19. Diary of a Mad Black Woman
Lots of similar articles and lists choose Closer as a great breakup movie, and while there's something about its darkness that does help during a hard time, I think Diary of a Mad Black Woman is much more relevant.
Not every breakup is funny.
Breakups can be dirty, gritty, dark, and harmful to one or both parties involved.
If you need inspiration, if you need to see someone with strength and resilience, watch this one.