My Ten Favorite Romantic Comedies

I'll admit it, I've been on kind of a "RomCom" kick as of late (which is, thankfully, giving way to a "bad horror film" kick as Halloween draws nearer). I don't consider myself to be overly sentimental, but I enjoy a good romantic tale every now and then. Here are 10 of my favorites: 

10 P.S. I Love You

I’m secure enough in my heterosexuality to admit this: Gerard Butler (Dear Frankie) is a sexy, sexy man. Not only is he a very good looking guy, but he also has that deep, authoritative voice and an undeniable warmth about him. Unfortunately, his character dies five minutes into the film, but he still remains a constant presence throughout the film, having planned out a series of romantic surprises for his widow, played by Hilary Swank, prior to his death. Jeffrey Dean Morgan (Watchmen) and Harry Connick, Jr. (Hope Floats) show up as potential suitors for the widow Swank. Now, ordinarily I cannot abide Mr. Connick, as he invariably plays the unnervingly suave pretty-boy type. But in this film, he's the troubled, weird, dorky guy, and that in and of itself makes him infinitely more likable. Plus, the end result of his and Ms. Swank's attempt at romance is both sweet and hilarious. 

9 Just Friends

As a man well-acquainted with the “Friend Zone,” it’s nice to see it addressed in comedic fashion. Ryan Reynolds plays a guy who was the fat kid in school and had an unrequited crush on his best friend, Jamie (Amy Smart). After a humiliating experience at his graduation party, he swears to better himself and over the years becomes a suave, svelte womanizer with a high-paying job in the record industry. Through a series of “random” events, he is forced to return to New Jersey for Christmas, where he reconnects with family, friends . . . and Jamie. This is complicated by a fellow suitor named Dusty Lee (formerly Dinkleman, played by Chris Klein), a beaming, guitar-strumming EMT whose charm knows no bounds. This is a fantastic comedy with some great performances and some truly hilarious visual gags (if you like tasers, sports violence and holiday decorations that burst into flame, you’ll like this one).

"You're laughing now, but soon I'll be a Green freaking LANTERN!"

8 The Third Wheel

If ever there was a romantic comedy for guys, this is it. Stanley (Luke Wilson) has a crush on Diana, the new girl at work (Denise Richards). He purposes in his heart that he’s going to ask her out. A year passes. Then another. Finally, though, he learns she’s just exited a relationship, and if he’s going to ask her out, there is no better time. With some encouragement from his best friend (Ben Affleck), he finally works up the courage and invites her to dinner and a show, and she accepts. Stanley is elated, and his friends and coworkers secretly place bets as to how well the date will go. Everything goes smoothly until Stanley accidentally hits a pedestrian, Phil (Jay Lacopo), who they end up taking to the hospital. But Phil’s not done with them yet, and wherever they go, they keep running into Phil. The question is, will this third wheel ruin their date or bring them closer together? Wilson, Richards, Affleck and Lacopo turn in some great performances here, as does an uncredited Matt Damon as Richards’ smarmy, smirking ex. It’s a sweet, heartfelt film that will truly have you cheering for the underdog.

Well, isn't this cozy . . .

7 Stranger Than Fiction

To set the record straight, Blades of Glory is the best Will Ferrell movie ever. But it's not the best movie starring Will Ferrell ever (there's a difference); that honor goes to Stranger Than Fiction, a quirky, thoughtful film about Harold Crick, a nebbish IRS agent who leads a sad, solitary life and one day realizes he has a narrator in his head (with a British accent, no less!). S**t gets real when said narrator announces Harold is about to die. The rest of the film is essentially a subdued version of The Bucket List, in which Harold decides to live out his few remaining days to the fullest. He takes a break from work, learns to play guitar and ultimately, inadvertently, falls for Ana (Maggie Gyllenhaal), a fiery Marxist baker who he happens to be auditing. Alas, they have a bit of a falling out, but he makes up in the most perfect way in the history of the universe:

SO. MUCH. WIN.

Anyway, there aren't a whole lot of movies that can make me cry, but this one has managed it a few times. Without spoiling too much, Harold eventually accepts his fate, and what happens next is so shocking, so unfair and so truly heart-rending that a happy ending seems impossible. 

*SPOILER ALERT*

It's not! 

