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.
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."