Hilary Duff has a pretty smile

February 10th, 2006 // 109 Comments

Hilary Duff, by Hollywood standards, seems fairly normal. She looks like the sort of girl who’d marry the star pitcher in high school, have three kids, and settle down into obscurity. But her teeth. You could screen a movie on those things. An IMAX movie. A word of advice for future boyfriends – they don’t call her “the scraper” because she cleans ice off your car in the morning.

UPDATE: This may be Haylie Duff. But my big teeth argument holds.


  1. Lynette Carrington

    Well, whichever Duff this is, she sure looks a helluva lot like Kylie Minogue.

  2. LaydeeBug

    #44, HollyJ, thanks for the belly laugh, you are a fucking genius.

    #48, OH MY GOD, hahahahahahahha, I love Wanda. (Oh Kayyyyyyy?)

    O lawdy, this is fun!

  3. gsprescueguy

    It makes you wonder if this girl has a mother and father. Not only is she wasting away losing weight, but she decided to spend $20K+ on having surfboards glued to her teeth.

    She could probably drop half her body weight having them removed.

  4. DuckBoy

    That is DEF Hillary….Hayley Duff has a HUGE mishapen nose

  5. LaydeeBug

    Yep, that’s Hilary all right. Hayley may look like her but Hil is the “ahem” prettier one. (Though they are both pretty cute)

  6. normella

    meeehehehee ::gallops away::

  7. Krissy

    she had to have them replaced when she chiiped them on a microphone…but i would think that she could have chosen some that fit her face and mouth

  8. SoulxRebel78

    She should probably learn not to eat the microphone, rather than having gotten veneers. If she really is chipping her teeth singing, then she’s gonna end up chipping the veneers too.

    LMFAO #56!

  9. Mr. Fritz

    Let’s be totally honest, she has been shrinking in size like every young actress. She had to get new choppers because the acid from her vomit destroyed her teeth.

  10. I like the new Superficial format:

    [celebrity] [verb] [something else]

    and then a huge nasty picture that totally contradicts the title. It feels a little canned, but that doesn’t mean it’s any less funny everytime.
    H. Duff would be pretty if she would just shut her damned mouth; I like the Kylie Minogue look on her.

  11. Brokeneyes

    That is definitely hillary. I’ve always hated her. She should just go back to acting on pointless disney shows. That way the majority of America can stop looking at Mr. Ed in technicolor…except if you are Americans with kids that happen to like the Disnry Channel…then you are just screwed.

  12. LaydeeBug

    #56, yer killin me. The girl in the other cubicle must think I’m a nut.

  13. Sara

    Yeah… that picture is photoshopped.

    But she does have some damn big teeth, besides that.

  14. julema

    haylie have a much BIGGER nose!
    I don,t care about her teeth!
    I think she’s cute… i prefer hilary compare to young slut like Lindsay…Hilary dress right, she never got implants ( her boobs are small and she didn’t get them bigger!!) she never used collagen, she have a long time boyfriend, don’t change boyfriend like changing her slips! Don’t spend her time partying…well i respect her and i don’t respect Lindsay. Hilary is a good role model for young girls!

  15. HughJorganthethird

    Does anyone remember the cartoon from the 70′s featuring The Toothbrush Family? Well when they saw Hilary they all jumped into the toilet and commited suicide.

    Someone get that thing a salt-lick.

  16. LH

    Just pay another Grand-a-tooth and file those bad boys down a little, and while your at it, go back to blonde so we know which one you are….

  17. Cosmopolitan

    Yeah, Hilary for sure. Haylie has that horrible witch nose, and extremely pointy chin.

  18. dimestoredetective

    I’d hit it.
    A little Lizzie McGuire lovin’.
    She’s 19 right?
    Sometimes I have dreams of a Duff-Lohan-Olsen Twins-Jessica Simpson pillow fight. I need to go now.

  19. Layne

    i thought hilarys eyes were blue??

  20. eskimospoon

    I did a google images search and they both have brown eyes, damn sisters.

  21. beeotch1031

    it cant possibly be haylie… know why? elephants arent lining up to do the nasty… however, i hear beavers are clearly impressed by the new hilary. they would definitely hit it.

  22. LoneWolf

    Hilary’s metamorphis-izing into Sea Biscuit. My schvantz would retract like a frightened turtle if its one-eye saw those chompers coming in its direction.

  23. suzy

    yes her teeth are fucking huge, maybe next time she could fix her huge ass forehead!!

  24. redleigh

    I find it funny that hardly any of you can tell the difference between Haylie and Hilary.

    Ones very ugly (Haylie – #67 puts it best) and the other is normal (Hilary – THIS ONE).

    I promise you that IS Hilary. Besides, Haylie’s teeth aren’t as big.

