15. Say Anything… (1989)
Cameron Crowe’s directorial debut marked him out as a rising talent well worth keeping an eye on, as the young filmmaker made it abundantly clear he had his finger on the pulse of youth culture.
The story of high school romance is as timeless and overused as any plotline across any genre, btu John Cusack sells the whole thing with an earnest and charismatic charm that freshens up the tired formula to no end.
The iconic boombox scene alone is enough to burn Say Anything… into the public consciousness, but everyone involved is firing on all cylinders to craft a Gen-X classic that still holds up today.
