Worst Celebrity Smiles – Why We Grimace at Their Grins

By Lauren Triolo

Published on May 09, 2008

Whether their claim to fame is starring in a hit Disney television show, earning five Grammy® Awards in one night, or marrying the lead singer of Sum 41, the following celebrities share common ground – they are rich and talented and attract attention wherever they go. Though it would seem that everyone on our list has plenty of reasons to smile, one could argue that there are 32 reasons why they shouldn't! While these celebrities laugh and smile all the way to the bank, most of us would prefer they kept their mouths shut altogether. A chip here, a crack there, super-sized gums, and other major mouth misfortunes have landed each of the following stars a spot on our "Worst Celebrity Smiles" list.

Note: We certainly have not graduated from dental school or been professionally trained in the field; however, we would like to offer these stars some friendly suggestions for cosmetic dentistry procedures we think they should check out.

#10) Kirsten Dunst

Kirsten has graced the silver screen with performances in Interview with the Vampire, The Virgin Suicides, and the Spider-Man movies. However, with her thin lips and crooked, yellow teeth, she sure doesn't have a “Mona Lisa Smile.”

Suggested dental treatments: crowns, veneers, and a whitening treatment

#9) Condoleezza Rice

Some may argue that the secretary of state has more important things to worry about than cosmetic teeth bonding, but let's not ignore the obvious. And though she may have been concerned with securing the borders when she served in President Bush's cabinet as national security advisor, she was hardly concerned with securing her own mouth. Condi's gaps are big enough to hide foreign objects in... Osama Bin Laden, perhaps.

Suggested dental treatments: veneers and crowns to clean up her front teeth

#8) Avril Lavigne

Avril has enough working against her with her beady eyes and pointy nose. A glance at her fang-like incisors only makes her appearance more “complicated.” I thought she was from Canada, not Transylvania!

Suggested dental treatments: Invisalign® and a couple of properly-shaped veneers on those blood-sucking chops

#7) Steve Buscemi

Steve has made a successful television and movie career out of playing the strange and awkward sidekick. I’d wager a bet that the real reason Steve’s character got whacked on The Sopranos was his completely offensive smile. Also, rumor has it that his stained, jagged smile convinced the producers of Charlotte’s Web to cast him as the voice of Templeton the rat.

Suggested dental treatments: porcelain veneers to correct the shape and color of his teeth

#6) Jewel

We love Jewel for her songs, poetry, and humble living-in-the-back-of-a-Volkswagen-van roots. She also looks like your typical girl next door - until she smiles. Then she looks like your typical girl next door who tried to open a Jones Soda bottle with her teeth and failed miserably. Never mind who will save your soul – who will save her smile?

Suggested dental treatments: Invisalign® and teeth whitening

#5) Anna Paquin

This dark-haired beauty has had roles in such cinematic masterpieces as The Piano, Amistad, and the X-Men trilogy. Her film career blossomed early, and she earned an Oscar® at the age of 11 for her role in The Piano. A little known fact is that she is listed in the film’s credits as both actress and prop master - they used her teeth to fill in any missing piano keys.

Suggested dental treatments: veneers to fill in the gap and shorten her two front teeth, plus a tooth whitening treatment

#4) Jon Heder

Luckily, Jon is better known for his killer sense of humor in movies like Napoleon Dynamite and Blades of Glory than a mega-watt smile and dashing good looks. If I were him, though, I’d spend less time voting for Pedro and more time in the dentist’s chair fixing those horrific buck teeth.

Suggested dental treatments: a complete smile makeover, including braces to reshape his jaw and correct his overbite, veneers, and possibly some gum recontouring

#3) Melinda Doolittle

One of our favorite super-talented “American Idol” alums is apparently still waiting for her baby teeth to fall out. Until they do, Melinda's gums will continue to take over her mouth with the size and proportion comparable to a player in “Hungry, Hungry Hippos” going after white marbles!

Suggested dental treatments: gum recontouring and porcelain veneers (she can skip the Rembrandt® whitening treatment; her natural tooth shade is gleaming!)

#2) Flavor Flav

Much like his lady lovers on the TV show Flavor of Love, it’s obvious that Flav prefers his teeth flashy, trashy, and loud. The former Public Enemy and VH1 reality star credits himself with popularizing the “grill” trend, a trend that not only looks ridiculous, but brings up questions of hygiene as well – does he use jewelry cleaner instead of toothpaste?

Suggested dental treatments: ditch the gold grillz and slap some natural-looking porcelain veneers on those bad boys… unless the gold teeth are covering up a normal set of pearly whites

#1) Amy Winehouse

Amy Winehouse was one of the biggest stars of 2007. Her sultry, soulful voice earned her loads of critical acclaim, money, and adoration. However, as much as her admirers look up to her, it’s quite hard to look at her without wincing. This Grammy®-winner has a bigger Gap than the Mall of America.

Suggested dental treatments: a dental implant, a few veneers, and a teeth whitening treatment