_the_blues/|url-status=live}}</ref> The same year she co-starred as Mary Kennedy Taylor in ''[[Mrs. Parker and the Vicious Circle]]''. In 1995, she starred as Jackie in the poorly received ''Desert Winds'' and guest-starred in an episode of the television series ''[[Fallen Angels (American TV series)|Fallen Angels]]''. She had a small but important role in ''[[Swingers (1996 film)|Swingers]]'' (1996), where she played Lorraine, [[Jon Favreau]]'s love interest.<ref>{{Cite magazine|date=2016-10-18|title=This Interview About the Anniversary of Swingers Is So Money|url=https://www.vanityfair.com/hollywood/2016/10/swingers-20th-anniversary-interview|access-date=2022-01-13|magazine=Vanity Fair|language=en-US|archive-date=January 22, 2022|archive-url=https://web.archive.org/web/20220122045504/https://www.vanityfair.com/hollywood/2016/10/swingers-20th-anniversary-interview|url-status=live}}</ref> She also played a small role as Maggie Bowen in ''[[Entertaining Angels: The Dorothy Day Story]]'' (1996).