Steve Buscemi smiling

The following article includes mentions of drug and alcohol addiction.

Crooked, misaligned, yellow, and gapped. These are just a few of the words used to describe some of the worst teeth in showbiz. In an industry that’s fixated on perfection, so-called bad teeth are a radical battle cry against impossible beauty standards. They beg the question: Isn’t how I am good enough? The answer is a resounding yes (even if your Whitestrips can’t keep up with your coffee habit).

Hollywood loves a good tooth transformation, but these A-listers aren’t biting — literally. Some of the stars on this list have been boldly flashing their imperfect smiles since the start of their careers, shaking off criticism like a piece of kale stuck between the gap in their front teeth. They’ve managed to transform their flaws into a bona-fide signature look that’s celebrated and respected. When a whole generation is suffering from Face Tune-induced Instagram face, a few snaggle teeth aren’t anything short of refreshing.

Despite the Hollywood faux pas, these celebrities smile through the criticism — crooked teeth and all.

Lindsay Lohan’s teeth were ‘chipped and discolored’

Lindsay Lohan smiling

Lindsay Lohan shocked fans when she debuted a new look in 2011. No, it wasn’t the natural redhead’s blonde dye job that threw people into a tizzy. It was the appearance of her teeth that made the world shudder.

The Sun described her smile as "seriously chipped and discolored," and some attributed her gnarly grin to her hard-partying and drug use. It was very difficult to see the former child star in such a state, but Lohan seems to have cleaned up her smile, even if the rest of her lifestyle remains up for debate.

By February 2018, the mucked up teeth she was previously sporting appeared to be long gone. She flashed a set of pearly whites in a short video for W magazine. In the clip, Lohan recites some of the now infamous lines from her 2004 hit film "Mean Girls" — you know, for nostalgia purposes — but we’re pretty sure what she really wanted to tell the world was: "New teeth, who dis?"

If you or anyone you know is struggling with addiction issues, help is available. Visit the Substance Abuse and Mental Health Services Administration website or contact SAMHSA’s National Helpline at 1-800-662-HELP (4357).

Johnny Depp’s mysterious red tooth

Johnny Depp smiling

We wouldn’t necessarily coin Johnny Depp’s career as a "fall from grace," but some say the "Pirates of the Caribbean" star has gone from heartthrob to hot mess in the blink of an eye. He was involved in a widely-publicized 2017 divorce with actor Amber Heard, and it was during their rocky marriage when his appearance — particularly, his teeth — took an unexpected turn.

In 2015, when Depp attended the screening of the film "Black Mass" with his then-wife, many were taken aback when he parted his lips, revealing dental work similar to the gold caps he wore while playing pirate Jack Sparrow, plus a mysterious red tinge on one tooth. You can almost see the foul breath creeping out of Depp’s rainbow chompers.

Depp’s bridgework might make you cringe, but Hollywood is still knocking down his door. After all, a shoddy grin is nothing that an experienced prop department can’t tackle. Depp was apparently fitted for a pair of fake teeth for his 2017 role in the film "Murder on the Orient Express."

Don’t ask Anna Paquin about her gap

Anna Paquin smiling

Anna Paquin became the talk of the town when she was cast as Sookie Stackhouse in the HBO vampire series "True Blood," and though vampires and teeth go hand in hand, the actor attracted a lot of attention for the space between her front teeth.

In an interview with Zooey (via Just Jared), Paquin said her gap-toothed grin is the furthest thing from her mind. "Interestingly enough, I don’t really care about my teeth," she explained, "but I think any woman on this planet could say, ‘I wish my a** was smaller, my arms were thinner and I had green eyes not brown.’ I think anyone is as critical as they have the energy to self-obsess, but I also know as an actress you are more limited if you interfere with your looks."

Paquin has no intention of altering her natural smile. In fact, she told Us Weekly (via The Hollywood Reporter), "I find it rude when someone asks me why I never ‘fixed’ the gap in my teeth!"

