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10 Awkward Celebrity Prom Photos

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Long before the Grammys and blockbuster deals, these stars were just teenagers sweating through prom night like everybody else.

TheThings Celebrity’s countdown “10 Funny Celebrity Prom Photos” digs up the kind of pictures most people would pay good money to keep buried — the ones taken before the red carpets, before the multi-platinum albums, back when a bad date and a rented tux were the biggest problems in the world. The video runs through ten now-famous faces caught in full teenage-formalwear panic, and the gap between who they were then and who they became is the whole joke.

• Taylor Swift’s prom photo shows her posing in typical mid-2000s formalwear next to a date who looks openly indifferent to the camera.
• Jennifer Aniston’s throwback picture pairs a puffy strapless gown and voluminous ’80s hair with visible braces, alongside a date in a full vest-and-bowtie set.
• The countdown covers ten pre-fame prom photos total, leaning on outdated fashion and stiff body language rather than glamour shots.

Taylor Swift’s Pre-Fame Prom Night

Years before “Fearless” made her a household name, Taylor Swift was just another teenager posing for the obligatory prom picture. The photo featured in the countdown shows her smiling brightly for the camera while her date appears far more interested in the lens than in her — a classic teenage-photo mismatch that has aged into internet gold now that she’s a multi-platinum act. Swift’s dress reads as standard mid-2000s formalwear, nothing that hints at the arena-filling career waiting a few years down the line.

It’s the kind of split-screen moment that fans of stars like Beyoncé and other artists who went from unknown teenagers to global names find endlessly relatable — the subject of plenty of similar retrospectives on musicians who turned out nothing like they seem once the spotlight hit.

Jennifer Aniston’s ’80s Time Capsule

Aniston’s entry is the countdown’s clearest “blast from the past.” The future “Friends” star shows up in a poofy strapless gown, big teased hair, and a mouth full of braces — three details that instantly date the photo to a pre-fame, pre-Rachel-Green era. Her date matches the retro energy with a fully coordinated vest-and-bowtie combo, the kind of formalwear choice that made sense in the moment and mortifying in hindsight.

She can be seen wearing a poofy strapless gown with big hair and braces — and the two of them look like they just stepped out of an ’80s time warp.

The Rest of the Countdown

Swift and Aniston aren’t the only recognizable faces in the lineup. The video also runs through Justin Timberlake in a white tuxedo jacket with slicked-back hair, Beyoncé in a matching green dress and hat with a date in a coordinating tie, and Rihanna in a pink satin dress paired with a curly hairstyle. Demi Lovato’s date turns up in a bright orange tuxedo jacket, Lady Gaga’s photo leans gothic with a black veil and crown, and Bruno Mars appears in a straightforward blue suit and bow tie.

Rounding out the ten: Katy Perry in a simple pink dress with a flower in her hair, and Ellen DeGeneres in a powder-blue tuxedo jacket paired with a date in a matching powder-blue dress. None of the photos are scandalous — they’re just teenagers in rented formalwear, which is exactly the point.

It’s a theme that keeps resurfacing across entertainment coverage of famous faces’ early years, not unlike stories tracking celebrities who crossed paths long before anyone knew their names.

Enduring Resonance of Social Awkwardness

What makes the countdown work isn’t the fame gap by itself — it’s how familiar every single photo looks. Mismatched dates, dated tuxedo colors, hairstyles that made sense for exactly one decade: these are the same details sitting in millions of family photo albums, just with a famous face attached. TheThings Celebrity built the whole segment around that recognition, betting that viewers will laugh at Aniston’s braces or Swift’s indifferent date because they’ve got a nearly identical photo of their own tucked away somewhere.