February 14 is around the corner, and whether you know it as “Valentines’ Day” or “Singles Awareness Day” (I’m in the latter category, thank you very much for reminding me), you’ll probably be in the mood for some good romantic comedies.

Now, there have been countless great rom-coms over the years—there’s everything from cross-dressing mishaps in Shakespeare’s As You Like It to verbal sparring in Jane Austen’s Pride and Prejudice to Charlie Chaplin’s endearing Little Tramp in City Lights, to Fred Astaire and Judy Garland’s expert twirling in Easter Parade—all the way up to spirited discussions of anti-depressants in this year’s critics’ darling Silver Linings Playbook.  In fact, there are so many out there that I thought I’d narrow this top-5 list down to contemporary selections from the past twenty years.

 

5.     Mean Girls (2004)
Mean-GirlsMean Girls is not your typical high school movie—it has a higher IQ than you might expect.  After all, the screenplay was written by Tina Fey—the same woman who called out Quentin Tarantino as “the star of all my sexual nightmares” at the Golden Globes last Sunday.

A pre-crazy Lindsay Lohan stars as Cady Heron, a previously homeschooled student experiencing high school for the first time. The film also features Fey herself as a harried calculus teacher, Rachel McAdams as devious Regina George, Lacey Chabert as insecure Gretchen Wieners, and Amanda Seyfried as the infamously dumb Karen Smith.

One of the things that makes Mean Girls such a great film is that behind all of the seemingly absurd remarks and situations, it’s a really real film.  Did you know that Queen Bees and Wannabes (the book that inspired Mean Girls) was a non-fiction self-help book?   When it really comes down to it, Mean Girls is not much of an exaggeration—not even the brawl with the Safari sound effects.  Anyone who’s ever been a teenager can relate.
 

4.     Clueless(1995)
CluelessIf you like modern takes on classics (think Ten Things I Hate About You and She’s the Man) it’s pretty much a given that you’ll love Clueless.  In this fairly faithful adaptation of Jane Austen’s Emma, Alicia Silverstone stars as Cher (no, not that Cher), a girl who delights in matchmaking (and shopping). Clueless also features a young Paul Rudd, whom Cher describes as “sort of a Baldwin,” a doe-eyed Brittany Murphy before things started to go downhill (too soon?), and for fans of Scrubs, a young and orthodontically-challenged Donald Faison.

Like Mean Girls, it’s a smart film—Amy Heckerling’s expertly written Valley Girl dialogue alone is enough to make you giggle.  Add to that a Jane Austen-based plot and horrendous 90s fashion and you’ve got yourself what might just be a classic in the making.
 

3.     Sleepless in Seattle  (1993)
Sleepless-in-SeattleWhen we’re talking romantic comedies, we’ve got to talk about Nora Ephron—a true master of the genre.  Sleepless in Seattle centers on Sam Baldwin (Tom Hanks), a sensitive architect still mourning his late wife, and Annie Reed (Meg Ryan), a reporter who sometimes abuses her access to information—we’ll let that slide, though, in the name of True Love. The two have good chemistry together—apparently Ephron agrees, as she cast them together again in You’ve Got Mail, another great film.

Part of the magic behind Sleepless in Seattle—what really sets it apart from all of its peers, is the fact that Hanks and Ryan share mere minutes of screen time.  We follow the two separately, the whole time hoping beyond hope that they’ll someday be united.
 

2.     Silver Linings Playbook (2012)
Silver-Linings-PlaybookEasily one of the best films this year—Jennifer Lawrence’s Golden Globe win and all of its Oscar nominations aren’t for nothing.  And I know people are skeptical of Bradley Cooper’s acting chops after seeing all of the smirking he does in the Hangover films, but he’s also great in this.

What’s wonderful about Silver Linings is that in addition to being a great romantic comedy, it’s also a family drama that deals with the implications of mental illness.  Director and screenwriter David O. Russell took this as a passion project; he adapted the screenplay for his son, who is bipolar, like Cooper’s Pat Solitano, Jr.  Russell writes from real experience, capturing both the difficulty and inner conflict of being bipolar (something Cooper does expertly—for the majority of the film he displays a palpable hatred, both for himself, and the illness which he struggles to control) and the complicated father-son dynamic in conjunction with it.

It should also be noted that Cooper and Lawrence have great chemistry—so great in fact, that the two newly-single stars already have the gossip mags buzzing.  Unfortunately, Cooper squashed these rumors without skipping a beat, telling reporters, “I could literally be her dad.”
 

1.     Love Actually (2003)
Love-ActuallyWhat makes Love Actually brilliant is its sprawling cast and complex web of interweaving subplots.  Pretty much every British actor who’s anyone made it into the film.  In that way, it’s a lot like Harry Potter.  If we’re going off that, Professor Trelawney (Emma Thompson) and Snape (Alan Rickman) play a troubled married couple in this film (both of them are fabulous, by the way.  If Emma Thompson doesn’t bring you to tears, then you don’t have a heart—like me).  There’s also Colin Firth who plays a newly single writer, who falls for his Portugese housekeeper, despite a language barrier that only allows for communication through mime, Keira Knightley as a newlywed with a smitten best man, a grieving Liam Neeson, forging a new paternal bond with his lovesick step-son (Thomas Sangster), and (for all you Sherlock fans) Martin Freeman as an adorably awkward adult film stand-in—a job that’s decidedly less sexy than it sounds.  To add even more dimension to the various levels of romance, it all comes together on Christmas Eve.

Love Actually is truly the one romantic comedy to rule them all—the tagline is suitably, “Love actually is all around,” and the movie acts as evidence to that.