Top 10 Romantic Comedies: Take Two

- Posted by Rusty

I know this looks like I’m stealing Luke’s thunder from last Thursday, but, from the outset, we wanted to do two separate lists on our Top 10 Romantic Comedies (since we’re dudes who love rom-coms way too much), and then see how they stack up (check out Luke's list here). Before I start, I should mention that these are more my favorite romantic comedies, as opposed to a list of the "best" in the genre - some are genuine classics, some I just love despite all their flaws, but all of these are ones I rewatch from year to year. Feel free to offer up your own choices for the ones Luke and I might have passed by, and let us know how our picks match (or completely go against) your own. It should make for some fun discussion!

And, with that, here are my picks...

1. When Harry Met Sally (1989) - I'm with Luke 100% on this. Billy Crystal and Meg Ryan are magic together, and have the kind of spark you rarely see in movies. An amazing, insightful, endlessly quotable film that, for my money, best showcases two people falling in love.

2. Love Actually (2003) – 8 interweaving love stories, all wonderful (my personal favorites are Bill Nighy’s rock-star “epiphany,” and Liam Neeson’s stepson’s first love). I could watch this all the time too...but it’s even better during Christmas!

3. Pride & Prejudice (2005) – Okay, this is a bit of a cheat since it’s not a standard romantic comedy, but it’s one of the most romantic things I’ve ever seen...and it’s pretty funny at times (plus, it’s a killer adaptation of one of my favorite books, so I have to squeeze it in). Keira Knightley shines in this (and deserved that Oscar nomination), and Matthew McFadyen might never live down his Mr. Darcy. As much as I love the BBC mini-series, this is hands-down my favorite version of this story.

4. Four Weddings and a Funeral (1994) – One of Hugh Grant’s best films, and the one that first made him a star (it’s also from the same people who gave us “Love Actually” and “Notting Hill”). The writing is sharp and moving, and the performances are all perfect (particularly Kristen Scott Thomas as the sardonic, but heartbroken best friend, and John Hannah as a gay man dealing with a sudden tragedy). It just gets better the more you watch it.

5. Forgetting Sarah Marshall (2008) – My pick for the best movie from the Judd Apatow camp. Star Jason Segel’s script is smart and downright hilarious at times, and, on top of all of that, seems to come from a very real place. (This and “Eternal Sunshine of the Spotless Mind” are really two of the best films about getting over break-ups.) Lots of laughs, lots of heart, and great performances all around (especially Segel, Mila Kunis, and the scene-stealing Russell Brand).

6. Hannah and Her Sisters (1986) – Easily one of Woody Allen’s (that master of clever dialogue and relatable human situations) finest films. Tracing the stories of Hannah (Mia Farrow) and her extended family, it’s funny at times (Woody Allen’s courtship and disastrous first date with Dianne Wiest) and painfully real at others (Michael Caine’s storyline) - this is really a must-see. Only Woody Allen can capture so much life in less than two hours.

7. Wimbledon (2004) – This is not a great film...but, man, is it charming and rewatchable. It also combines two of my favorite things: the great Paul Bettany (so good as Geoffrey Chaucer, the "herald", in “A Knight’s Tale”) in his first real leading role, and tennis (in fact, some of the very best ever put on film). Bettany’s terrific here as an underdog player (in a role that might have been far less interesting with a different actor), and Dunst shows that she can be pretty lovely when she’s not forced to whine through an entire “Spider-Man” film. A cute romance, an even better acting showcase, and some excellent tennis sequences—my DVD player is much too familiar with this one.

8. How to Steal a Million (1966) – An oldie, but very much a goodie. Case in point: screen goddess Audrey Hepburn at her most luminous, Peter O’Toole (one of the very best actors alive) in a sprightly, very funny performance, an adorable romance, and a very clever heist to boot. Check this one out—it’s a delight from start to finish.

9. The Princess Bride (1987) – This one’s just full of imagination and memorable laughs. It looks like a standard swashbuckler from the outside, but William Goldman’s script (adapted from his own novel) is clever and consistently enjoyable to watch. Filled with iconic supporting work from Mandy Patinkin (who owns one of the best movie lines ever: “Hello, my name is Inigo Montoya. You killed my father. Prepare to die.”), Billy Crystal, and the late Andre the Giant, and all anchored by the great romance between Cary Elwes and the beautiful Robin Wright Penn. By the way, I think this will make a great double feature with “Stardust” (which I had to exclude since it can’t fit into the romantic comedy category), if anyone’s curious to try...

10. Clueless (1995) - Don't be fooled by that ultra-pink DVD cover - this is a clever, very witty film, and Alicia Silverstone couldn't be more adorable as Cher, the pampered Beverly Hills princess who tries to make her life mean something more. (Oh, and just in case you didn't know, she and her best friend, Dion, are both named "for popular singers of the past who now do infomercials"). As a high-school movie, it's sweet and extremely quotable (Cher's recital of the last line of "A Tale of Two Cities" is priceless). As an adaptation of Jane Austen's "Emma" (yeah, seriously), it's pitch-perfect - it's one of my favorite reworkings of any classic story, and catching the Austen similarities and updates is a huge part of the fun. Also check out Paul Rudd as Cher's sarcastic, "kind of a Baldwin" step-brother, Brittany Murphy in one of her first big roles, "Scrubs" star Donald Faison as a hilarious, supposedly-macho boyfriend, and Breckin Meyer as the sweetest, most loveable stoner since Sean Penn's Spicoli.

And, sorry, you guys - I have to squeeze in just one more...

11. Pretty in Pink (1986) – The late, great John Hughes only wrote the script for this, but his touches are all over the final product: the relatable, awkward teenagers, that cool soundtrack, and, of course, the memorable characters and romance. Basically, it's a love triangle between Andie (frequent Hughes collaborator, Molly Ringwald), a hip girl from the lower side of the class-scale, her goofball best friend, Duckie (Jon Cryer), and the rich (but actually pretty nice) Blane (Andrew McCarthy). There’s also a fun, oily, “villainous” turn from a young James Spader, and an ending that lots of people don’t agree with...but, to me, it all feels very right. It’s a charmer of a movie, and the entire experience is a joyful trip through the heyday of Hughes-dominated high-school classics.

Image courtesy of Universal Pictures.