For my money, one romantic comedy stands out as the best of all time, The Philadelphia Story, starring Cary Grant, Katherine Hepburn and Jimmy Stewart. First off, let me start by confessing my man crush for Cary Grant. While completely straight, I love everything about Cary Grant movies. He just was the perfect Hollywood actor from his unique accent, his mannerisms and his impeccable fashion style.
No surprise then that my favorite romantic comedy would prominently feature Grant. While Stewart might have had the higher billing in this film overall, it really is Cary Grant and Katherine Hepburn that make this story sing. Dex Haven (Grant) and Tracy Lord (Hepburn) are long time family friends that were briefly married several years ago. However, their fire and ice personalities quickly drove them apart. Now, thought Lord is set to remarry a wealthy businessman and Dex has shown up at the Lord family household on the weekend of the wedding.
Secretly, he has not ever gotten over Lord and wants to find a way to prevent the marriage from going forward. Meanwhile, much to his chagrin Macauley Conner (Stewart) must cover the wedding for his newspaper. He is a "real newsman" and feels the assignment is an insult to his news credentials. However, he is quickly smitten with Lord and becomes a pawn in Haven's scheme to stop the wedding.
This film is both funny and charming and will leave you feeling good about classic Hollywood. Haven's scheming is subtle, yet effective. Director George Cukor was brilliant and bringing out the tension between Haven and Lord as backdrop to why they broke up, but yet all the while leaving the audience feeling that they should end up together.
If you have never seen this wonderful film, I highly recommend that you put it at the top of your "must see" list as it truly is one of the best romantic comedies ever.