Smith is known for his portraiture in a style that blends influences including abstract painting and comic book art. These portraits include his series of paintings of strippers,
Girls in the Naked Girl Business, two of which are in the collections of the
Museum of Modern Art and the
Whitney Museum. Some of his works are shown on
Artsy. His work ''Pictures Showing What Happens on Each Page of
Thomas Pynchon's Novel
Gravity's Rainbow'' is a multimedia composition of 760 drawings, photos, and paintings, one for each page of the novel's first printing. It was exhibited at the 2004
Whitney Biennial and is now owned by the
Walker Art Center. Smith has written for
role-playing games such as
Lamentations of the Flame Princess,
Demon City, the
Cube World series of adventures,
I Am the Weapon, and
Places to Go, People to Be. Several of his contributions received awards, including multiple
ENNIEs for various
Lamentations of the Flame Princess products. Smith is also known as an
adult film actor. In February 2019, due to allegations of sexual abuse by several women including his former wife, adult industry performer Mandy Morbid,
Wizards of the Coast announced that they would be removing all references to Smith from the print and digital editions of
Dungeons & Dragons fifth edition,
OneBookShelf announced it would no longer work with Smith, and he was also banned from attending
Gen Con. Smith denied the accusations and filed defamation lawsuits against Morbid and other people. His defamation suit against Gen Con was dismissed in May 2023 after Smith deliberately violated
discovery rules by failing to respond to Gen Con's requests, a decision upheld by the
Washington Court of Appeals in October 2024. ==Personal life==