Ranking The 25 Best Rom-Coms of All-Time

22. How to Lose a Guy in 10 Days (2003)

Image Source: Bustle

Alright, Alright, Alright. Only a true rom-com would have leads named Andie Anderson and Benjamin Barry. It’s a film that centers on a cool girl, whose chemistry with a chauvinistic man’s man is undeniable. Andie (Kate Hudson) works for a women’s magazine that is “growing”; Benjamin (Matthew McConaughey) is wearing shirts, and “Knicks” tickets were of great value. Andie wants to write about subjects with substance — which, for the moment, requires her to ensnare a man and torture him to the point of breaking up. He, meanwhile, is simply trying to win a big campaign at work by proving he can make any woman fall in love with him. They fall in love, and its basically impossible to do anything but cheer them on in the process.