Skateboarder Tony Hawk tweeted a photo of himself missing his front tooth, the result of crashing on his face. See photos of Jim Carrey, Demi Moore, Charlie Sheen, and other celebrities with imperfect grins. Clockwise from top right: AP Photo; Everett Collection; Twitter (2) Even legendary skateboarder Tony Hawk can’t land every trick. While performing this week at the Kona Skatepark in Jacksonville, Florida, the Birdman took flight and came crashing down—on his face. “Oops,” Hawk tweeted, sharing a snaggletooth photo, “doubles with Staab went wrong at Kona. Anyone know a good dentist in Savannah? <-- not a joke.” A day later, the 43-year-old Hawk was still smiling about the incident on Twitter “My new look,” he tweeted proudly. She’s posed naked and pregnant, so why not toothless? In May 2009, Demi Moore posted a photo of herself on Twitter as she was having some work dental work done on her famous smile. “Happy to share and always appreciate the opportunity to find humility!!!” she tweeted. “Or at least be able to laugh at myself!” As Moore later explained to Ellen DeGeneres, she “had a bad bite” and knocked her own tooth out. “Thank God for modern dentistry,” she said—with a perfected smile. In one of the funniest scenes of The Hangover, Ed Helms’ character, a dentist, wakes up and is horrified to discover he’s missing his front tooth. The gag wasn’t CGI, either. "It is totally real," Helms, explained to People magazine "I have an implant. An adult tooth never came in… and when I was 16, they did a permanent implant." But after some failed tests with prosthetics and blacking out the tooth, Helms opted for realism. "I wasn't eager to take out my implant because my mouth is healthy, but I talked to my dentist … and he was like, 'Yeah we can do it!' My dentist was really into it." Frank Masi / Warner Bros./ Everett Collection For a 2009 Halloween party, Paris Hilton showed up wearing a sexy Tooth Fairy costume. But two years earlier, Hilton could have used a visit from the real one. The hotel heiress was photographed in 2007 flashing a smile with a missing tooth. While Hilton never explained the mystery, misplacing things is apparently something of a pattern—during a recent visit to Manila, she lost two iPads. PacificCoastNews.com To make his Dumb & Dumber character, Lloyd Christmas, look even dumber-er, Jim Carrey removed a cap he’d had on his chipped front tooth since the third grade. ''Clark La Prairie jumped on my head in grade school detention,'' Carrey told Entertainment Weekly about the injury. ''The nuns sent me home with my tooth in an envelope.'' Carrey was particularly proud of his Method dentistry. “De Niro gains weight,” he said. “I file my teeth off.'' New Line Cinema / Everett Collection During Season 9 of American Idol, Crystal Bowersox endured snarky comments from Ryan Seacrest about her less-than-perfect smile, and politely declined the dental assistance producers offered all the contestants. “No thank you, New York dentist,” Bowersox wrote on the show’s official blog. “I am beautiful exactly the way I am.” But following the finale, Bowersox, the season’s runnerup, was all smiles on her Twitter account, posting photos of her new-and-improved teeth. "whats NOT missing in this picture??????” she tweeted. “Yeah. That's right." Andrew Weber / Zuma Grinning! Even when he was losing his number-one sitcom, Charlie Sheen smiled through the pain. With plenty of missing teeth. According to one of his former goddesses, Kacey Jordan, Sheen’s dental decline is a direct result of too much drug use. “All his teeth have fallen out from partying,” she told E! News. “He kept saying f---ing porcelain teeth... they crap. Said he had to get gold teeth.” And he is not shy about showing them. In February, TMZ showed photos of Sheen partying hard and flashing his bad gold grill. Ethan Miller / Getty Images When Amy Winehouse was photographed in 2007 flashing a goofy smile with a missing tooth, most assumed the dental decay was caused by her drug use. But the singer, who died in July at the age of 27, had a more mundane excuse for the gap: "My tooth got knocked out, that's true,” Winehouse told MTV.com. “I bit down on an ice cube and felt it come loose. I was sitting with my boyfriend and told him he had to pull it out because it was going to come out at some point and would be horrible and bloody. He wouldn't pull it out, so I had to do it myself.” PacificCcoastNews.com Having your teeth knocked out is an occupational hazard in boxing, but no gap-toothed fighter ever captured the public’s imagination quite like Leon Spinks. In 1978, the 25-year-old boxer shocked the world by defeating Muhammad Ali for the heavyweight championship, and the upset landed Spinks’ signature smile on the cover of Sports Illustrated. But Spinks admits that his grin has also made him a target. “They love my smile so much they steal my teeth,” he told the U.K.’s Observer in 2006. “Sometimes I leave them in the hotel. One time they were stolen by a maid or somebody who got a key to my room. People do some crazy stuff. I got mugged in Detroit once and I was trying to bite the guy and they came out and he stole them. It's so damn weird, people taking my teeth.” AP Photo A child losing a baby tooth isn’t exactly news, but it can be when you are the first-born daughter of Brangelina. In 2009, Shiloh Jolie-Pitt was photographed missing one of her front teeth, which immediately set off a debate about whether that was normal for a 3-year-old. E! online enlisted the expertise of pediatrician Jennifer Shu, who said, “I have never seen a kid lose a tooth as young as age 3 except for trauma or severe tooth decay—very, very severe." The Tooth Fairy could not be reached for comment. X17online.com