Moebius introduced Darrow to Frank Miller which led to a friendship and eventually two collaborations. In 1990, Darrow and Miller collaborated on the comic book Hard Boiled, a 3-part mini-series, for which they won the 1991 Eisner Award for Best Writer/Artist.
Darrow and Miller worked together again on Big Guy and Rusty the Boy Robot in 1996, a far more family-oriented work, in which the protagonists save Tokyo from destruction by a giant lizard. The story was later developed into a 26-episode animated series of the same name, produced by Columbia TriStar Television and Dark Horse Entertainment, which aired from 1999 to 2001.
The Wachowskis saw his work on Hard Boiled, and approached Darrow to do some conceptual work for The Matrix. Darrow was credited as 'Conceptual Designer' on all three Matrix movies.
His visual style is most prominent in the scene of Neo's awakening from his biomechanical sleep. The insect-like machine that attacks Neo is a classic Darrow mechanoid made up of tubes, viewscreens and riveted joints. He has also contributed to both volumes of The Matrix comics, a series of short Matrix-inspired comic stories.