Olson entered the pornographic film industry in November 2006, and initially worked for a variety of companies including Digital Playground, Elegant Angel and Red Light District Video. She was a contract performer with Adam & Eve from 2007 to 2010. She has performed in over 280 pornographic movies.
In 2007, Olson appeared in an episode of the first season of E! reality show Keeping Up with the Kardashians, in which she is hired as a nanny but ostensibly gets fired on her first day at work after then-matriarch Kris Jenner objects to her state of dress and behavior as "inappropriate." In reality, the show's producers attempted to "milk a 'slutty babysitter' stereotype for laughs."
Olson was named Penthouse Pet of the Month for March 2008, appeared on the cover of Hustler, was on the cover of the May 2011 issue of Penthouse, and on the cover of the August 2011 Playboy magazine. In 2010, she was named by Maxim as one of the 12 top female stars in porn. In October 2011, Olson announced that she had retired from shooting pornography, and that "she hasn't done an adult film in over a year."
Olson was born in Houston, Texas. Olson's maternal grandparents were Ukrainians who immigrated to Texas, then Fort Wayne, Indiana, when she was two years old. On March 1, 2011, Olson was reported to be living with actor Charlie Sheen. The relationship ended in April 2011.
In 2013, Olson was confirmed as a member of the cast of the horror film The Human Centipede 3 (Final Sequence) and Penn Jillette and Adam Rifkin's Director's Cut. In 2015, she played Divatox in the short, web film Power/Rangers.
On June 17, 2015, Olson posted an open letter on Twitter advising women to avoid the adult film industry. On March 24, 2016, writing as a guest columnist in Daily Dot, she related her post-porn social life, stating, "porn didn't hurt me. The way society treats me for having done it does". In the same article, she claimed she is "broke", although independent sources had claimed in 2015 she was "worth US$ 5 million. This article was later followed by her March 25 appearance in the YouTube documentary series "Real Women, Real Stories", in which she repeated these claims, adding that she believes society in general perceives ex-porn stars in a highly negative manner, specifically as morally akin to pedophiles. She is also critical of the pornography industry, noting "We are the only entertainment industry that doesn't offer talent royalties after they are gone," but not of the profession itself.