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Best romantic comedies bracket: Why we chose these 64 movies

Sally and Harry ("When Harry Met Sally")
Sally and Harry ("When Harry Met Sally") (MGM)

Welcome to our first bracket challenge of 2020 – the best Romantic Comedies of all time!

YES – the Rom-Com! What else is there to do during this cold and miserable January other than to argue best Rom-Com of all time!?!

Think of it as a March Madness bracket for romantic movie buffs. It’s 64 of the best romantic comedies ever made. And just like the basketball brackets, we picked four No. 1 seeds with each “region” hosting 16 movies.

Of course you might be wondering how we came up with all of this?? Well, after extensive research of every single Rom-Com list ever published online, plus exhaustive viewing (sometimes over and over and over) of many of these movies and, of course, endless conversations in the newsroom ... we landed here.

And since I have personally watched several of these movies dozens and dozens of times and consider myself (just as Joan Wilder did in Romancing the Stone) a “hopeful romantic," I decided to tackle the seedings and take the heat!

So how did we get here??

The top seeds are “When Harry Met Sally,” “Sleepless in Seattle,” "You’ve Got Mail’ and “Pretty Woman.” Why? Well “When Harry Met Sally” was really the movie that started the whole “Rom-Com” phenomenon right?! Plus, Meg Ryan and the deli scene alone make it a top seed.

“Sleepless in Seattle” gets a No.1 seed for several reasons -- mostly the performances by Meg Ryan, Nora Ephron and Tom Hanks. The film, which pays homage to “An Affair to Remember” (one of our No. 2 seeds by the way) is all about second chances and true love. Who doesn’t love that!?

“You’ve Got Mail” is our third No. 1 seed. The flick features the trio of Meg Ryan, Tom Hanks and Nora Ephron again. While it isn’t as good as “Sleepless in Seattle” (IMO), it does give us excellent banter between Meg Ryan’s character and Tom Hanks’ character, which is something we never really got in Sleepless.

I really wrestled with our final No. 1 seed. Originally, I was going to go with “It Happened One Night,” which starred Claudette Colbert and Clark Gable and is considered to be one of the very first romantic comedies. But since the movie came out in 1937, I was afraid too many people wouldn’t know it.

On the other hand, almost everyone I asked mentioned “Pretty Woman” as one of their favorite rom-coms. Since you can’t go wrong with Julia Roberts and Richard Gere and that necklace scene, it landed as the final No. 1 seed. Plus, not picking it would be a big mistake. Big. Huge.

On a side note: Since Meg Ryan is in three of the top four that must make her the Queen of Rom-Coms right!?!? Maybe that is a bracket for another time. 😊

As for the rest of the bracket, we tried to pick rom-coms from all across the board. We have movies from every decade starting in 1937 (“It Happened One Night”) and going all the way to “Crazy Rich Asians,” which premiered in 2018.

A couple of John Hughes films made the bracket after heated discussions about them being “coming of age” films instead. But you just can’t argue with the romance in “Sixteen Candles” and “Pretty in Pink,” so they made the list!

“The 40-year-old Virgin” is a an unorthodox romantic comedy, but after many of the men in the newsroom voted for it, I begrudgingly added it to our list.

As for the actors, while Meg Ryan is arguably the Queen of Rom-Coms, FIVE Hugh Grant films made our list. I guess that makes him the King of Rom-Coms?!?! Sorry, Tom Hanks.

Tom Hanks actually appears three times along with Meg Ryan, Julia Roberts, John Cusack (a bit of a surprise, too) and Cary Grant, of course.

Sandra Bullock and Jack Nicholson make it twice.

So that is a little of the behind-the-scenes of the making of the Rom-Com Bracket.

Of course, our main goal of all of this is to have a little fun! Let us know how you feel about our seeds and what movies you think we may have missed!

Most importantly, make sure to VOTE! -- you can do that here: