[5] She graduated a year early at the age of 17,[16] and in late 2005, she attended Sacramento City College and took classes in film, dance, and acting.

[2][18][19] She initially considered calling herself Anna Karina,[5] after the French New Wave actress of the same name, before choosing Sasha Grey.

[22][23] Less than six months after entering the adult industry, Grey was featured in the November 2006 edition of Los Angeles magazine where she was flagged as a potential major star, perhaps the next Jenna Jameson.

[25][26] In 2008, she became the youngest woman ever to win the AVN Female Performer of the Year Award[27] In 2008 Grey announced that she would represent herself in the adult industry through her agency L.A.

[31][32][33] A. O. Scott of The New York Times described Grey's pornography career as "distinguished both by the extremity of what she is willing to do and an unusual degree of intellectual seriousness about doing it".

[52] She has modeled for artists James Jean,[53] Zak Smith,[54] Dave Naz,[55] David Choe,[56] and Frédéric Poincelet,[57] who also created the artwork for her industrial music band aTelecine's ...And Six Dark Hours Pass album.

[62][63] Richard Phillips made a short film called Sasha Grey in the Chemosphere for the Gagosian Gallery in 2011 and also portrayed her for the Frieze Art Fair in 2013.

[5][70] As Grey prepared for her role in The Girlfriend Experience, Soderbergh asked her to watch Jean-Luc Godard's films Vivre sa vie and Pierrot le Fou, both of which star Anna Karina.

[79] In 2016, Glenn Kenny who played the majordomo of an escort-review site, described The Girlfriend Experience as a "digital film from another era", with most scenes being two-handers.

[80] Grey appeared in a 2009 episode of James Gunn's PG Porn with James Gunn,[81] made a cameo appearance in Dick Rude's 2010 independent film Quit,[18] and starred in the 2009 Canadian low-budget black comedy/horror film Smash Cut with David Hess from Odessa/Zed Filmworks.

[82] Grey played a fictionalized version of herself in the seventh season of the HBO series Entourage as Vincent Chase's new girlfriend in a multi-episode arc.

[79] Grey played Raven in the thriller I Melt With You, directed by Mark Pellington, which premiered at the Sundance Film Festival on January 26, 2011.

[85] She co-starred in the 2012 horror-thriller Would You Rather, which was directed by David Guy Levy, and which has a critics' consensus rating of 59% based on 22 reviews at Rotten Tomatoes.

[79] A critic noted the similarity of her role as "unflinching in the wildest of circumstances, when vying for a hefty sum of cash at the expense of [her] health" to Grey's own career as an adult actor.

[96] In 2008, Grey began an industrial music collaboration called aTelecine with Pablo St. Francis[12] and the two later added Anthony D' Juan and Ian Cinnamon.

[98] Paul Maher Jr. compared Sasha Grey with Cathy Ames in John Steinbeck's novel East of Eden, describing the ambient tracks of aTelecine as aural wrecking balls, stated that Grey's artistic temperament comes close to that of the Marquis de Sade as "a proponent of freedom tethered to its furthest extremities, yet untethered by laws, morality or religion" and admired her courage and audaciousness.

[104] The former Throbbing Gristle members Chris & Cosey remixed "Consequences of Love", a Transmission song performed and composed by Grey and Fearless.

[107] In a cameo appearance, DJ Harvey plays "Consequences of Love" in the rave party at the Grand Palais scene of Mission: Impossible – Fallout.

[108] In 2018, Death in Vegas published the single "Honey", with Grey as writer, singer, and film director of Drone Records' video for the song.

[116][117] BlackBook described it as "another right step in transforming herself into the multimedia artist she sees herself as"[118] and the Portland Mercury compared Grey's "distinct style" with the photography of Cindy Sherman and Terry Richardson.

[120][121] Karley Sciortino described the book as a "satirical, erotic novel that follows Catherine, a film student who enters a secret, elite sex society", and in an interview Grey stated she paid homage to novels like The 120 Days of Sodom, Thérèse the Philosopher, and Voltaire's Candide.

[122] Alisande Fitzsimons wrote that The Juliette Society contains references to classic erotic literature and film,[123] and Cosmopolitan UK called it "erotica with a difference".

After some parents complained, Grey responded to the controversy by stating, "I committed to this program with the understanding that people would have their own opinions about what I have done, who I am, and what I represent".