The Best Music Moments From ‘Overcompensating’ 

Britney Spears, “Lucky”

Episode: “Lucky”

The oldest track in the show’s playlist is Britney Spears’ shimmering gem “Lucky.” It first floats in during a childhood sleepover scene with young Benny and his friends. The song returns to score a college move-in montage—Benny, now a closeted gay jock, packing his bags under the weight of high parental expectations. But “Lucky” isn’t just background noise; it becomes a quiet anthem of rebellion. As the first episode closes, the song swells during Benny’s first real act of defiance: ditching his carefully charted path to impulsively enroll in a film studies class—just to sit closer to his crush. A glittery pop ballad becomes his coming-of-age battle cry.

Far East Movement, “Like A G6” / Nicki Minaj, “SuperBass”

Episode: “Who's That Girl”

One of the show's most side-splitting moments? The pregame before the infamous night at the rock bar. In a desperate attempt to blend in with his new “bros,” Benny endures them rapping the straightest, most cringe-inducing frat anthem of all time: Far East Movement’s “Like a G6.” It’s all energy drinks and fragile masculinity—until Benny decides he can’t take another second of “feelin’ so fly.” He hijacks the aux and drops Nicki Minaj’s “Superbass.” The boys go silent and rigid as a statue as Benny flawlessly spits every single bar of Nicki’s tongue-twisting masterpiece, not missing a beat. And just like a great pop hook, the song returns in episode two’s final scene—this time softer, sweeter—after Benny and Carmen (Wally Baram) share a heart-to-heart that that lays the foundation of a real friendship.

My Chemical Romance, “Welcome to the Black Parade”

Episode: “Welcome to the Black Parade”

The crown for Most Emo Moment™ in the show? No contest—it goes to Grace, absolutely obliterating My Chemical Romance’s “Welcome to the Black Parade” in a dingy hometown bar, surrounded by her opps. It’s the Thanksgiving episode, and Benny, Grace (Mary Beth Barone), and Carmen are back in their small Idaho town, colliding with ex-crushes and the ghosts of awkward teen years. Grace, now nicknamed “Disgraced” by the locals is barely holding it together—until Carmen, freshly aware of Grace’s emo past, sneakily signs her up for karaoke.

What follows is pure cinematic catharsis: Grace stomping the stage. The bar is stunned. Carmen’s jaw is on the floor. Meanwhile, in the most on-brand B-plot ever, Benny is making out with a boy (for the first time) in the bathroom. It’s messy, emotional, iconic—your classic coming-of-age cocktail. 

Charli XCX Medley

Episode: “Boom Clap”

Charli XCX’s chaotic fingerprints are all over Overcompensating—she even pops in for a guest appearance in the aptly titled fourth episode, “Boom Clap.” Her music threads through the series, from “Vroom Vroom” to the dreamy yearning of “Party 4 U.” But no Charli moment hits harder than her live performance of “I Love It.”

Sure, show-Charli is less than thrilled to be playing a college gig, but once she hits the stage, she’s pure pop power, commanding the crowd. The audience is fully losing it—singing, dancing, borderline frothing. Enter Hailee (Holmes), the show’s reigning queen of chaos, who’s been counting down to this concert like it’s her Super Bowl. Overcome by the moment, she jumps onstage like a crazed fan and tells looks Charli that, without her music, she would’ve unalived herself. 

Charli doesn’t miss a beat. “Bitch… what the fuck?” she snaps, equal parts horrified and hilarious before jumping right back into the song. It’s unhinged and iconic, and perfectly captures Charli’s comedic chops—and Hailee’s complete lack of chill. Instant rewatch. 

Wiz Khalifa, “Black and Yellow“

Episode: “Black and Yellow”

Why are college a cappella groups always unintentionally hilarious? That’s the question echoing in my head after watching Overcompensating. The show repeatedly wheels out the campus a cappella crew to deliver pitchy, straight-faced renditions of songs like “Trap Queen” and—brace yourself—a full-on Chief Keef medley. The choreography is stiff, the harmonies ambitious, and yet, somehow, it’s mesmerizing. 

But the crown jewel of cringe arrives when the group earnestly performs Wiz Khalifa’s “Black and Yellow” at a tailgate, clearly convinced they’re adding gravitas to the pregame festivities. It’s a “we have Glee at home” moment so off-key it takes a beat to even recognize what song they’re attempting. 

Still, there’s something weirdly endearing about how seriously they take it. Their total commitment to the bit, whether intentional or not, adds a surreal layer of comedy that the show wisely doesn’t undercut.