38. She’s Gotta Have It (1986)
Spike Lee isn’t the first name that comes to mind when you think of romantic comedy, and She’s Gotta Have It is hardly conventional, but his first feature film definitely ticks many of the boxes required.
Nola Darling can’t decide who she wants to date, so she decides to test the waters with three wildly different guys at the same time, leading to plenty of internal and external conflict as a result.
She’s Gotta Have It displays many of the social and political angles that would go on to define Lee’s career, and it offers a standard Hollywood rom-com wrapped up in the singular talents of a soon-to-be hugely prescient and frequently incendiary filmmaker.