Why did I ask our ScreenRant team of music experts to pull together a list of seemingly upbeat songs that are actually heartbreaking or twisted underneath?

Because I’m a diabolical editor with a taste for emotional whiplash. Think Anna Wintour (sans those tired Hermès scarves) in vintage Beats by Dre.

The truth? Sometimes the most gutting lyrics are hiding in plain sight—buried beneath disco beats, power chords, or featherlight pop vocals. Music doesn’t always need a sad piano ballad to wreck you. It can sucker-punch you with a glittery hook and leave you dancing through your existential crisis.

So, when I assign a list like this, it’s not just to mess with the team (though… perks). It’s because these are the songs that sneak up on you. The ones that prove music doesn’t just soundtrack our joy… it helps us survive the mess in between.

“Millie Pulled a Pistol on Santa” – De La Soul

The sped-up sample of “I’ll Stay” by Funkadelic gives De La Soul’s 1991 song, “Millie Pulled a Pistol on Santa” an upbeat, almost danceable feel, but it’s far from a dance tune. Instead, it tells the dark tale of Millie, who was being sexually abused by her father, an admired school social worker, who played Santa Claus at Macy’s.

The group members rap about Millie not caring for her father, which baffled them because he seemed to be such a wonderful person. Their confusion only grew when Millie began missing school. More so, when she asked Trugoy, one half of De La Soul, if he could get her a gun.

Millie eventually came clean to Trugoy about what she was experiencing, and she ended up getting the gun from someone else. Then at the end of the song, Posdnuos, De La Soul’s other member, sees Millie stroll into Macy’s while taking his younger brother to see Santa, and she guns her father down. – Daryl Nelson

“Escape (The Piña Colada Song)” – Rupert Holmes

“This is the cheesiest song I’ve ever heard in my life,” I thought, when I was listening to “Escape (The Piña Colada Song)” play in Shrek (2001) as the Magic Mirror was playing matchmaker with Lord Farquaad. It wasn’t until years later that I realized what the bouncy music was hiding.

Make no mistake; this is a song about cheating. Somehow, with the jaunty guitar and drums leading into the first verse, it’s easy to overlook the fact that the very first lyric is “I was tired of my lady / We’d been together too long.” The entire song is about this man responding to a personal ad in the newspaper (it’s an old song) so he can have an affair away from his wife. The fact that the ad was placed in the paper by his wife, also hoping to cheat, is pure coincidence.

“Escape (The Piña Colada Song)” supposedly has a happy ending, but that’s just because the dark, gross implications of this wacky mix-up are swept under the rug in a way that feels exactly like a romantic comedy. – Owen Danoff

“Santeria” – Sublime

‘90s ska punk legends Sublime are certainly no strangers to upbeat, feel good, beachy stoner rock. Their renowned self-titled album is full of breezy tracks that sound like they’re meant to be enjoyed on the sand with some sort of mind-altering substance in hand. The album’s second single, and arguably their greatest hit, “Santeria,” embodies that feeling more than most.

The way Bradley Nowell softly coos the chorus, “What I really wanna know / Ah, baby, / What I really wanna say / I can’t define,” is enough to soothe anyone, and make all their worries disappear. In reality, however, this song is about rage and getting revenge on an ex-girlfriend who cheated, and the man with whom she cheated.

Nowell sings about wanting to “Pop a cap in Sancho,” the man that his ex-girlfriend, Heina, cheated on him with, and “Slap her down,” too, using Chicano slang names that mean rival lover and queen. While upon first listen, this song sounds just like the beachy upbeat hits Sublime is known for, the lyrics are much darker than the sound would suggest. – Lacey Cohen

“Born In The U.S.A.” – Bruce Springsteen

While I often call it a toss-up between this song and Woody Guthrie’s “This Land Is Your Land” due to their similarly misunderstood nature, “Born in the U.S.A.” is a twilight shade darker in subject matter. How it continually became part of melodic political campaign discourse or the patriotic soundtrack to fireworks displays at baseball games is beyond my logic.

That’s because with “Born in the U.S.A.,” Bruce Springsteen is painting a wearied irony. His character is born at the bottom of a supposed land of opportunity and is stuck there, opting to fight in the Vietnam War to avoid jail time when he gets into trouble. He then finds this dead-end conflict doesn’t end when he comes home.

Beneath a triumphant synth-rock beat and an iconic chorus beats the heart of a narrator who feels unknown, lost, and forgotten by his country. It’s the blue-collar struggle felt by so many of Springsteen’s characters, with a typical brand of dark desperation overtaking the red-blooded love of country. – Chris Hedden

“Jump” – Van Halen

When thinking of songs that channel happiness and joy, you cannot go past Van Halen’s “Jump.” An arena-rock triumph that smashed its way to #1 in 1983, those punchy, ecstatic fleuro synths have long been shorthand for a certain aspirational reach-for-the-sky attitude that characterized the ‘80s.

However, there’s a sad story that inspired this anthem. David Lee Roth spoke of the song’s iconic refrain, “Might as well jump!” He’d taken inspiration from a TV news report on a suicidal man who contemplated jumping off a building. Canily, though, Roth repurposed its dark inspiration into an uplifting message about taking a leap of faith. – Angus Thomas Paterson

“Hey Yah” – OutKast

Possibly one of the catchiest songs of the 2000s, OutKast’s “Hey Ya” is not as cheery as it may seem. Iconic lines like “shake it like a Polaroid picture” mask what Outkast’s leading man, André 3000, is actually singing about: a failing relationship. The first verse vaguely reveals the strained relationship at the center of the hit song.

Though it’s the hit’s second verse that unveils the coming apart as the singer asks himself if nothing lasts forever, “then what makes love the exception?” It’s actually pretty deep for a song mainly remembered for its “hey ya” chorus.

Lyrics about denying their own unhappiness reveal a few more cracks in the foundation, before the song goes in a different direction. OutKast further avoids the crumbling love story in a catchy outro that has listeners more focused on its silly lyricism than the deep sadness hidden beneath the surface. – Gina Wurtz

“Help!” – The Beatles

“Help!” is an upbeat, catchy song that’s loads of fun for all The Beatles fans to sing along with. But if you listen to the lyrics, it’s really a cry for help. John Lennon, who wrote the lyrics, found himself struggling with his mental health. He’d become rich and famous rather quickly and just didn’t know how to cope.

Lennon and McCartney wrote the song not long after meeting Bob Dylan, who encouraged the duo to start writing from the heart. They wrote the song, “Help!” for the movie of the same name, but Lennon reported later that the words came out of him because he was in pain. – Jason LeValley