Cinema’s Most Romantic Music Gestures

From Tom Cruise’s boisterous performance in Top Gun to Christian Grey’s weird rendition of “Maybe I’m Amazed” in the recently released Fifty Shades Freed, movie characters have used music to express romantic feelings for as long as we can remember. Serenades don’t always work, but they’re always memorable. So we decided to put together a list of cinema’s best, weirdest, and most awkward music-based expressions of love to take a look at how romantic gestures have changed over the years, if at all. Beware of spoilers!


Say Anything (1989)

The serenading-someone-with an-emotional-song trope probably wouldn’t exist if it weren’t for Say Anything. Even if you’ve never seen the movie, you’re probably familiar with the scene in which Lloyd Dobler (John Cusack) stands outside Diane Court’s (Ione Skye) window with a boombox, the strains of Peter Gabriel’s “In Your Eyes,” inevitably annoying Diane’s neighbours to no end. “In Your Eyes” was playing when Lloyd and Diane first hooked up, so we guess the gesture is kind of sweet? The fact that Lloyd is willing to risk a possible noise complaint makes us wary about how reliable he’d be as a long-term boyfriend, though.


Scream 2 (1997)

In Scream 2, Derek (Jerry O’Connell) serenades his new girlfriend Sidney Prescott (Neve Campbell) with The Partridge Family’s “I Think I Love You” in the middle of their college cafeteria. It’s an amusing scene, but before long Derek gets captured and Sidney gets caught up a murder spree that suspiciously resembles the one she survived in the first Scream movie. All in all, Derek’s gesture is cute but a little obnoxious. It still has an important place in cinematic romantic gesture canon, however, as Tom Cruise’s Top Gun serenade inspired Derek to sing to Sidney in the first place.

10 Things I Hate About You (1999)

A sincere, well-planned romantic moment has the potential to melt the heart of a true cynic, even when that cynic is the defiant, stubborn Kat Stratford (Julia Stiles). Patrick Verona’s (Heath Ledger) dramatic performance of Frankie Valli’s “Can’t Take My Eyes Off You” in 10 Things I Hate About You doesn’t completely win Kat over, but it does convince Kat to forgive him for rejecting her attempted kiss the night before. The attempt at reconciliation is a little over-the-top, but that’s part of what makes it so great—by singing and dancing in front of Kat’s entire soccer team, the closed-off, surly Patrick proves that he’s willing to open up and make a fool of himself to earn back Kat’s trust. He also does it to fulfill the deal he’s got going on with Joey Donner, but Kat and Patrick end up together so let’s just forget about that part of the story, shall we?

P.S. I Love You (2007)

In this mid-2000s tearjerker, an Irishman, Gerry (Gerard Butler), falls in love with an American, Holly (Hilary Swank). So it’s only natural that Gerry sweeps Holly off her feet with his rendition of “The Galway Girl,” an upbeat ditty that American rocker Steve Earle originally recorded with Irish folk artist Sharon Shannon. Not to be confused with Ed Sheeran’s “Galway Girl,” “The Galway Girl” tells the story of a man who falls in love with a black-haired, blue-eyed girl from Galway. Sure, it’s a little on-the-nose, but the movie uses it to effectively establish how hard it is for Holly to move on after Gerry passes away.


Easy A (2010)

Easy A is clearly meant to be an informal love letter to John Hughes’ 1980s high school romps. The movie’s final scene—in which Todd (Gossip Girl’s Penn Badgley) blasts Simple Mind’s “Don’t You Forget About Me” while sitting atop a lawnmower—is overt enough to put any doubts about said love letter to rest. Olive (Emma Stone) can’t resist Todd’s Breakfast Club homage and agrees to join him as they ride his lawnmower off into the sunset. And the magnetic pull of “Don’t You Forget About Me” is undeniable, so we’ve got to applaud Todd’s song choice even if it is a little obvious.


Blue Valentine (2010)

Blue Valentine’s Dean (Ryan Gosling) and Cindy (Michelle Williams) have one of the most tumultuous on-screen relationships we’ve ever seen. Dean awkwardly jamming and singing along to The Mills Brother’s “You Always Hurt the One You Love” while Cindy tap dances by his side nevertheless makes us root for them to get together, even though we know their relationship will eventually fall apart. Dean’s song isn’t loud or flashy, but it endears Cindy to him right away, proving that good things sometimes come in dorky, ukulele-strumming packages.


Friends with Benefits (2011)

Friends with Benefits came out at the height of flash mob-mania, meaning that the synchronized dance routine Dylan (Justin Timberlake) arranges to impress Jamie (Mila Kunis) doesn’t age particularly well. With that being said, Dylan’s choice to set the routine to Semisonic’s “Closing Time” is pretty clever (Dylan and Jamie fight about whether or not “Closing Time” is a Third Eye Blind song throughout the entire movie). Plus, Dylan and Jamie’s banter about not being able to hear each other over the music is a sweet nod to impractical romantic movie clichés.


Pitch Perfect 2 (2015)

We could have picked a song from the first Pitch Perfect movie which, like Easy A, involves someone using “Don’t You Forget About Me” to win over a potential love interest. Instead we went with the goofier Pitch Perfect 2 so we could highlight the scene in which Fat Amy (Rebel Wilson) shout-sings pat Benatar’s “We Belong” to a skeptical Bumper (Adam DeVine). Amy sings part of the song while gliding down a lake in a tiny rowboat—she could have just walked around the lake, but as Beca (Anna Kendrick) points out, “Fat Amy doesn’t do anything small.” And her dedication pays off, as she and Bumper end up aggressively making out and rolling around on the grass when she reaches shore.


Trainwreck (2015)

When it comes to on-screen displays of affection, the guy almost always takes the lead. But in 2015’s Trainwreck, Amy (Amy Schumer) is the one who serenades Aaron (Bill Hader). Amy apologizes to Aaron (Amy is trying to get him back after they broke up) by dancing to a diverse combination of songs, including Redfoo’s “Let’s Get Ridiculous,” 2 Unlimited’s “Get Ready for This,” and the aforementioned “I Think I Love You.” Amy’s inclusion of  “Uptown Girl” is what really sells the scene, however, as both she and the viewers learn that Billy Joel’s ‘50s-inspired track is Aaron’s favourite song earlier in the film.

Apparently using music to woo someone or proclaim one’s love always involves a song that’s at least a couple decades old. But Amy Schumer high-kicking her way through “Uptown Girl” is lightyears away from Lloyd Dobler silently and stubbornly holding up a boom box until Diane agrees to get back together with him.

Music-based romantic gestures have indeed, evolved—they’ve taken almost 30 years to evolve, but it’s still progress. Hopefully they continue to evolve (seeing a female-led serenade that’s not played for laughs would be nice) and hopefully we continue to see gestures that are sweet and well-received rather than pushy and unwanted.