Vanessa Paradis is a human water fountain

Vanessa Paradis smiling

French girl beauty has a certain je sais quoi that’s become ever-popular in the mainstream. It’s so ubiquitous that Vogue unpacked the nuances in a 2021 article. All in all, it can be defined by just one trait: an effortless cool.

Multifaceted French star Vanessa Paradis is the epitome of French girl beauty — and that includes the gap between her front teeth. As the French say, Paradis has les dents du bonheur, or teeth of happiness. They’re meant to bring good fortune if you happen to be superstitious. In other words, those teeth may have helped her score four Top 10 hits on the Billboard charts. Needless to say, the singer has no desire to mimic the cookie-cutter smiles of her showbiz peers.

"Why would I fix them? I was born with them," she told Harper’s Bazaar in 2012. "I can spit water through them. They’re useful." You heard it: Paradis’ not just an international star (wrapped up in some unfortunate drama with ex Johnny Depp), she’s a veritable water fountain, so long as you have a bottle of Perrier on hand.

Madonna is ‘grillin’ to tick everyone off

Madonna with teeth grill

Pop icon Madonna has always played by her own set of rules, flashing an attitude that is equal parts blasé, lovable, and deviant — with the smile to match.

The "Material Girl" hitmaker and her gold teeth became a hot topic of discussion in 2014. She told Ryan Seacrest (via News.com.au): "Yeah, I’m grillin’. … It p****s everybody off when I wear my grill, so that’s why I wear it." She also revealed she only accessorizes with her tooth bling when it matches her outfit, and that she "learned to eat" while wearing the dental apparatus, too.

We suspect it’s a pain to clean out all the gunk that piles up inside the dips and grooves of a grill after a hearty meal, but at this stage of her career, Madge certainly has enough funds to hire someone to keep her mouth gear sparkly.

Anthony Davis’ teeth commit a technical foul

Anthony Davis laughing

Many folks are perplexed by Los Angeles Laker Anthony Davis’ headline-making unibrow — another so-called flaw the NBA star refused to fix. "It just makes me different," he told ESPN in 2012. That’s not the only aesthetic foul he’s committing on and off the basketball court. The baller’s bottom teeth have stirred up a lot of (admittedly superficial) hoopla, even from dentists. Some critics went as far as saying Davis had the "worst teeth" ever in the NBA.

If you look closely at photos, it’s not hard to see that Davis’ bottom teeth are very misaligned. That’s not a problem on the court, but according to Healthline, crooked teeth can cause TMD and chronic headaches. Nonetheless, Davis still won a gold medal at the 2012 Olympic Games. Back when he was on the New Orleans Pelicans in 2015, he took his team to the NBA playoffs. He was even dubbed the All-Star MVP in 2017. It’s almost as if crooked teeth have no impact on your ability to play basketball. Let’s remember, Davis is a world-class athlete, not a tooth model.

Charlie Sheen ‘doesn’t care’ if you hate his gold teeth

Charlie Sheen smiling

In 2012, while he was still playing the role of Charlie Harper on "Two and a Half Men," Charlie Sheen told ABC’s "Nightline" that he rocked some gold jewelry during his downtime. The jewelry wasn’t in the form of a necklace or a bracelet, though. It was actually located in his mouth.

According to Sheen, he had a gold tooth put in back in 2010, but he made sure to have it covered up while filming the hit TV show. Why hide it? "I don’t care. It’s the other people that have the problem with it," he said.

But according to tabloids, the actor’s gold dentistry wasn’t just a flashy accessory. It was allegedly used to cover up the damage that had been done after years of alcohol and drug abuse. According to The Sun, one of Sheen’s former lovers claimed his original teeth had "fallen out from partying," and TMZ lent some credence to that hearsay with this footage.

If you or anyone you know is struggling with addiction issues, help is available. Visit the Substance Abuse and Mental Health Services Administration website or contact SAMHSA’s National Helpline at 1-800-662-HELP (4357).

