Woodman began working at 16, taking such jobs as bartender, salesman and store clerk. He joined the army at age 17, and later became a policeman. In 1986, he started a career as a fashion and TV photographer. In 1989, he took part in launching the magazine Hot Video, as a reporter. Beginning in 1992, he worked for the Private Media Group, Inc., for which he made several big budget movies, such as The Pyramid (1.2 million USD), Tatiana (600,000 USD), Riviera (450,000 USD).

In 1997, he launched his series "Casting X" (see below), which is now the biggest selling series in the X-rated category in the world.

In 1999, faced with a wave of "Gonzo" genre videos, Woodman began to produce and release his Superfuckers series for Private, which ran to 12 Chapters. Woodman showcased women, glamor, sex, excitement, passion and fun. At the end of the year, he received an invitation from Larry Flynt, owner of LFP, Inc. and a millionaire publisher of the magazine Hustler, the second largest magazine periodical in the US after Playboy. Hustler was on the verge of bankruptcy and Flynt knew he needed a video department to survive. He asked Woodman to create a series similar to Private and in 2000, Flynt signed a contract with Woodman for 5 million USD for five years. Woodman began Chapter 13 of Superfuckers for LFP. But unlike Berth Milton, Jr., owner of Private, Flynt spent little on advertising, relying instead solely on the Hustler name and word of mouth to sell products. This bothered Woodman, who made a few big budget movies, such as Brazilian Snake (2001) (520,000 USD), Brazilian Snake 2 (2002) and Manipulation (2004) (430,000 USD), but ultimately disappointed by the lack of promotion of the products, Woodman refused to sign a new contract for LFP in 2005.

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

Woodman then launched a program affiliation on the Internet called "Spider-Cash," to distribute its films in the form of video sequences, after Berth Milton, head of Private, asked Woodman to return to work for him in 2005.

Woodman made a trilogy Sex City, a "porn-remake" that "borrows" much of the storyline of Frank Miller's Sin City, including the clever use of black and white photography, with splashes of color inserted throughout the film. Woodman's Sex City was filmed entirely in high definition, with a budget of 540,000 Euros. The first part was released in May 2006. After five weeks, the film became the best selling in the history of Private, even taking the lead in sales in the U.S. on June 5, 2006.