He entered the porn industry in 2004 at the age of 18. He has gained attention due to his relatively slender build, lack of tattoos and everyman appeal, bucking the stereotypical image of hypermasculine male actors in the pornography industry. In late 2015, multiple women came forward with allegations of sexual misconduct including nonconsensual sexual activity.
According to Deen, performing in pornographic films was his ambition since he was in kindergarten. After entering the pornography industry in 2004, he initially worked with older female performers. In 2009, he was named the "Male Performer of the Year" by AVN at the age of 22, making him the youngest actor to have won this award. Deen has a fan-following among teenage girls, a demographic that is typically not associated with the pornographic industry. In February 2012, ABC Nightline aired the feature Porn's Boy Next Door, which included interviews with both Deen and his fans. One fan described him as "the Ryan Gosling of porn".
In September 2012, Deen was a participant in a press conference, along with others opposing Los Angeles County Measure B, an initiative which would require condom usage in the pornographic film industry. Deen questioned the measure's constitutionality.
Deen's collaborations include work with NSFW site WoodRocket.com. As the host of original web series, James Deen Loves Food, Deen has been featured reviewing top restaurants, to ordering every item on a drive-thru menu at once, and creating a $580 burrito.
In January 2013, Deen took to crowdfunding site Kickstarter.com to raise funds for the mainstream steampunk Western film Cowboys & Engines. Deen is listed as the producer of the Bryn Pryor vehicle. The campaign surpassed its goal of $100,000 in 58 days. Actors Malcolm McDowell, Richard Hatch and Walter Koenig have signed on to the project.
In February 2013, Deen was invited to return to his alma mater, Pasadena City College, by professor Hugo Schwyzer to speak to students about his career. The appearance, initially open to the public, was restricted by college administrators due to "public safety concerns" over "protesters". Deen was restricted to speaking to the students of Pasadena City College's "Navigating Pornography" class.
Deen has been invited to college and university campuses across the country to speak with students on legislation, condom use and contraception, relationships, media, and sexuality. Deen also spoke to students at the University of Wisconsin – Madison on April 18, dubbed A Night with James Deen: Pornography & Sex Ed, as the keynote for the university's Sexual Health Fest.
Deen was featured in a July 2012 GQ multi-page article, chronicling his work and personal life. GQ interviewed Deen again for an article about his workout regimen, in which he credited healthy eating habits, a "Jew stomach" and lots of sex. In 2013, Deen was listed as the only male performer to make the CNBC Dirty Dozen list of the porn industry's popular stars.
In April 2013, Deen filmed a pornographic scene with reality television participant Farrah Abraham, who had been in one of the Teen Mom series. Deen indicated that he was asked to pretend to be dating Abraham as part of a ploy to market the scene as an accidentally released sex tape, but that he refused to do so, arguing, "If you're going to make a celebrity sex tape and try to pass it off as an amateur home video, you don't hire a well-known porn star!".
Deen co-starred with Lindsay Lohan in Paul Schrader's 2013 film The Canyons, written by Bret Easton Ellis. In July 2013, Deen teamed with American pornographic actress Andy San Dimas, adult app store MiKandi and adult industry news source XBIZ, to release the first adult video production recorded with Google Glass. Within 24 hours, the censored trailer reached 1 million views on YouTube.
Deen filmed a sex scene with Huffington Post blogger and comedian Jenn Tisdale in late 2013, in a New York City hotel room, after she responded to an open invitation by Deen on Twitter. Tisdale performed in the scene under the name Gwen Derringer and the scene was released on the 2014 adult DVD entitled James Deen's Sex Tapes: Hotel Sex. In November 2015, in light of sexual assault allegations made against Deen, Tisdale addressed the issue by amending her original story about filming a sex video with Deen, saying she regretted contributing to the false image Deen projected of himself.
Deen has a sizable fan base; his fans, dubbed "Deenagers", have created social media fan pages on Tumblr, Pinterest and standalone fan sites. Deenagers regularly share and comment on Deen's work. In February 2013, Deen launched JamesDeenStore.com.In addition to Deen's films and adult novelties, the store features Deen's Baby Panda brand of clothing.
In January 2014, Deen joined the newly formed Adult Performer Advocacy Committee team (APAC), which provides representation for performers within the adult film industry, protects performers' rights, reviews existing health and safety protocols, and initiates new ones as needed. As part of the Committee's launch, APAC released a Porn 101 video. A DVD copy was released to all industry talent attending the recent Adult Entertainment Expo in Las Vegas, Nevada. Deen has served as Treasurer and served as Chairperson of APAC until December 2015, when he stepped down following accusations from fellow performers.
In June 25, 2014, Deen participated in a Reddit A.M.A.. Deen received over four thousand questions over the course of an hour, making Deen's AMA listed by Reddit as the most popular on the site as of the following morning. Questions ranged from those about his career, personal life, condom legislation, the Teen Mom Farrah Abraham sex tape and more.