Steve Buscemi is afraid he ‘won’t work again’ if he fixes his teeth

Steve Buscemi laughing

Actor and director Steve Buscemi is really giving the middle finger to the industry. Not only has he embraced the somewhat tired and wrinkled appearance of his eyes (which later turned into a meme and a blog called "Chicks with Steve Buscemeyes"), he also has a mouthful of misaligned teeth. He’s practically the antithesis of a Hollywood leading man, but does that mean he’ll be running out to Botox his eye area or undergo costly dental work? Not a chance!

In an interview with The Hollywood Reporter, the Emmy Award-winning actor said, "I’ve had dentists who have wanted to help me out, but I say, ‘You know, I won’t work again if you fix my teeth.’"

His ill-favored teeth are quite endearing, and besides, who does the "Reservoir Dogs" actor really need to impress anyway? He’d been happily married to the same woman, wife Jo Andres, for over three decades until her tragic death in 2019.

Tom Cruise’s ‘monotooth’ can’t be unseen

Tom Cruise smiling

At first glance, Tom Cruise’s teeth appear to be in pristine condition, but upon further inspection, the "Jerry Maguire" star dons what The Sun has dubbed a "monotooth." You don’t see it? Look a bit closer. One of his top teeth is a bit off-center, shifting it to line up smack dab in the middle of his mouth. According to the publication, the shift in his top row of teeth was due to "so much dental surgery." So, what’s the real deal?

Let’s be honest. Tom Cruise is hardly the first person to have a misaligned front tooth, which many have dubbed his "middle tooth." Nonetheless, Life & Style did a deep dive into the star’s unique chompers. Per the tabloid, the monotooth was chipped by a hockey puck and covered with a cap — which Cruise actually took out for his role in the 1983 movie "The Outsiders."

The story of Cruise’s teeth doesn’t stop there. In the early aughts, following his dramatic divorce from Nicole Kidman, the star got braces. You can see them in old red-carpet photos from 2002. That didn’t seem to fix the so-called monotooth, and some dentists speculate the star has veneers. Either way, all these years later, the media is still swooning over Cruise’s smile.

Michael Strahan has embraced his gap, and you should, too

Michael Strahan smiling next to bust of himself

There are three things Michael Strahan is known for: his 15-year NFL career with the New York Giants; the drama that ensued following his departure from "Live! With Kelly and Michael;" and his charming, gap-toothed smile.

In a 2012 interview with Elle magazine, Strahan revealed he wasn’t always in love with the divide in his grin: "I was really close to closing [the gap] up. I was at the dentist having him do mock-ups. I thought about it, man." The incident happened when he was still playing professional football, and even as an athlete, he said he felt "so much pressure to be perfect." In the end, the Super Bowl champ decided to embrace his gap, partially because he didn’t want to alarm his four children. "For me, I made the conscious effort to say ‘This is who I am.’ I’m not perfect. I don’t want to try to be perfect. At this point, I don’t think my kids would recognize me without it. They’d be like, ‘Who is this stranger in the house? Call 911!’"

Long live the gap!

Keira Knightley isn’t pressured to change her ‘wonky’ teeth

Keira Knightley laughing

Keira Knightley has self-proclaimed "wonky" teeth — and at the height of her fame, the media wouldn’t let her forget it. At a 2018 "BAFTA, A Life In Pictures" event (via Yahoo! News), the British star got real about how the success of "Pirates of the Caribbean" opened up a world of criticism about her appearance. "You have, ‘Her face is beautiful,’ and then you have, ‘Her face is disgusting and her mouth looks like a bangle,’" she said. "Everything was really extreme."

Despite this, Knightley never felt pressure to change (aside from the using the odd foot double on-set, but that’s another story). As she told CBS News, "I keep hearing about everybody going to Hollywood and, you know, their agents going, ‘Straighten your teeth,’ or, ‘Whiten your teeth,’ but nobody’s ever said anything about my teeth. They’re not straight, apparently. But nobody’s ever said anything, which is quite nice I suppose."

