The Con Air star reveals he met with late tech guru Steve Jobs shortly after his hit film High Fidelity came out - and the Apple boss wowed him with his vision for the future of music.
But Cusack was too naive to jump at the chance to become an early investor.
He recalls, "He (Jobs) called me up and wanted to know if I would do a commercial for what was then gonna be iTunes and he took me through the iPad and iTunes and he showed me the whole thing; he basically showed me the future of music.
"I never actually thought that I should have bought Apple stock. That's how much I don't think about money. He literally laid it all out for me."
Cusack turned down the chance to become the face of Jobs' vision too, adding, "I didn't feel like doing a commercial."