40. High Fidelity (2000)
Stephen Frears’ High Fidelity is hardly complicated or profound, but it certainly struck a chord with the intended audiences, and the soundtrack is never going to go out of fashion.
John Cusack stars as the owner of a rundown record store jilted by his girlfriend, leading him to look inward. With a little help from his friends, he ends up finally embracing change and growing up.
Cusack might be the lead, but the supporting cast are every bit as good, with Jack Black giving the breakout performance that took his career to the next level in an unconventional rom-com that still hits all the right notes.