When you think of romantic gestures in movies, numerous iconic moments come to mind, but what about when they’re set to specific music? In Ry Russo-Young’s upcoming romantic drama, The Sun is Also a Star, the lead character of Natasha (Yara Shahidi) realizes she’s falling for Daniel Bae (Charles Melton) after the two visit a karaoke bar. As Daniel sings “Crimson and Clover,” Natasha starts envisioning her life with him, all through the power of a pop song.  

This led me to ponder other times in movies someone’s made a grand gesture through the use of music. Now, keep in mind, I’m looking at something highly specific for fun. The characters in question have to use a song, either singing or playing, in order to convey their feelings toward another character (thus, musicals where everyone sings don’t count).  


Here are the nine that immediately came to mind:  

1. ‘In Your Eyes’ – ‘Say Anything’ (1989)


This is the gold standard of romantic musical gestures and to not include it would set the list off on the wrong foot. The film’s protagonist, Lloyd (John Cusack) has just lost the love of his life, Diane (Ione Skye). He commits to standing outside her bedroom window blasting Peter Gabriel’s “In Your Eyes.”  

Is it a scene that’s been endlessly parodied and criticized for how dated it is? (Lloyd ain’t exactly taking no for an answer.) Yes. But, that being said, it’s still utterly amazing. Cameron Crowe’s feature spends a significant amount of time presenting Lloyd as the perfect boyfriend. He writes Diane letters, is respectful to her, and generally is a man you’d want to spend your life with. And in this moment he’s completely destroyed, desperately hoping that just reminding her of what the song means to them – it was playing after they lost their virginities – will be enough. It isn’t, and the movie takes some more bumps to get to the happy ending. But Lloyd Dobler and Peter Gabriel will always become synonymous with musically inclined romance.  


2. ‘You Outta Know’ – ‘Booksmart’ (2019)

This is a bit of a cheat since Booksmart hasn’t been enjoyed by the masses and it’s a very small scene in a movie all about putting yourself out there. That being said it’s a fantastic scene and shows how scary showing your real self can be. Sometimes you have to hide behind the music and sing your heart out.  

Amy (Kaitlyn Deaver) is desperate to get the attention of a girl she’s been crushing on all year. So on the last night of school before graduation Amy and her bestie, Molly (Beanie Feldstein) go to a party. As Amy gets progressively drunker she decides to take her crush up on a little karaoke, belting out this angry Alanis Morissette song. Not only is Amy able to show her crush how cool and fun she is – she is doing this for her after all – but Amy can finally let loose. She uses the excuse to sing not only to declare her feelings, but to finally be herself.  


3. ‘I Wanna Grow Old With You’ – ‘The Wedding Singer’ (1998)

This Adam Sandler-starring 1980s throwback was one of the most suggested features for this list. Sandler’s Robbie Hart spends the entire movie bemoaning his love life – he was dumped by his fiancee at the altar – before he finally realizes he’s head over heels for Julia (Drew Barrymore). The problem is the film puts her on a plane to Vegas where she’s going to marry a terrible guy.  

Every element of a classic romance is here: a race against time, someone doomed to marry the wrong person for them, and the grand gesture happening in front of an audience. In this case, Robbie finally discovers the inspiration to write an original song, which he performs for Julia on the flight they’re both on (with a little help from rocker Billy Idol!). The fact that Robbie’s song is darling is one thing, but the sheer joy from the rest of the crew is also fantastic. They’re so in love with love that they help Robbie practically take over the plane to get to Julia. It’s a moment of pure sweetness that could only happen in a movie.  


4. ‘Never Had’ – ’10 Years’ (2011)


Not many people remember this little indie drama from 2011, and it’s a shame because it’s cast is stacked with everyone from Channing Tatum to a pre-Guardians Chris Pratt. But the movie’s best moment comes courtesy of the internet’s boyfriend, Oscar Isaac (yep, he’s in this, too). 10 Years follows a group of friends coming back together for, you guessed it, their ten-year high school reunion. Oscar Isaac’s Reeves has become a successful musician but he’s still pining for the shy Elise (Kate Mara), who doesn’t know much about his newfound life other than he’s famous.  

Reeves finally gets his moment to declare his love by singing the song that’s made him a superstar which, as we find out through the lyrics, is actually about Elise! It’s cliché as can be but who doesn’t want to have Oscar Isaac write a song about them? It’s a moment meant to sweep any girl off their feet and it definitely has maximum swoon impact.  


