33. Anna Kournikova
Wow, OK. Never mind, some people get all the luck.
I’m sure snagging an “American Boy” was actually no problem while sporting these things. Wish I could say the same for myself.
31. Lourdes Leon
Maybe having Madonna as your mom somehow makes all aspects of puberty less difficult?
30. Danny Glover
If ever a question about wearing braces with a turtleneck and mustache, the answer is yes, my friend. Wear all three.
29. Emma Watson
Oh, totally. Me too.
28. Niall Horan
His strategy is admirable, indeed: No one will notice the braces if you sport a massive fompadour (fauxhawk and pompadour combined).
27. Willow Smith
Hop up out the bed, turn your swag on, but please be careful not to forget your retainer.
26. Thomas Sangster
Getting the shit kicked out of us by love would’ve been a lot easier if we had all looked this adorable while wearing braces.
25. Dakota Fanning
Where she temporarily lacked in teeth, she made up in enthusiasm.
24. Nicholas Cage
23. Jaden Smith
Is there anything cooler than wearing braces with a vest? Yes, many things, but the boy pulls it off.
22. Emma Stone
Emma stone was seriously precious with braces, I was really counting on her to come through on this one.
21. Cindy Crawford
OK, so my orthodontist totally forgot to add that sparkle. Nbd.
20. Serena Williams
Beads. Just keeping adding beads.
19. Megan Fox
Wearing an uber-tan/sunburn helps braces look more subtle, if you ask me. Also, it helps if you’re just Megan Fox, period.
18. Kate Hudson
Still less awkward than me in middle school; I was on my third perm at this point.
17. Prince Harry
What on earth would we have done if paparazzi had followed us around in sixth grade? Flossed more, probably. But, probably not.
16. Vanessa Hudgins
Middle School Musical would’ve been a more entertaining alternative if everyone sang about food in their teeth.
15. Mark Ruffalo
I wouldn’t have minded my braces getting tangled with this guy’s, if you know what I mean.
14. Angelina Jolie
Comforting to know even the world’s most famous celebrity changed out her rubberband colors.
13. Fantasia Barrino
Accessorizing is key, which is great because braces match everything.
12. Gwen Stefani
This shit is bananas. But in all seriousness, be sure to brush your teeth after you eat bananas.
11. Marilyn Manson
I’m pretty sure Marcy Playground was inspired by these braces, no?
10. Blake Lively
OK we all know how this ends up, so there’s really no point in saying anything.
9. Faith Hill
Braces are exciting! Until they’re not exciting, you know?
8. Rashida Jones
I’m mildly convinced you can’t become a funny lady until you’ve gone through this exact stage of life.
7. Jeremy Piven
I don’t know which process was more painful: his overzealous plucking, the pinch from the puka shells, or adjusting his underbite. Probably the puka shell pinch, if I remember correctly.
6. Faye Dunaway
My mom had braces as an adult, so I know how you feel, Faye. Ain’t nothing gonna get in the way of you and your lipstick.
5. Drew Barrymore
At least we can all identify, am I right or am I right?
4. Elizabeth Hassleback
OK, so this is unfortunate. I’m not gonna sugarcoat it.
3. Gwyneth Paltrow
Like Gwyneth, I like the idea of kale and a nonjudgemental approach to life. With that said, this photo.
2. Ryan Seacrest
Cheese and rice, Ryan. I don’t even know what to say anymore.