6 The Wedding Singer

Just as Stranger Than Fiction isn't exactly a Will Ferrell movie, The Wedding Singer isn't exactly an Adam Sandler movie. Sure, there's some off-color, childish humor in parts (especially in the Special Edition), but if you look closely, past the pervy old ladies, drunken best men and butt-grabbery, there's a really thoughtful love story hiding just beneath the surface. Sandler plays the titular role, Robbie, a sweet guy who loves his job. Drew Barrymore plays Julia, a waitress at the venue he plays at. They're both engaged . . . but then Robbie gets dumped the altar (while an orchestral version of "Don't Stop Believin'" plays in the background). Julia feels sorry for him and they start spending time together, with him reluctantly helping her plan her wedding to Glenn (who turns out to be an absolute jackass). After a series of misunderstandings, Julia agrees to fly with Glenn to Las Vegas to get married, and Robbie is left alone to grieve over another missed chance at love. He confides in his best friend, Sammy, a womanizing limo driver played by Allen Covert (Mr. Deeds, Grandma's Boy), and tells him he wants to be more like him--a different woman every night. And then Covert steals the show. The subsequent happy ending borrows a bit too much from "Crocodile Dundee," but it does involve Billy Idol, so there's that. 

And Steve Buscemi . . . because Steve Buscemi.

5 My Man Godfrey

This is the oldest film on my list, but don’t be fooled; it might be from the 1930s, but it still holds up today. It’s essentially the story of a rich girl who takes a homeless man off the street and gives him a job as the family butler, and his attempts to make sense of the crazy, dysfunctional household he’s been brought into. William Powell is one of those great leading men of the olden days who never really got his due. He’s not conventionally handsome, but his cool, unflappable presence and quizzical brow give him a unique charisma all his own. Also consider Carole Lombard as the blonde, ditzy leading lady, Irene Bullock, a sweet, childish girl who genuinely cares about Godfrey’s well-being and only late in the film admits that her concern is more than that. Another comedic standout is Mischa Auer as Carlo, the constantly eating “protégé” of Mrs. Bullock, who is more than willing to humiliate himself for the family’s amusement if it means continued access to the refrigerator and its contents. 

The things I have to do to get a sandwich around here . . .

Aside from the screwball humor in and of itself, the movie retains its relevance today in that it is a product of the Great Depression. Now more than any other time since then, we as Americans can understand and relate to the financial troubles of the era, and the struggle between the haves and the have-nots resonates well into today.

4 Pride and Prejudice

This is a very polarizing opinion, but I’m going to share it anyway. I’ve seen the old-school, half-a-day-long BBC production of Pride and Prejudice, starring Colin Firth and Jennifer Ehle, and frankly, I’m not a big fan. I mean, it’s good and all, but it’s lacking in spark, and Firth seems to mistake Mr. Darcy’s lack of social skills for a lack of emotion altogether. Firth is a bland block of wood onscreen, which severely diminished my enjoyment of the film. That said, I absolutely love the 2005 version, starring Matthew MacFadyen and Keira Knightley (with Rosamund Pike as Jane Bennet . . . mmmmm). It’s a much more condensed version of the classic Jane Austen romance, but what it lacks in depth (which isn’t much, all things considered), it more than makes up for with its characters. Donald Sutherland absolutely nails the dry wit of Mr. Bennet. Brenda Blethyn is suitably obnoxious as the meddlesome Mrs. Bennet. Jena Malone personifies the dotty, foolish and entirely oblivious Lydia Bennet. Dame Judi Dench is manipulative and downright sinister as Lady Catherine de Bourg. And Tom Hollander absolutely nails the role of the odious parson Mr. Collins. 

Why yes, I am an odious little toad. Thank you for noticing.

Then we have our leading man and lady. MacFadyen excels where Firth failed. He plays Darcy as callous and standoffish, but there is warmth and sincerity in his eyes. He is not without a sense of humor, although it takes serious effort to extract it from him. And when he finally professes his love for Elizabeth, the emotion pours out like a tidal wave despite his apparent calm. Knightley’s Elizabeth, too, is a nearly perfect adaptation of Austen’s iconic character. Feisty and flippant, she takes severe offense to Darcy’s initial coldness and holds it against him for most of the movie. Their game of emotional cat-and-mouse is handled superbly, and to put it bluntly, despite the modest dress and moral propriety, the sexual tension between the two is unbelievable. They don’t even kiss until the very end, but it’s the scenes wherein they almost kiss that stand out. The film provides that delightful sense of “will they or won’t they?”, although any reader worth his or her salt knows they will.

