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Bolland began drawing comics at the age of ten. As a child, his main inspirations were titles by Dell Comics and DC.

While at art school, Bolland drew and self-published a couple of fanzines and had work published in British underground magazines Friendz, International Times, OZ and Time Out. In 1972, at the Comic Convention held in the Waverley Hotel in London, he met Dave Gibbons. On Gibbons' recommendation Bolland joined art agency Bardon Press Features and it was Bardon who provided Bolland's first professional work: Powerman, an African superhero comic published in Nigeria. Bolland and Gibbons drew alternate issues. In 1977 Bardon found places for Gibbons and then Bolland in the new British science fiction weekly 2000 AD. Bolland's first work was a cover on issue ("Programme") 11. Other covers followed, stand-alone pages and some inking of Gibbons' Dan Dare. When another artist dropped out, Bolland was called in to complete a Judge Dredd story in issue 41 and soon was established as a regular artist on the series. Bolland's early work on Dredd was much influenced by Mike McMahon a talented newcomer whose idiosyncratic style was fueling the interest in the new character. However, Bolland's distinct abilities with subtle facial expression, dramatic lighting and the dynamic composition of page layout soon began to emerge. Bolland's memorable contributions included the introductions of Judge Death and Judge Anderson. In between Dredd assignments Bolland drew horror strips for the House of Hammer, the occasional record cover, covers for paperbacks and magazines (including the now-established Time Out) and work in the advertising industry.

Bolland began working for DC Comics in 1979 with covers and short stories. In 1982, DC editor Len Wein chose Bolland as the artist on DC's Camelot 3000 12-issue limited series, with writer Mike Barr (dealing with the return of King Arthur to save England from an alien invasion in the Year 3000). In 1988 Bolland produced the art for the Batman graphic novel Batman: The Killing Joke, written by Alan Moore.

However, Bolland is recognized more as a cover artist; he has contributed covers — in many cases to complete runs/arcs — to some of the more famous landmark comics of recent years. Examples of his work include the whole second and third volumes of Grant Morrison's The Invisibles, a large run of Animal Man (covering the tenures of Morrison, Peter Milligan, Tom Veitch and Jamie Delano), and assorted issues of Tank Girl, The Flash, Superman, Green Lantern, Wonder Woman, Batman (esp. Batman: Gotham Knights), and many more.

He is also noted for his use of bondage imagery in some of his work. Additionally, Bolland has penned the humour strip Mr. Mamoulian, which was printed in various issues of the Caliber Comics anthology Negative Burn. Also his occasional strip The Actress and the Bishop, all of which were collected in the book Bolland Strips! in 2005.

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