Top Ten Romantic Comedies: A Valentine’s Day List

By Lisa Anderson

I Love You Phillip Morris

The romantic comedy: it’s the most reviled of genres, and yet also the most resilient. There’s an assumption that men only go see them out of obligation . . . although men are likely to enjoy the good ones, and women are likely to dislike the bad ones. Too many rom-coms rely on mutually insulting stereotypes (the commitment-phobic man, the miserable career woman), predictable plots (boy meets girl, boy does something stupid), and problematic supporting characters (Sassy Black Friend, Sassy Gay Friend).

Nevertheless, they keep getting made, and they keep making money. This is because among the scores of bad rom-coms, there are gems. Almost everyone can think of a few that have actually made them laugh, and managed to resonate with their feelings and experiences. Here are a few of mine, in no particular order.

While You Were Sleeping (1995)

This is one of the more traditional choices on my list. Sandra Bullock plays a transit employee named Lucy who has a crush on a polished, successful man she sees every day. He ends up in a coma, and his bubbly, loving family mistakes her for his fiancée. By the time the movie is over though, she has fallen in love with the man’s brother, played by Bill Pullman. I love this movie because it is set at Christmastime, and because of the importance of the family to the story. I also love that Lucy passes up up the wealthy, flashy brother for the competent but down-to-earth one who would usually be set up as the Baxter. She chooses the Baxter quite literally, in fact: Pullman’s character from Sleepless in Seattle was the origin of the term.

Intermission (2003)

This movie, which tells the interconnected stories of several Dublin residents, isn’t necessarily billed as a romantic comedy. Love and relationships are on everyone’s mind, though, and couples form, break up, and reconcile (several characters are part of more than one couple.) This is one of the funniest movies I’ve ever seen, and it includes such familiar faces as Colm Meany, Colin Farrell, Kelly MacDonald, and Cillian Murphy.

Keeping The Faith (2000)

A young priest and Rabbi who have known each other their whole lives fall in love with the same woman. What is this, some kind of joke? Well, the priest is the only one who walks into a bar, but—yes, it is, and a funny one at that. This laughs come courtesy of Ben Stiller, Edward Norton, Jenna Elfman and the incomparable Anne Bancroft. I like it not only for such romantic lines as “God was showing off when he made you,” but also for the way it takes seriously issues of faith and spirituality in a changing, multicultural world.

I Love You Phillip Morris (2009)

Jim Carrey and Ewan McGregor star in this true story of a con man who falls in love with a fellow inmate while in prison. Distribution was held up until recently due to MGM bankruptcy proceedings. I’ll warn you now that the end is not “happily ever after,” but both actors have a gift for humor and tenderness. The scene where they slow-dance together in their cell while chaos erupts around them on the block is breathlessly funny.

Imagine Me and You (2005)

Do you believe in love at first sight? What if you found it on your wedding day, with someone other than your spouse? Piper Perabo plays a new bride who comes to question not only her marriage, but also her sexuality, when she falls for Luce, a florist played by Lena Headley. I struggle with the infidelity aspects of this movie, but as with Philip Morris, it is refreshing to see a well-done, mainstream treatment of same-sex relationships. This movie has a stellar secondary cast as well, including Anthony Stewart Head and Matthew Goode, and treats them (especially Goode, the Baxter) with much more respect than rom-coms often do

Benny and Joon (1993)

I know I have said that Johnny Depp plays too many oddball characters, but this role came early in his career, and is a long way from Willie Wonka. Here he plays Sam, an eccentric young man who comes to live with a mentally ill young woman (Mary Stuart-Masterson) and her brother (Aidan Quinn). While Joon’s mental illness is never specified, I appreciate the message that the mentally atypical have a full spectrum of needs, and that love is not just for the “normal.” Depp’s Buster Keaton routine is also a small legend in cinematic history

It’s Complicated (2009)

In this film, Meryl Streep plays a divorced woman with grown children who starts an affair with her now-remarried ex-husband. As if that weren’t, well, complicated enough, a more available man, played by Steve Martin, takes interest in her, too. While the ending isn’t exactly surprising, the emotions of everyone involved, including the children, are realistically complex. It’s also pleasing to see a love story involving people old enough to be grandparents. Streep and Martin are wonderful as always, and while I have issues with Baldwin as a person, he has an amazing comic talent.

High Fidelity (2000)

This movie is a real cultural touchstone. John Cusack plays Rob, a record store owner whose girlfriend Laura is breaking up with him because he hasn’t changed since they met. He retraces some of his worst breakups to find out what went wrong. In the end, this movie is about Rob and Laura’s passage into adulthood as well as their romance, and it is that passage that brings them back together. The movie would be worth seeing if only for the music geekery, especially Rob’s advice on making a mix tape. Jack Black, Joan Cusack, and Tim Robbins also appear in hilarious supporting roles.

Scott Pilgrim vs. The World (2010)

Like High Fidelity, this one wasn’t billed as a romantic comedy, but part of what I’m trying to do here is point out how broadly the term can be defined. Love is certainly the motivation of the title character, as he battles his erstwhile girlfriend’s seven evil exes for her hand. This movie has a sort of 21st-century Magical Realist style, and is chock full of gaming references. While the romance may not stick with you, its lessons about growing up and conducting your love life with integrity will.

Love at First Bite (1979)

You will never see George Hamilton paler than when he plays Dracula. I loved this movie as a child, just because I love vampires, but it wasn’t until I saw it again last year that I realized how subversive it is. The Count goes to the United States in search of the reincarnation of Mina, only to find that his virginal flower is now a hard-drinking, foul-mouthed, sexually liberated starlet. If you enjoyed the Rifftrax to Twilight, this film is perfect for you.

A you can tell, I’m a fan of the romantic comedy genre, although I’m picky about it. The best romantic comedies are the ones where the characters are three dimensional and non-stereotypical, and get together because they want to, not because of any manipulation or dependency. It also helps if the secondary characters—family, friends, co-workers—are also believable, and if the action takes place against a well-drawn background of the leads’ non-romantic lives.

Feel free to name your own favorite romantic comedies in the comments. Happy Valentine’s Day from Popshifter, however you are spending it!