A THOUSAND TIMES YES!

3 You’ve Got Mail

When one thinks of great Nora Ephron movies, Sleepless in Seattle is usually the one that springs to mind. It’s a good movie, with some great chemistry between stars Tom Hanks and Meg Ryan, but their reunion nearly a decade later is actually a far superior movie, despite sharing a nearly identical plot. Hanks and Ryan play rival business owners who are also—unknowingly—engaged in an anonymous email affair. In person they exchange barbs and plot each other’s destruction while confiding in each other and discussing Austen online. Costars Heather Burns, Steve Zahn, Greg Kinnear and Parker Posey are top-notch, and there’s also a golden retriever named Brinkley, so what’s not to like? The film also has a fantastic soundtrack, including Harry Nilsson, Roy Orbison, The Cranberries and Louis Armstrong, which is yet another reason to enjoy it.

"Wait, what are you doing? That caviar is a GARNISH!" 

2 While You Were Sleeping

Bill Pullman is one of those great, underrated actors who can play the dork (Sleepless in Seattle), the jerk/nutcase (Mr. Wrong) or the president (Independence Day), but very rarely does he get to play the romantic lead. While You Were Sleeping remedies this wonderfully. Pullman plays Jack Callahan, the strapping heir to an estate furniture company owned by his father, Ox (the ever-cantankerous Peter Boyle). And Jack is in love with his comatose brother’s fiancée, Lucy (Sandra Bullock). What he doesn’t know is that Lucy and his brother have only met in passing, and she’s afraid to tell his family the truth for fear his grandmother will keel over dead. Hilarity ensues, along with more misunderstandings. By all rights, it should be a terrible movie, but the actors, who also include Jack Warden, Michael Rispoli and Peter Gallagher, are quick-witted and clever, and there is a great mix of one-liners and visual gags to go along with the surprisingly competent script. It’s one of the highlights of the seemingly endless supply ’90s romantic comedies, and it’s one my mom and I have watched over . . . and over . . . and over again.

"We know you're in there, Lucy. JOIIIIIINNNN USSSSSSS!"

1.  As Good As It Gets

This is also my all-around favorite movie of all time. Directed by James L. Brooks (director of Broadcast News and producer of TV shows like Taxi and The Simpsons), this film is a truly fulfilling study of human nature and the winding path to redemption. Jack Nicholson—he of the deviously arching eyebrows and predatory grin—stars as Melvin Udall, one of the most loathsome characters in film history. He’s rude, fastidious and bigoted, and has no filter whatsoever. Worst of all, he doesn’t care. He uses his obsessive-compulsive disorder as an excuse to avoid human interaction and is content to while away the hours locked in his apartment, hammering out flowery works of romantic fiction that belie his cruel nature. But, slowly but surely, Melvin is forced to come out of his shell and learn to relate to other people, starting with the gay neighbor he torments (Greg Kinnear) and the longsuffering waitress he abuses (Helen Hunt). Just as gradually, we begin to see how damaged and in pain Udall himself really is under his abrasive surface. And then, out of nowhere, what started out as a biting character study blossoms into a love story, and it works. The film manages to end on a hopeful note, with Udall literally taking his first step toward rediscovering his own humanity and overcoming his personal faults. In my opinion, it’s the best movie ever made, and I will gladly debate that point with anyone. 

"Who's an ugly little dustmop? Yes, YOU are!"

HONORABLE MENTION: Intolerable Cruelty. 
From Raising Arizona to Fargo to O Brother, Where Art Thou? to No Country for Old Men to True Grit, I love the Coen Brothers. And I love this strange, cynical romance between a strange, cynical divorce lawyer (George Clooney) and the manipulative yet oh-so-beautiful Catherine Zeta-Jones, who marries womanizers and then takes them for everything they've got when she divorces them. I didn't particularly like this movie when I first saw it, but over the years I've really come to appreciate it. Plus, there's a hearty dose of Simon and Garfunkel in the soundtrack, and that's always a good thing. There are some great performances in this film, not just from the romantic leads but also from the likes of Richard Jenkins, Billy Bob Thornton, Cedric the Entertainer and Geoffrey Rush, who is absolutely hilarious in the opening scene. Plus, look sharp for the Bruce Campbell cameo appearance. All in all, it's a great movie, and one of my favorites.

"You fascinate me!"