I believe the joke is that Anthony Michael Hall is known for being a lovable nerd hero in 80s movies, but in his middle age, he looks a bit like Malcolm McDowell, who is known for playing the baddie in A Clockwork Orange and also in Star Trek: Generations. So… hero to villain, like the very common expression.
I believe the joke is that Anthony Michael Hall is known for being a lovable nerd hero in 80s movies, but in his middle age, he looks a bit like Malcolm McDowell, who is known for playing the baddie in A Clockwork Orange and also in Star Trek: Generations. So… hero to villain, like the very common expression.