Beloved teen comedy Bring It On turns 20 today, which means, yes, “I’m sexy, I’m cute, I’m popular to boot!” has been in our cheer lexicon for two decades. Sure the script included iconic lines and that spirit fingers scene, but the brightest spot in the film’s legacy comes in the form of one Cliff Pantone, a young man with a lopsided grin and penchant for rock ‘n’ roll. Played to perfection by Jesse Bradford, Cliff was always the best of the teen heartthrob of the late nineties/early aughts bunch. (I’m looking at you, literally any character played by Freddie Prinze Jr.) Cliff was the kind of smart, supportive, and sexy high school boyfriend that became a barometer for future romantic partners. In short, Cliff is perhaps the last remaining timeless teen movie crush.
Hundreds of young actors auditioned for the role, Jason Schwartzman and James Franco among them (the latter passed when Freaks and Geeks was picked up as a series). But it was Bradford’s personality, along with his easy and essential chemistry with lead actress Kirsten Dunst as head cheerleader Torrance Shipman, that sealed the deal. Director Peyton Reed told Buzzfeed in 2015 that the actor encapsulated everything Cliff was supposed to be: “[Bradford] had the perfect blend of being a good looking kid, a really smart actor, and you bought him as a kid who was into punk music.”
Nostalgia certainly helps keep connections with the characters we loved growing up, but it’s not just a trip down hormone-fueled memory lane that makes Cliff’s allure enduring. He possesses perpetually coveted qualities of a terrific partner: support (he attends all of Torrance’s cheerleading events despite being nonplussed about the sport), unyielding belief in her, and confidence (remember that car wash scene?). The fact that Cliff and Torrance were opposites in terms of interests, style, and personalities taught a teenage me that it’s not necessary to have everything in common with a partner. Like the best teen movies do, their coupling defied typical high school culture’s assumption that the popular girl and the alt boy don’t fit.
The teen entertainment boom of the late ‘90s and early 2000s provided young viewers with a wealth of leading men to lust after. Each boy had different characteristics and attributes but compared to his genre peers, Cliff was the Goldilocks of the group, striking just the right balance of sweet and edgy. He was far less dangerous than 10 Things I Hate About You’s Patrick Verona (who may or may not have eaten a live duck). With his retro band t-shirts and self assured vibe, he was infinitely cooler than The Princess Diaries’ Michael Moscovitz (what was this Genovian Independence ball look?). He was significantly more thoughtful than Never Been Kissed’s Guy Perkins. Cliff was the most compelling love interest by virtue of his three-dimensional characterization, replete with quirks and the ability to evoke emotional resonance. Meanwhile the personalities of Zack from She’s All That (Freddie Prinze Jr.) and Cameron from 10 Things (Joseph Gordon-Levitt) amounted to little more than jock and nerd stereotypes, respectively.
Cliff, in retrospect, even exhibited the kind of Good Guy behavior you’d want from a current paramour: He didn’t push Torrance into breaking up with her longtime boyfriend. As a romantic adolescent obsessed with Bring It On and as a similarly inclined woman in her 30s, it’s easy to award Cliff top spot in the pantheon.
Speaking of Torrance's longtime boyfriend, Aaron (played by the late Richard Hillman)—whose interests included gaslighting and sleeping with other girls—his dorm room poster collection alone is proof that Cliff was just cooler than the other high schoolers at Rancho Carne. Aaron celebrated Sugar Ray and Hootie and the Blowfish; Cliff was a quintessential aughts pop-punk dude. His vibe was more bubblegum skater boy than leather jacket and cigarettes. More Sum 41 than Stones. (Though Bradford did previously suggest to EW that Cliff may have wound up dead from a drug overdose in his later years... Let’s hope he was being sarcastic.)
Cliff’s look was also always A+. (I’m severely disappointed that today’s alt boy uniform has been reduced to the far-more-muted hipster aesthetic.) Adorably, Bradford even bought Cliff’s The Clash t-shirt (used as a talking point in his first scene with Torrance) himself to ensure sartorial authenticity. Cliff was never without a studded bracelet or beaded chain necklace; he wore headphones looped rebelliously around his neck in the hallways at school.
But Cliff’s pièce de résistance of swoon was recording a song for Torrance on his guitar. (Imagine my disappointment to learn it wasn’t really Bradford singing the seminal ‘Just What I Need’.) As the original groupie and writer Pamela De Barres once mused, “I dig musicians. I feel they have the most to offer me mentally and emotionally.” Cliff was a non-threatening, starter version of the rocker archetype, ideal if you were a teenage girl discovering your sexuality and forming an identity.
Who can forget Torrance accidentally-on-purpose stumbling into Cliff’s bedroom during a sleepover with his sister Missy (Eliza Dushku)? A pajamas-clad Cliff behaves ridiculously as he scissor kicks and wails on his guitar, while unbeknownst to him, Torrance watches him from the doorway, thoroughly charmed. The memorable scene speaks to the relatable longing we have all felt for the classmate with the worn-out Converses and bicycle chain resting against his hip. It’s a lovely time capsule to revisit. In adulthood, these kinds of precarious and sweetly juvenile moments of courtship are no longer a facet of our dating experiences. Instead, Cliff Pantone will always be a teen dream, suspended in nostalgic animation but still capable of promoting the most intense feels.
And if you’re in the market for a palpable Hollywood kiss, Torrance embracing Cliff by grabbing his neck during Bring It On’s uplifting finale is enough to make you applaud...through jealousy, of course.