Hensley's parents moved to Los Angeles, where Hensley still lives, at the age of three. Hensley's father, was an avid comics reader, reading Marvel, DC, Warren magazines, underground comix, and Heavy Metal Magazine. In 1989 Hensley discovered alternative comics and a few years later started to focus on becoming a cartoonist. In 1989 Hensley mailed Daniel Clowes after noticing his mailing address in the back of an old Lloyd Llewellyn issue he was reading. Hensley asked Clowes if he would be interested in doing the cover art to an album he was working on for his band, Victor Banana. Clowes did the cover art and then asked Hensley if he would be interested in creating a soundtrack to one of the stories in his upcoming one-man anthology Eightball. The story was Like a Velvet Glove Cast in Iron. The album was released in 1993. Hensley's father, Tom Hensley, is a keyboardist and songwriter for Neil Diamond.
Publications
Ticket Stubminicomics — after college while working as a closed-captioning editor, Hensley would jot down the time code of any frames he found of interest in the video he was working on. After he had transcribed the video and if he had spare time, he'd create drawings based on these frames. Some of these drawings Hensley published as minicomics titled, Ticket Stub. The minicomics ran for 9 issues. In 2012, Yam Press published the collection as a book with the same title, Ticket Stub.
Wally Gropius — Wally Gropius is the main character in the book and resembles a teenaged Richie Rich or a classmate of Archie Andrews at Riverdale High. The book itself resembles a 1960s teenage humor comic but it is a satire. Hensley named the book after the famous architect, Walter Gropius, because he thought the name sounded humorous. In 2014 Tim Hodler, editor of The Comics Journal, wrote "Wally Gropius...is on a shortlist of essential graphic novels of this millennium."
Sir Alfred No. 3 — In Sir Alfred No. 3, Hensley turns the life of the famous film directorAlfred Hitchcock into 65 comic strips, most of which employ the look of Little Lulucomic books. Ken Parille of The Comics Journal calls the book an "oblique biography", where some of Hensley's strips play it straight while with others he chooses to expand, compress, or combine incidents which amplify the comedy and perversion of the director's life. Hensley ignores chronology, omits milestones in the subject's life, and even draws moments when young and old versions of the protagonist meet. Hensley hand-lettered the oversized comic. He collaborated with Alvin Buenaventura and the comic was published by Buenaventura's Pigeon Press. Buenaventura carefully oversaw every aspect of its manufacture and printing. One thousand copies were signed, numbered and included a giclée print of a scene from the filming of Psycho as well as a letterpress coaster. It was packaged in a custom-made Mylar sleeve. Issues #1 and #2 of Sir Alfred do not exist.