An Ode To The Crooked, Gapped, And Gloriously Imperfect Celebrity Teeth Of The ‘90s And ‘00s

Once upon a time, in the gloriously unfiltered world of the ‘90s and ’00s, Hollywood smiles actually looked like they belonged to human beings. 

Before the age of blinding veneers and identical pearly whites, celebs hit the red carpets and our screens proudly rocking the teeth they were born with — a little crooked, maybe a bit gappy, sometimes even a tad yellow. They weren’t perfect, but they were real.

Fast forward to today, and we’re living through an epidemic of ultra-straight, ultra-white, ultra-samey teeth. The natural smile is practically an endangered species — although a few stars (looking at you, Zendaya and Aimee Lou Wood) are still proudly flying the flag for the originals.

So, in loving memory of the era of beautifully imperfect celebrity smiles, here are 18 stars who rocked their natural teeth back in the day… and what their grins look like now.