Rise to Fame
A traveling coffee salesman. That was his career until a girlfriend dragged him to an acting class, a detour that led to Lindsay Anderson's If.... (1968) and then to Stanley Kubrick rewatching the punishment scene four times to decide he'd found his Alex DeLarge. A Clockwork Orange turned him into a counterculture emblem overnight. He spent the first ten years after it resenting the film, then eventually concluded it was a masterwork, and he was very much part of it.
In the Spotlight
After A Clockwork Orange, he spent decades running from Alex DeLarge's shadow. He took the role in Star Trek: Generations (1994) when they asked how he'd like to kill Captain Kirk, which seemed fun until the death threats from Trekkies arrived. He got his Hollywood Walk of Fame star in 2012, became an American citizen in 2021, and is now playing a warm-hearted grandfather in the Canadian series Son of a Critch. Nobody who watched A Clockwork Orange would have predicted Pop Critch.
Side Notes
His real name is Malcolm John Taylor, changed to his mother's maiden name because another actor had already registered Malcolm Taylor with Equity. On set for A Clockwork Orange, the eye clamps in the Ludovico scene scratched his cornea and left him temporarily blind. In 2012, that injury reportedly contributed to a detached retina requiring emergency surgery. Stanley Kubrick also brought a live snake to set knowing McDowell was terrified of reptiles. Direction or cruelty, the line was always thin.