Country singer Faith Hill will always look her best. With that elegant high-neck dress, it’s hard to believe that this was simply her high school prom and not some early red-carpet event. Granted, this would have been the mid-80s, and we have to admit that this picture looks like it’s straight out of a 60s photoshoot.
But hey, maybe Faith liked the vintage look back then. While some other awkward prom photos might embarrass some stars today, Hill looks perfectly classy, just as always. Her date could have put a little more pep in his step, but we’re sure the two still had a wonderful night.
Courtney Cox
This is an interesting look for Courtney Cox. While we acknowledge that this was the 80s and special concessions are made for this, the "Friends" actress sweater-dress-combination seems weird, even for then. We will say, though, that it is very on-brand for Monica Geller.
While she looks slightly strange, there's no doubt that she looks very happy, especially as she holds onto the arm of her sweet date. He, on the other hand, could have lightened up a bit. Maybe the photographer just caught him at a bad moment, but maybe he also didn't fully recognize the huge star potential in his date.
Debra Messing
Our beloved star of "Will and Grace" had her fun too. With that white satin dress, pearls, and 80s wave, Messing and her date (seen here mid-blink) are ready to awkwardly embrace the sweet sounds of Cyndi Lauper's "Time After Time." You don't really ever see someone mid-blink, do you?
This is quite a fascinating picture for a number of reasons. Who knew that years after this fun, innocent high school night, she'd be one of our favorite sitcom stars and a total gay icon? It just goes to show, kids, life doesn't end in high school! There is hope beyond the cringey yearbook pics.
Angelina Jolie
Angelina always struck us as someone who wouldn't actually go to prom, but this photo proves us wrong! Not only did she go, but she went all out with the lovely satin dress and an intriguing chunky necklace. Angelina seems to be sporting a makeup-free look, which obviously doesn't matter for her because she has glowing clear skin and pristine eyebrows.
We're not sure who got the golden opportunity to be Angelina's date to prom, but we bet that guy is still bragging about it today. Who knew that once upon a time, this was Hollywood's bad girl? We suppose things changed in later years because here, Angelina looks simply angelic!
Angela Bassett
You can't get any cooler than this. Angela Basset and her date do not look like they're in high school at all, though that marching band trombone brings us back to those high school days. Angela looks beautiful for sure, but we obviously need to pay due respect to her date who opted for a bold, all-white look.
That takes a big personality to pull off — so it's no wonder he scored the confidant Angela Bassett to accompany him. We simply love that 1970s cool, big hair, bellbottoms and all. It wasn't for many decades that you could match hairstyles with your prom date and no one would bat an eyelash.