Her journey into XXX started with a boyfriend who introduced her to bondage, anal sex, and rough sex. She loved every hardcore minute of it, encouraging him to try things that were more hardcore than he thought she would enjoy. This is also when she discovered her love of porn. Sasha and her boyfriend would watch porn as a couple and then try to emulate it in real life. Grey said that one day it just clicked that porn is what she was going to do with her life. Sasha knew that porn would be a stepping-stone for her to get into mainstream productions. Clearly she was right.
Sasha Grey started filming porn just months after she turned 18. Mark Stiegler was an agent that was casting a film by legendary XXX icon John Stagliano: "Fashionista Safado: The Challenge". A girl who was previously cast needed to be replaced, so Sasha Grey replaced her and got her big break. The film was one of the most watched films that year. Her performance was so remarkable that, despite being in the film with top pornstars, she captivated fans and became a XXX household name almost overnight.
Sasha Grey has performed in over 300 adult films and even got into the director’s chair for a few of them. In 2008, Sasha’s prediction came true and she started her mainstream crossover. Sasha landed a role in the Superchrist music video by The Smashing Pumpkins, as well as in the video for the song Birthday Girl by The Roots. In 2010, she got her big mainstream break by landing a starring role in The Girlfriend Experience. The movie was about escorts and was perfect to show off her mainstream acting skills while blurring the lines between porn and Hollywood. Her hybrid career came full circle when she landed her role in HBO’s Entourage playing herself, and the rest is history!