It's weird you posted this now because I'm reading "You couldn't ignore me if you tried", a book about the 80's teen/brat pack movies, mostly John Hughes but Say Anything is in it too. I'm exactly at this point where Say Anything is talked about. It's such a different vibe, and I think more intelligent, than the Hughes ones. That's not a criticism so much as I believe Cameron comes at it in a different way. Crowe and James L Brooks didn't think the studio marketed it the right way, they thought it could be an Academy movie but the studio saw it merely as a teen flick. Cusack didn't want to do it as he'd already done The Sure Thing (Very underrated!) and Weird Science, but John Mahoney was already on board, and during filming Eight Men Out he convinced him to do it. Told him it's different.
In Crowe's book he shares the anecdote that he and Hughes had offices in the same bungalow on Paramount's lot but never really had a relationship. They'd see each ohter often. One night they stayed after and spent the night in the office together talking about movies and music. Then that was it. He never talked to him again. Wasn't sure why. Hughes was heavy into the British pop in the mid 80s and played a large part in making it popular here.