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“You’re never fully dressed without a smile!” cheers the eponymous song from Broadway’s Annie, and pop culture is certainly filled with memorable characters who just can’t stop cheesin’. Some smiles are broad, others quiet and mischievous. Some smilers are clever tricksters and others are insecure middle schoolers, but regardless of style, we’re rounding up all of the most memorable mandibles in pop culture!

 

Mona Lisa, Leonardo DaVinci

The Mona Lisa is perhaps one of the most well known and beloved portraits ever created, and the most entrancing thing about her is the subtle smile she wears. Historians, novelists, conspiracy theorists, and art lovers alike have all speculated on what the significance of her quirked smile, though the truth may remain forever a mystery. Either way, no one can talk about memorable smiles without thinking of this classic masterpiece.

 

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Cheshire Cat, Alice’s Adventures in Wonderland

If there ever were a grin that exemplified kookiness and smugness in one sinister smile, it would be the toothy smirk of the Cheshire Cat from Alice’s Adventures in Wonderland.  “We’re all mad here,” is his teasing refrain as he teleports from branch to branch, offering so-called wisdom, all the while confusing poor Alice more and more.

 

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The Grinch, How the Grinch Stole Christmas

The Grinch’s malevolent, Christmas-stealing-smile is perhaps one of the most GIFed images on the internet. It’s slow and sinister upward curl is iconic in the truest sense of the word. The only thing more impressive than this animated heart-freezing grin is the fact that Jim Carey, who played the Grinch in the live action version released in 2000, can actually make the face in real life!

 

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The Joker, Batman

“Let’s put a smile on that face!” cackles the Joker in almost every adaptation of the classic character, another example of a crazed smiler. The nefarious clown has more backstories for his smile than he does teeth, but the ambiguity of his smile doesn’t make it any less terrifying. Whether he’s frustrating and bamboozling Batman in the movies or on the page, this comic criminal is one of our favorites.

 

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Pac-Man

If you’ve ever played an arcade game in your life (and even if you haven’t) you’ve probably seen the incredible chomping jaws of Pac-Man racing towards a blue and white ghost, or perhaps a juicy bonus fruit. When you’ve got a smile that takes up half your face, you’d want to show it off too! Pac-Man has been grinning and gaming since the 1980’s and is still going strong with more than thirty licensed game appearances to his name.

 

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Stanley Ipkiss, The Mask

Stanley Ipkiss is the average-Joe banker who stumbles across a supernatural mask that grants its wearers superpowers in The Mask series of comics and movies. The mask in question gives its wearer not just superpowers, but also an enduring smile that leers at the viewer, no matter the tone of the scene. This is also another nod the incredible facial muscles of Jim Carey, as he played the hapless-turned-hokey Ipkiss in the 1994 film adaptation.

 

Raina Telgemeier, Smile

Not everyone has a perfect smile… especially in middle school! Adolescence can be one of the hardest times to find a reason to smile, especially when your front two teeth are accidentally knocked out! Luckily, Raina Telgemeier’s award-winning graphic memoir Smile exists to help kids going through their own dental woes love their smiles too.

 

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Toothless, How to Train Your Dragon

Nothing is cuter than Toothless from the How to Train Your Dragon movies. His smile is a little different from most of the others on this list, because instead of a mouthful of shiny choppers, he’s as gummy as his name suggests. But don’t let his adorable smile fool you – mess with him too much and his fangs will come out!

 

Which smile is your favorite? Tweet us at @quirkbooks to let us know!


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Hannah Frank

Hannah Frank is a creative writer, television aficionado, and cool ranch Doritos fan. She wishes she could live forever and is currently seeking advice on how to do so which does not include exercise, kale, or vampires.