This article previously ran in February 2014. We’re reposting for Valentine’s Day.
Tomorrow is Valentine’s Day, so that obviously means we’re supposed to watch syrupy romantic comedies and eat licorice and write love letters and make mixtapes and do anything and everything seen in a John Hughes movie. Truth? I love all that stuff. I’m a cynical bastard about pretty much everything — you should see me when the brunch line’s too long and my friends insist we wait; it’s like 10″ nails on a chalkboard — but when it comes to sensationalized love? I eat it up.
No surprise then that one of my favorite films remains Cameron Crowe’s Singles. Or that long before Napster and AOL, I once created an entire cassette of songs taped from similar fare I would catch on HBO or Cinemax by holding my Talkboy up to the TV speakers. (How else was I supposed to get The Boombox Song, as I once called Peter Gabriel’s “In Your Eyes”?) Of course, I’m a long sufferer of the Cusack Syndrome, where I remain convinced that the only way to a girl’s heart is through music.
So, tired of all the think pieces and negative lists around this time of year, I decided to focus on something positive: 10 songs that I’ve always thought could be solid romantic comedies. Like an idiot, I dreamed up a cast for each entry, wrote up a story based on the lyrics, and even included some smarmy taglines for good measure. It was fun playing Hollywood producer, okay?
If there’s anyone to blame for this, an editorial that some might consider a crime against humanity, I point to my mother and father. I’m pretty convinced my mother would cry at any of these films and that my father would even revisit a few repeatedly, sort of like he already does with Bandits, Wedding Crashers, and Bridesmaids. See where I get this obsession?
Happy Valentine’s Day, folks.
“Spin the Bottle”
The Juliana Hatfield Three
Cast: Emma Roberts, Channing Tatum, Billy Crystal, and Eric Roberts
Story: Struggling to pay college loans, Diana Lawrence (Emma Roberts) juggles three different jobs: a daytime waitress, a fashion writer, and a late-night bartender at a night club. When rising film star T.J. Banks (Channing Tatum) throws an event at the club, his party jokingly starts a risque game of spin the bottle. Seeing her advantage, Diana tosses a secret note inside the bottle, which tips off a rags-to-riches affair that lasts more than just five minutes in the closet. Naturally, his middling agent, Jackie Greaser (Billy Crystal), does not approve.
Tagline: “Bottom’s up!”
Does the band make an appearance? Hatfield plays the single mother of Emma Roberts and has a great scene with her estranged father, Eric Roberts, who charms critics in a telling role.
Happy ending? It’s up to the bottle.
Fun fact: This song appeared on another romantic comedy’s soundtrack — Ben Stiller’s Reality Bites.
Cast: Justin Long, Aubrey Plaza, Steve Guttenberg, and Louis C.K.
Story: Kansas-bred Devon Glory (Justin Long) has just accepted a job at a prestigious law firm in downtown San Francisco. While out celebrating alone, he befriends a narcoleptic college student named Sheila Green (Aubrey Plaza), who shows him how to be young amidst the wild sides of the city. The only problem is that she keeps passing out at random intervals, leaving him to his own devices. It’s Martin Scorcese’s After Hours meets Woody Allen’s Annie Hall in this midnight comedy about love at first snooze.
Tagline: “Walking free, come with me.”
Does the band make an appearance? Bradford Cox plays a heroin dealer in the Castro District, who leads them to the West Coast Drug Czars: Guttenberg and C.K. in a match that Entertainment Weekly’s Owen Gleiberman calls “delightfully tacky.”
Happy ending? Let’s just say there are zero nightmares for Plaza.
Fun fact: Deerhunter’s music has yet to appear in a Hollywood production.
Cast: Jake Johnson, Kerry Washington, Mindy Kaling, Idris Elba, Jr., Horatio Sanz, and Marc Maron
Story: Love is in Chaosville for Ted (Jake Johnson), who comes home to find his stuff outside his apartment and his now ex-girlfriend, Amy (Kerry Washington), opening her door for a new lover (Idris Elba). Shamed and confused, he uses Craigslist in a desperate attempt to find a last-minute roommate, Rhonda (Mindy Kaling), who eventually helps him find his dark side. The two plot a sick revenge plan that gets heartless with every move.
Tagline: “How could you be so…”
Does the band make an appearance? The only man Rhonda would marry is Yeezus. No cameo, but she carries a locket with his photo in it. Creepy, huh?
Happy ending? It all begins and ends on a Lovelines-esque talk show hosted by Marc Maron and Horatio Sanz. So, tune in to find out. (Spoiler: Yes.)
Fun fact: The song was used to great effect in the 90210 episode “Games People Play” back in 2008.
Cast: Greta Gerwig, Michael B. Jordan, Allison Brie, Sam Neil, Bonnie Hunt, and Wendell Pierce
Story: Eccentric NYU student Kristin Cook (Greta Gerwig) comes home from a two-month study in France, ready to marry her high school sweetheart, Charlie Wing (Michael B. Jordan). The two are set to wed in six months at St. Patrick’s Cathedral in New York City, a sacred reservation at a special place they’ve had set in stone for over three years. When Charlie breaks things off suddenly, Kristin’s life is spun around, and she turns to her best friend (Allison Brie) to find her special someone as the clock’s ticking.
Tagline: “This time, the bride’s saving the date.”
Does the band make an appearance? Annie Clark and Kristin are both stood up by a blind date, only to discover they were both set up for each other. Hilarity ensues.
Happy ending? Yes and no. Kristin must realize love isn’t in the air for her, but for her estranged parents (Sam Neil and Bonnie Hunt), much to the chagrin of their confused minister (Wendell Pierce).
Fun fact: The song’s title originally came from a catchphrase of Arrested Development’s Maeby Funke, who warded off Hollywood producers while attempting to make, you guessed it, cheesy rom-coms.
“You Only Live Once”
Cast: Lizzy Caplan, Dane DeHaan, Donald Glover, Ted Danson, and Michelle Pfeiffer
Story: For five years, sexaholic Wendy Strickland (Lizzy Caplan) has overseen an advice column for The Seattle Times. When her single mother (Michelle Pfeiffer) is diagnosed with lung cancer, she has a sudden change of heart about her lifestyle. She refuses to die alone and, instead, sets out to revisit her past affairs, which have all been popular column topics despite destroying her lovers’ public lives. Things get ugly (Ted Danson), bitter (Donald Glover), and educational (Dane DeHaan) as Wendy attempts to add some light in her life.
Tagline: “A 1,000 ways to please a man. Only one requires a plan.”
Does the band make an appearance? There’s a Strokes poster in Dane DeHaan’s room. Otherwise, no.
Happy ending? It’s an indie rom-com, which means there’s a level of ambiguity that reads either way.
Fun fact: The song’s cousin “I’ll Try Anything Once” superbly soundtracked Sophia Coppola’s 2010 nap Somewhere, including its gorgeous trailer.