While celebs and their entourages often take up blocks of expensive suites, sometimes they are just not worth the hassle or bad publicity.
Police say they found Sheen, 45, drunk and naked in a trashed suite at the Plaza earlier this week. Sheen's representative said the actor was not drunk, but suffering from a severe allergic reaction.
Sheen's ex-wife actress Denise Richards and their two daughters Sam, 6, and Lola, 5, were reportedly staying across the hall at the hotel's Eloise Suite.
The hotel spent a small fortune renovating the two-room suite on the 18th floor that rents out for $995-a-night. The room is fashioned after the hotel's most famous "resident," Eloise, the irreverent and irrepressible fictional heroine of Kay Thompson's classic book and has been heavily marketed by The Plaza.
"Now every time that somebody stays at the Eloise Suite, they are going think this is where Charlie Sheen was," with a porn star said Rob Shuter, the Naughty But Nice columnist on PopEater.com. "It's not the image The Plaza wants. Overnight, Charlie has just undone a multi-million image campaign."
Shuter said Sheen's alleged actions are exactly why a some hotels don't want stars as guests.
"They don't want the paparazzi outside, they don't want the entourage walking through the halls at 2 a.m.," he said. "A lot of hotels pass on the big stars."
The Plaza has not commented on the incident except to say that Sheen himself was not staying in the Eloise Suite.
With Sheen in mind, ABCNews.com took a look at some of the worst celebrity hotel room destructions of all time.
Worst Celebrity Hotel Guests
Probably the best-known hotel-smashing stars were the Rolling Stones -- although they are said to have calmed down in their elder years. Still, hotels expect the Rolling Stones to trash a room. That's part of their rock star image.
"I assume before they arrive, the hotel knows to remove anything valuable," Shuter said.
Other celebrities require other preemptive measures. For instance, Shuter said, whenever Madonna travels she insists that all the furniture be taken out of an adjoining room so she can work out.
But the bad behavior is not limited to rock stars. In June 2005, Academy Award-winning actor Russell Crowe threw a phone at the concierge at New York's Mercer Hotel. Crowe, who later pleaded guilty to charges, was apparently angry because he couldn't call home to Australia. There were also rumors of a multi-million dollar settlement paid to the concierge.
"These hotels are very discrete places," Shuter said. "A lot of their guests are very private businesspeople who are there to work. They don't want to bring clients back to the hotel for drinks and have to navigate a line of paparazzi."
Britney Spears isn't too welcome at the Standard Hotel -- Downtown LA after an August 2007 incident in which she reportedly got naked at 2 a.m. in the hotel's pool and tried to seduce a college boy. Other members of her entourage apparently joined in the late-night pool party.
Then there was the incident in June 2006 where Guns N' Roses star Axl Rose was accused of biting a hotel security guard's leg and smashing a mirror at the Berns Hotel in Stockholm, Sweden. He eventually pleaded guilty to related charges.
Finally, it might seem unlikely now, but now-reformed actor Johnny Depp was as big of a bad boy as anyone in his younger days. In September 1994, police arrested Depp and his guest, then-girlfriend Kate Moss, in the presidential suite of New York's Mark Hotel after the couple apparently made too much noise and damaged the room. Depp was reportedly arrested on charges of criminal mischief, but the charges were dismissed after he paid thousands in damages and fees. The actor later said he was just trying to crush a cockroach and the furniture got in the way.
"It just goes to show that young people can really change," Shuter said. "In their youth a lot of actors and rock stars were immature."
Shuter said Depp grew up really admiring Rolling Stones bad boy Keith Richards.
"The new generation of stars have grown up with a very different roadmap," he added. "I predict we will see less and less of this."
Celebrities and Their Bad Behavior
Despite the long history of meltdowns, for Shuter, Sheen's latest incident wins the prize for worst celebrity hotel room destruction.
"There's lots of stories about rockers or rock band acting bad in hotel rooms, but this is really hard to top; his ex-wife and daughters were sleeping across the hall," he said. "He didn't just trash the room but ended up in the hospital. That's a pretty high bar to beat."