2. There’s Something About Mary (1998)

Best comedies of the '90s - Cameron Diaz in There's Something About Mary

Something of a dark horse to grace the number two spot perhaps, but this Farrelly Brothers comedy has it all. There’s Something About Mary stars Ben Stiller as Ted, a 30-something magazine writer still in love with his high school crush. Finally deciding to pursue her, he learns that he’s just one of a number of people infatuated with Mary (Cameron Diaz), throwing a wrench in Ted’s romantic plans.

There’s Something About Mary did more than just cement Ben Stiller as a leading man. Cameron Diaz further secured her status as an A-list talent, not just for her looks but her comedic abilities. A supporting cast of Matt Dillon, Chris Elliott, Lee Evans, Jeffrey Tambor, Lin Shaye, and Keith David secure There’s Something About Mary as one of the best (and funniest) romantic comedies of the ’90s.

In fact, There’s Something About Mary is so good that one or two moments from the film have entered the cultural lexicon. The shot of Diaz with her hair stuck upright with… organic hair gel will undoubtedly live forever, but there’s something to enjoy in every single scene. It seems there really is something about Mary, because it’s an outstanding comedy.