13 Amazingly Awkward Celebrity Prom Photos

With high school prom just around the corner in most American states, we thought it’d be fun to take a step back in time and see what some of our favorite stars looked like on their big night. These are 13 of the the most amazingly awkward celebrity prom photos. Honestly, we think the 80’s were a great decade for embarrassing photo ops.

1. Matthew McConaughey

McConaughey proves he was just as cute in the 80s as he is today. Here’s the American Hustle actor attending Longview High School’s senior prom. He was even awarded “Most Handsome” at the end of the night. The prom picture surfaced on Internet after McConaughey won the Oscar for his role as Ron Woodroof in Dallas Buyers Club and his prom date’s niece uploaded the pic with the caption “My aunt’s high school prom date just won an Oscar. Congrats, Matthew McConaughey!”

2. Danielle Fishel and Lance Bass

Corey didn’t take Topanga to prom? Nope, the former Boy Meets World star took her N’Sync boyfriend Lance Bass. Yes, the pair dated from 1999-2000 and Fishel had to ask Bass to the dance to make sure his schedule was free. Check out the adorable 90s couple complete with chunky heels and frosted tips.

3. Taylor Swift

Are you even surprised that the “Bad Blood” singer wore a dress that resembled a wedding gown to her Tennessee high school’s prom. We bet she wrote a song about her date too. But we have to admit that T-Swift does look gorgeous in this throwback picture.

4. Jessica Alba

We’re not sure what the theme of Jessica Alba’s high school prom was, but we at least hope there was a theme, because that is one interesting prom dress choice. Alba attended Claremont High School and graduated early at age 16. She went on to attend the Atlantic Theater Company.

5. Brad Pitt

Pitt grew up in Missouri attending Kickapoo High School, where he was a member of the golf, swimming and tennis teams. He also participated in the school’s Key and Forensics clubs, school debates, and in musicals. Sounds like a pretty well-rounded student to us. The Fury actor wore a grey suit and his signature smile to his 1981 high school prom.

6. Bruno Mars

The “Uptown Funk” singer attended President Theodore Roosevelt High School in Honolulu, Hawaii. Bruno, who went by his given name Peter Hernandez at the time, was heavily involved in music throughout school and even performed in his own band, The School Boys. The 29-year-old crooner looks adorable matching his lei with his date’s fuchsia dress, and can’t forget that afro!

7. Rihanna

Rihanna never graduated from her Barbadian secondary school, as she dropped out after moving to NYC to pursue her musical career. However, in 2007 a super-fan invited Rihanna to his high school prom and the “American Oxygen” singer accepted. Rihanna showed up as the surprise date for Richard in MTV’s reality series, Once Upon a Prom and the teen admits he was “awestruck.” Rihanna spent the night dancing, mingling with Richard’s friends, and even posed for an awkward prom photo.

8. Blake Lively

Lively filmed The Sisterhood of the Traveling Pants between her junior and senior years at Burbank High School. She also attended her high school’s senior prom wearing a sparkly pink gown complete with a diamond tiara like a Disney princess. It’s fitting because she was elected her class’ prom queen that night.

9. Jimmy Fallon

Look how adorable The Tonight Show host looked at his Saugerties High School prom in the early 90’s. The funny man even shared his own awkward prom story with his viewers saying, “My date went tanning the night before. I did not. I looked like Powder.”

10. Taylor Lautner

The Twilight heartthrob looks young and innocent in this Valencia High School prom photo with his spiky hair and cheesy grin. Besides attending school dances, Lautner balanced karate and acting with being on the football and baseball teams at his school, as well as participating in jazz and hip-hop dance classes.

11. Jennifer Aniston

The Cake actress is hardly recognizable in this classic 80s prom photo, complete with big hair and attitude. Aniston attended Manhattan’s Fiorello H. LaGuardia High School of Music & Art and Performing Arts, where she joined the school’s drama society. We think the actress looks better today at 46 than she did in her teens, but this picture is priceless.

12. Beyonce

The “Flawless” singer attended Alief Elsik High School in Houston, Texas. Beyonce went to her high school’s prom with her boyfriend at the time, Lyndell Locke. The couple was together for nine years before he lost her to Jay Z. We love Bey’s colorful cut-out dress with thigh-high slit. Her personal style hasn’t changed too much over the years. We’re just wondering if it was made at home by the House of Deréon?

13. Will Ferrell

Are you even surprised by who’s wearing the tiara in this picture? Will Ferrell was a clown even back in high school. He won “Best Personality” his senior year. The Get Hard actor attended University High School in Irvine, California. Besides making his classmates laugh, Ferrell was very involved in sports. He was a kicker for the school’s varsity football team, a forward on the soccer team, captain of the basketball team, as well as a member of student council.