  25. IH8Neve

    That’s Hilary, because she obviously doesn’t have Haylie’s schnoz.

  26. suzy

    here’s a picture of them together…



  27. keepitrealchick

    it is artificial, but i think it looks hot!

  28. keepitrealchick

    i think she is totally hot!

  29. Frankly, I think she’s lovely and the new, more natural hair
    color adds a lot of class to the overall package. She is a
    better role model than most of the other Teen Queens!

  30. jennyjenjen

    Her teeth are to big, but they give her a sophisticated lookl she didn’t have before. I dunno, I kinda like her. Boring post.. sorry.

  31. jonathanwithaj

    You know, before this picture I liked her but that was of course before I knew she had her ears double pierced. DOUBLE PIERCED!!! What are you a Tai hooker now Hilary? Geez, what’s next big teeth?

    Oh, well nevermind you Asian whore.

  32. clitcommander

    You would think she might have wanted to think this through a little bit more before going all Mr. Ed on us.

    I mean, how the hell is she going to get her fingers in her mouth to throw up the 2 triscuits she ate this morning with all those damn teeth in the way?

    I’m just sayin….

  33. Charlie

    I don’t why tiny people get veneers, they really enlarge the mouth and whoever her dentist was should be sued big time….she had a lovely smile before this…..now she looks like a pony.

  34. senin

    Christ, she looks like Mr. Ed! Her dentist should be drawn and quartered.

  35. nichole

    She said somewhere that she had to get veneers b/c of some condition where she was always chipping her tooth, but couldn’t she have gotten a regular size???


    Caption: “Duuuuuurrrrrr”

  36. ir0ny!

    Hillary has nice eyes, but in general she’s on the verge of the “anorexic” thin look, which actually makes her less attractive. Which then also makes her teeth even more noticeable cuz her chin also protrudes. So it’s more like, her face tried to pack a lot of “big” features in, into as little space as possible. Probably putting on just a little weight will help her look better, but right now she looks like a balloon on a string.

  37. biggutonenut

    Id hit it faster and harder than babe ruth taking down a fastball.Period.

  38. pixie-stix

    She really needs to not do the toothy smile. I keep thinking she’s gonna whinny.

  39. ESQ

    Imagine what her boyfriend must go through. I think she is waiting for an opening at the dentist to file them down. Or at least should.

  40. boogerman

    elephants would be jealous of all that ivory!

  41. susie-q


    This pic takes the cake. I’m sure there is not a day that goes by that she is not kicking herself for getting totally screwed on that dental job.

    With all the $ she must have, I don’t see why she hasn’t had them redone. Can she honestly be happy with them? Wouldn’t surprize me one bit.

    Plastic surgery and new front teeth and things of that nature scare me. It’s your face for God’s sake. Especially with noses – there’s only so many times you can try to correct a bad nose job before you end up scarred for life.

    Anna Nicole Smith had the same dilemma with her new teeth. They are almost as bad as Hilary’s. They should both try to have them reduced or redone. Or something. Hideous.

  42. Bales

    #74 – I also find it quite funny that people have such a hard time telling Hilary and Haley apart. Their facial differences are glaringly obvious. And it’s actually fairly common for singers to eff their teeth up on the microphone. Her new teeth are out of proportion to the rest of her features, but she’s still beautiful; and she seems to be a very loyal person who is ambitious and diligent. That’s a lot more than you can say about the majority of girls her age. Hell, that’s more than you can say about most people of any age. Give her an effin break.

  43. Celetina

    Bales: if that girl is a singer than I’m the pope. The zombie pope. Singers who “eff up” their teeth on the microphone are not singers so much as desperately confused whores assuming that any long, cylindrical object needs to be crammed into their mouths.

    You should’ve seen what happened to her at her sister’s last birthday party. It’s the first time in California state history that the paramedics were called for somebody trying to deep-throat a lit candle.

  44. Richard

    Big teeth or not … that woman is absolutely beautiful. Look at her eyes, nose, lips, cheekbones and over all facial structure. Her symmetry is perfect and her skin is flawless.

    I’d bang the hell out of her.

  45. becca11

    lol, woman?

  46. FuzzyFace

    Hilary Duff USED to be pretty but has fallen for the Hollywood myth that “skinny” is the way to be. Before she was an all-american girl, now she’s undernurished and looks scary. It could also be due to extraneous factors (ahem…Lidsey Lohan’s problem). I wish she would gain 20 pounds and be the sweetie that she was.

  47. Celebrity Crunch

    Anyone dating Hilary Duff is seriously going to need one of these t-shirts: http://www.cafepress.com/macycreative/1164494

  48. bakismaki

    They should have hosted the winter olympics on those huge snow caps hilary duff calls teeth.

  49. Willlllllllbur! Get me a carrot, Willllllbur. “A horse is a horse of course of course…’

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