There's a reason Cusack is so good at playing bad guys — he actually enjoys getting into that headspace. "You want the characters to be better than you, so you can learn something from them," Cusack told GQ. "And if they're much worse than you, you can learn something, too."
From the war-profiteering assassin from "War, Inc." to the manipulative puppeteer from "Being John Malkovich," Cusack has starred in countless movies where viewers are likely rooting against the hero. He summed it up perfectly in an interview with The Guardian: "My characters often know it's wrong but do it anyway."
When The New York Times suggested that maybe Cusack's character from "High Fidelity" might embody a form of toxic masculinity, Cusack wholeheartedly agreed, saying, "If somebody was writing that Rob was a passive-aggressive womanizer, I'd be like, 'All right, somebody got it.'" He was hoping viewers would pick up on Rob's flaws and did not feel the need to sanitize Rob or make his character a more decent person; instead, he felt it was more important that he portrayed a realistic character than a likable one in the film.
Cusack also explained that when he plays antiheroes, he tries to understand how they see the world. For instance, he decided that Martin Blank, the assassin from "Grosse Pointe Blank," became a killer because he figured that was the only way to get ahead in his pursuit of the American Dream. "Like, a killer's a bad thing, right?" he told the Times. "But we could all be that person."