5. ‘(Don’t You) Forget About Me’ – ‘Pitch Perfect’ (2012)


So far these moments are pretty dude-heavy, and maybe that’s because a certain amount of humility has to happen during these moments that are just easier to envision with male characters. Then again, Anna Kendrick’s Becca is hard-headed throughout all of Pitch Perfect, so it’s understandable that her big moment involves her proving her love through song. 

During the Bella’s final performance at Nationals, Becca finally gets a chance to sing the songs she wants. She brings all her acapella ladies together for one big performance and also sees it as her chance to show Jesse (Skylar Astin) she loves him. She starts singing the theme song from The Breakfast Club, proving to Jesse that she actually watched a movie he loves all the way to the end. (Yeah, their relationship is odd.) As Jesse raises his fist in the air, á la Judd Nelson, it proves that he accepts her apology and that he feels the same. Who knew acapella could be so compelling? I’ll see myself out.  


6. ‘Can’t Take My Eyes Off You’ – ’10 Things I Hate About You’ (1999)

10 Things I Hate About You turns 20 this year and contains one of the, if not the, ultimate romantic gesture. As Joseph Gordon-Levitt’s Cameron says to Heath Ledger’s Patrick, in order to win Kat (Julia Stiles) Patrick must “sacrifice yourself on the altar of dignity and even the score.” How does he do that? By taking over the school’s marching band to introduce his rendition of the Four Seasons’ “Can’t Take My Eyes Off of You.”  

It’s a moment that every teenage girl mooned over for a combination of reasons. For starters, Ledger totally plays the scene with a solid mix of confidence and embarrassment. He knows what he’s doing is dumb, but he understands it’s the only way to prove to Kat that he cares. Conversely, Kat’s look as she walks forward holds those same emotions. She’s certainly embarrassed, but she’s completely touched anyone would make a complete fool of themselves for her. Each of the characters knows what the other needs and, without saying anything other than the lyrics of the song, prove how compatible they are for each other.  


7. ‘You Were Meant For Me’ – ‘Singin’ in the Rain’ (1952)

I know I said no musicals, but what Stanley Donen’s Singin’ in the Rain does is a bit of meta-romance, lifting the veil off how movies create love to put two characters together. In this case, mega moviestar Don Lockwood (Gene Kelly) wants to show his attraction to ingenue Kathy Selden (Debbie Reynolds). He does that by starting off with the “proper setting,” showing how lights and wind can create a dreamy fantasy landscape perfect for wooing. Eventually he sets the right tone, giving way for him to express his love for Kathy in song. Anyone willing to rig a movie set to make someone feel special deserves a spot on this list!  


8. ‘Town Without Pity’ – ‘Look Who’s Talking’ (1989)

More often than not these moments are about making someone feel embarrassed but strong enough to persevere because the rewards are worth it. This also means one half of the couple is left to stare in awe, or shock, or some other emotion but never really do anything. Thankfully we have Amy Heckerling’s 1989 rom-com to give us two active participants. 

In this case, single mother Mollie (Kirstie Alley) is trying to both entertain new son and have some of fun of her own by dancing around her kitchen. Babysitter/cabbie James (John Travolta) sees all this and decides to show his flirting skills by throwing her apartment door open to start crooning this Gene Pitney classic. It’s a moment that’s hilarious and romantic, as Mollie tries to act like she doesn’t care before James makes her dance with him. The two are literally joined together, leading to a saucy moment that proves these two will be together by the end for sure.  


9. ‘It Had to Be You’ – ‘A League of Their Own’ (1992)


One of only two women to have one of these moments on the list, I’d be remiss not to include the boozy Megan Cavanaugh as Marla Hooch in this baseball drama. She starts off the movie almost failing to make the All-American Girls Baseball League because the scout doesn’t think she’s pretty. Throughout the movie the men, either on-screen or announcing the games, give Marla grief for not being attractive. 

So when she decides to go out with the girls to a roadhouse called the Sud’s Bucket it’s assumed nothing will happen. But thanks to a dress and “a lot of liquor,” Marla apparently becomes a completely different woman. Leader Dottie (Geena Davis) finds Marla crooning the Ruth Etting standard, “It Had to Be You” to a bar patron named Nelson, who, in a fit of subversion, is the one sighing and swooning over her. This moment is not only hilarious, but it’s amazing how director Penny Marshall takes the grand gesture and uses it to give Marla not just agency, but independence. For once she feels attractive and has that attractiveness reciprocated by Nelson. The two end of marrying because it had to be them. 

The Sun Is Also A Star is in theaters this weekend. Get your tickets here.

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