We found a great post about “less than perfect” smiles that made it big — really big.”

From the article by Thomas P. Connelly, D.D.S.

Here is a of “less than perfect teeth” list with many well-known actors, celebrities, and similar. In fact, for many of these people, you’ll see that their smile actually adds to their unique look, and in some cases, they may not have been as successful had they sported a “perfect smile.”

Steve Buscemi

Steve is our winner in the “least likely Hollywood smile” category. Discolored, crooked, protruding snaggletooth… Steve has it all. But think of the characters he’s played — Donnie in The Big Leboski, Carl in Fargo, Tony Blundetto in The Sopranos… seriously memorable characters that instantly come to mind. His characters come to life partly because of his unique look, and that includes his less than perfect teeth.

Jon Heder

Not much tooth makeup was needed to turn Heder into Napoleon Dynamite. But would he have been nearly as memorable with a perfect smile? No way, no how. Jon gets a lot of mileage out of his large choppers — they are actually the focal point of his face.

Gary Busey

Gary has really large teeth that go straight across – they are sooo straight across it almost looks like they are artificially made to be that way (but they aren’t — who would do that?) Gary’s teeth definitely lead to his characters jumping off the screen — when he smiles, you really can’t tell if it’s warm or sinister… Gary keeps you guessing. A great asset to a great actor.

Mike Tyson

The “Baddest Man on the Planet” had a smile that could make grown men shiver. Exemplified by the “gold grillz,” Tyson’s smile is a mix of missing teeth, jagged “out of place” teeth, and more. But you know, it also has a warm quality to it. I couldn’t imagine “Iron Mike” with a Hollywood smile.

David Letterman

Is there a more famous “gap” than David Letterman’s? It’s unlikely — his gap is a definite part of “him” that it’s hard to imagine Dave without it. Every caricature of Dave emphasizes his famous gap, and it’s not done with a hint of meanness — it’s just Dave.

Madonna

Let’s not make this a “guys only” list, ok? Madonna is entering her third decade as a major pop star, sex symbol, and whatever else she chooses to be. In fact, it’s arguable that there hasn’t been a more influential female star in the last twenty years. And she’s done this with a smile that’s part Letterman, part Busey, and all Material Girl. She’s hot, she’s happening, she’s got a less than perfect smile, and she doesn’t care. She’s Madonna, and that’s that.