16. Clueless (1995)
A recurring theme throughout this list is that classic literary stories being reinvented and updated as modern day rom-coms has always been a recipe for success, and few did it better than Clueless.
The high school spin on Jane Austen’s Emma still boasts an incredibly loyal and dedicated fanbase to this day, as new generations continue to fall in love with the endlessly quotable and razor-sharp dialogue, brought to life by a cast all on top form.
Clueless went on to launch an entire multimedia empire that included a spinoff show, a stage adaptation, a novel series and comic books, but the feature film is still the only thing that matters.