Best: Say Anything... (1989)
Fan favourite teen comedy, in which Cusack plays Lloyd Dobler (a role he beat Christian Slater to), a sharp, charismatic outsider. He makes eyes at Diane, an over-achieving lovely. They fall for each other, fall out, then attempt to work through their issues.
During that infamous boom box serenade scene, Cusack was playing his favourite Fishbone tape, not Peter Gabriel’s ‘In Your Eyes’ as in the final cut.
“I'm aware of the affection those characters inspired,” says Cusack. “I feel close to Lloyd in
. He was like a super-interesting version of me. Only I'm not as good as him. Whatever part of me is romantic and optimistic, I reached into that to play Lloyd. Of course, now it's all gone. Now I'm just bitter.”