Today, Knightley’s crooked smile is (rightly) celebrated in the mainstream press. As Vogue put it, the actor’s "dewy English rose complexion and symmetrical features would be flawless to a fault without her slightly misaligned tomboy canine." We couldn’t agree more. Plus, who else can play their teeth like a musical instrument?

Katy Perry’s teeth are the ‘bane’ of her ‘existence’

Katy Perry speaking

Katy Perry has picked up a side gig as an "American Idol" judge, and there’s one thing she’s judging about herself — her crooked teeth. In an interview with InStyle (via the Daily Mail), the star proclaimed, "Those teeth are the bane of my beauty existence. It’s like the Rocky Mountains in there!" So, why doesn’t she fix them like other celebs? She knows adult braces — and years of a retainer that likely follow — are no walk in the park. "It’s hard as an adult to commit to them," Perry said.

In the past, the "I Kissed a Girl" singer has digitally altered her videos to straighten her teeth, but she’s started embracing her natural beauty in more recent years. In 2019, Perry left her real smile intact in the music video for "Never Really Over." When fans took notice, the star admitted on Twitter that she was "tryin’ harder every day to accept myself." Self-acceptance is a long process, even for someone with 13 Grammy nominations.

Jewel’s crooked teeth made her a movie star

Jewel smiling

Jewel’s path to fame wasn’t easy. The star had a traumatic childhood and ran away from home at the age of 15. She was one of the few celebrities to navigate homelessness before fame. Of course, everything changed when she got her big break with 1998’s "Who Will Save Your Soul" — everything except her teeth. Her imperfect smile has become her trademark. "People have always loved my snaggletooth, which is hilarious," Jewel told Health (via Yahoo! Entertainment) in a 2013 interview. "It should be my logo! I’ve never felt like it didn’t make me sexy."

Much to the dismay of the Hollywood agents who pressured her to fix her smile, Jewel’s crooked teeth have actually become an asset. In 2010, she told Shape (via Yahoo! Entertainment) that she landed a part in "Ride With the Devil," a 1999 Civil War film, because the director thought she had "period teeth." "I got the job because I was the only actress in Hollywood who hadn’t gotten her teeth fixed," she said.

That’s not to say Jewel never did any dental work. According to the Daily Mail, she did put a porcelain veneer on "one of the more crooked of [her] teeth" in 2009, but she’s largely kept the same smile. The only time it drastically changed was when she wore prosthetics to play June Carter Cash in Lifetime’s "The June Carter Cash Story."

Hilary Duff’s teeth can’t catch a break

Hilary Duff's smiling

Hilary Duff can’t catch a break with her teeth — or rather, she catches too many breaks. Though the "How I Met Your Father" star’s smile looks perfect today, she’s dealt with numerous broken teeth. As iHeartRadio points out, Duff regularly chipped her teeth on microphones back in the Disney days. There are still a few photos from the era floating around that showcase the damage. Eventually, she reportedly replaced her teeth with veneers. The veneers, however, betrayed her.

Nobody wants to have emergency dental work on their wedding day, but Duff had no other choice when she married her first husband, hockey player Mike Comrie. In an interview with Ellen DeGeneres, the former Disney Channel star revealed that three hours before she was supposed to start getting ready to walk down the aisle, she "bit into a bagel" and her "tooth fell out" into her hand. "Thank God I didn’t swallow it," she said. Her wedding planner was able to pull some strings and find a dentist, so Duff was spared the toothless wedding photos.

At the end of the day, the whole thing seemed like bad luck, but in retrospect, it could’ve been a bad omen. Duff divorced Comrie in 2016, essentially telling The Talk (via People) that she was "too young" to tie knot. Nonetheless, she claims to have no regrets, and now has a super sweet marriage to record producer Matthew Koma.