[19] Darrow read comics, mostly DC, from an early age, but he only decided to pursue a career in illustration after first seeing Jack Kirby's work in Fantastic Four Annual #3.

[21] Darrow sought out all available Blueberry volumes, gradually moving to other European works, such as Jean-Claude Mézières' Valérian and Greg and Hermann's Bernard Prince.

[19] In the late 1970s, he moved to Los Angeles and joined Hanna-Barbera, where he worked as a character designer on a number of cartoon series, including Super Friends in its various incarnations.

[20][23][25] In 1982, Darrow met French comic book creator and his artistic idol Mœbius, who was staying in Los Angeles while working on Tron for Disney.

[20][26] Upon learning that Darrow is an artist interested in creating comics, Mœbius arranged a meeting for him with Les Humanoïdes Associés, the publisher of French science fiction anthology Métal Hurlant, and offered to collaborate on some sort of project.

[22][21] Despite that, they were able to produce an art portfolio titled La Cité Feu, penciled by Darrow, inked and colored by Mœbius, published in 1984 by Éditions Ædena.

[20][32] Between 1990 and 1992, Dark Horse published the three-issue mini-series titled Hard Boiled, which earned Miller and Darrow the 1991 Eisner Award in the "Best Writer/Artist Team" category.

In 1994, Dark Horse started a new imprint titled Legend, spear-headed by Frank Miller and John Byrne and encompassing works by various creators including Art Adams, Mike Mignola and Darrow.

[34] After finishing Big Guy and Rusty, Darrow decided to return to his Bourbon Thret character but felt he needed to "adapt" him for the American audience.

[37]Meanwhile, relative unknowns the Wachowskis (having only directed the 1996 film Bound, as a low budget "audition piece"),[38] impressed by Darrow's art for Hard Boiled, wanted to work with him on their production for The Matrix.

[63][25] Since then, Dark Horse has re-released Hard Boiled and The Big Guy and Risty the Boy Robot with new coloring by Stewart as well as the entirety of Shaolin Cowboy in a uniform format.

[19] Outside of comics and film, Darrow has contributed artwork to a number of trading card series, including Magic: The Gathering,[66] Star Wars Galaxy,[67] Witchblade,[68] The Shadow and Madman,[17] as well as promotional posters,[69][70] CD covers and role-playing games.

),[73][25] Jean-Claude Mézières, Hermann,[22] François Boucq,[32] Osamu Tezuka, Katsuhiro Otomo,[53] Sanpei Shirato,[20][25] Vaughn Bode, Jack Davis, Richard Corben,[28] as well as the films of Anthony Mann[18][19] as his artistic influences.