This Valentine’s Day, let us transport you to an eternally romantic place. Where school dances are a near weekly affair; where kisses are backdropped by Chagall art installations; where the greatest sign of affection is spending all your college tuition on a gift of diamond earrings; where everyone, even a Porsche-driving Prep named Jake, probably has the entire Smiths discography memorized. Come with us to Shermer, Illinois: the fictional home of the John Hughes coming-of-age rom-com.

We curated a playlist of love songs, culled from the prolific writer/director/missionary-of-British-New-Wave’s considerable cannon of soundtracks, to set a magically (if not mawkishly) ’80s mood for your February 14th.

For the opening track, we reach outside of Hughes’ series of quintessential teen films for a choice deeper cut: Frank Sinatra’s “Strangers In The Night”, featured in 1983’s Mr. Mom. Allow the velvet voice of Ol’ Blue Eyes ease your chalky candy heart as we prepare to enter the five year period (1984-1987) when Hughes dwelled in high school angst and infatuation. The Smith’s wistful “Please Please Please Let Me Get What I Want” sets the tone in a number of Hughes’ films (if not the entirety of the ’80s teen genre). Most memorably, an instrumental version plays in the museum scene of Ferris Bueller’s Day Off.

I like to refer to the next three tracks as the Tender Trio. We have General Public’s “Tenderness” (Weird Science); Code Blue’s “Whisper/Touch”, with a repeating chorus of, “whisper/touch/tender/cruel” (Pretty In Pink); and Otis Redding’s “Try A Little Tenderness” (also Pretty In Pink). If you’re rolling solo this V-Day, the Tender Trio can provide a solid soundtrack for swiping right on Tinder. Just a thought.

Duckie’s (John Cryer’s) unforgettable lip-sync to “Try A Little Tenderness” is his best, though not his only, musical moment in the film. Also notable is when a love-sick Duckie croons a wilting rendition of “Love”. You will find John Lennon’s original on our list. This naturally leads us to “If You Leave” by Orchestra Manoeuvres In The Dark, from Pretty In Pink’s prom scene, where selfless Duckie urges Andie (Molly Ringwald) to rekindle her relationship with Blane (Andrew McCarthy). This leaves Duckie heartbroken and abandoned at the prom. But only for a moment, because this is the ’80s and we demand a happy ending, so Duckie is immediately rewarded with an ’80s babe.

Hughes famously lamented this ending. He originally had Andie choose Duckie, but rewrote the ending at the studio’s behest, after his ending did not test well with audiences. Only a year later, Hughes released Some Kind of Wonderful, essentially retelling the story of Pretty In Pink, but with his original ending intact. At the emotional climax of the film, Lick the Tin’s cover of “Can’t Help Falling In Love” plays as Watts and Keith walk down the street, hand in hand. For our playlist, we return to the Elvis Presley original.

In the middle of the playlist is a block of the moody new wave you’ve been expecting. Echo and the Bunnymen’s “Bring On the Dancing Horses” (Pretty In Pink), The Dream Academy’s “The Edge of Forever” (Ferris Bueller), New Order’s “Thieves Like Us” (Pretty In Pink), and, of course, a track immortalized by its association with The Breakfast Club, Simple Minds’ “Don’t You Forget About Me”. 

Money Talks’ “Tiny Little Heart Attack” (from 1991’s unloved Career Opportunities) and The Divinyls’ punkish “Ring Me Up” (Sixteen Candles) are two tracks that, in my opinion, don’t enter the conversation of great John Hughes songs nearly as often as they should (maybe because they aren’t so inseparable in our memories from the scenes that feature them). Here they are side-by-side for you to enjoy, followed by “Modigliani (Lost In Your Eyes)” by Book of Love; a track we found outside of teen flick territory, on the soundtrack for Planes, Trains and Automobiles.

One of the most beloved scenes from any Hughes film is the cake scene from Sixteen Candles, set to the breathy, synthy “If You Were Here” by The Thompson Twins. Here’s a hypothetical question: would “If You Were Here” have survived past the ’80s if not for this scene?

We transition now to Van Halen’s cover of Roy Orbison’s “Oh, Pretty Woman”, used in Weird Science to accompany Kelly’s jaw-dropping strut through the mall. [writer’s bragging note: My mom’s cousin, Bill Dees, wrote and performed the original “Oh, Pretty Woman” with Orbison]. Released in the same decade as the original “Oh, Pretty Woman” was Darlene Love’s “(Today I Met) The Boy I’m Gonna Marry” and The Association’s groovy “Cherish”. Two decades later, the first would be featured in Sixteen Candles and the second in Pretty In Pink.

We have now reached the last slow song of this school dance, so steel your nerves and ask your crush to join you on the floor for Spandau Ballet’s fantastically corny “True” (Sixteen Candles).

You’ll remember Sigue Sigue Sputik’s Clockwork Orange-sampling “Love Missile F1-11” from Ferris Bueller’s opening monologue (“Life moves pretty fast… yadda yadda yadda”). While it hardly qualifies as a love song, it’s just too much fun not to include on this list. A more fitting inclusion would be Wayne Newton’s “Danke Schoen”, which Ferris croons into the shower head during the same monologue. This classic track of fond remembrance also seems like an appropriate note to bookend a Valentine’s playlist that began, 22 songs ago, with Sinatra.

How’d we do? What tracks would you add? Which would you remove? How angry are you that I excluded Oingo Boingo? Somebody always gets angry about Oingo Boingo. Let us know in the comment below, and have a very Shermer Valentine’s Day.