He is best known for his casting series where he specializes in having first-time female adult models perform rough anal sex and double penetration.

[6][7][8] Early in his career, Woodman would arrange meetings with women in hotel rooms under the guise of fashion modelling before revealing his intent of having them engage in sexual acts.

In 2004, after playing himself in the Spanish film Yo Puta, alongside Denise Richards and Daryl Hannah, he did several photo-shoots for fashion magazines, such as Vogue and Blast.

[11] With the breakup of the former Soviet Union in the early 1990s, Central and Eastern Europe became a new center of pornographic production, with actresses available for a fraction of the cost of American performers.

[9] While some actresses would initially refuse to perform the acts and voice their disappointment at being tricked, Woodman would spend an extensive amount of time convincing them to change their mind, often cutting this portion from the final movie or scene.

[13] In 2013, following the airing of a documentary on Woodman, the French online magazine Le Tag Parfait published an article that accused the director of pushing unsuspecting performers into engaging in unplanned sexual acts with him.

[6] In 2017, Lana Rhoades accused Woodman of coercing her into performing acts she did not want to do during a shoot and that he allegedly admitted to violating another woman's rights to her.