As if going to prison wasn’t bad enough, Lil Wayne had a rough day at the dentist, undergoing a harrowing eight root canals in one sitting.

Sources tells TMZ that Weezy stayed strapped to the dentist’s chair for a marathon oral surgery on Thursday (Feb. 18). During the eight-hour procedure, he had his signature grill worked on, several tooth implants redone, more implants added, and his real teeth repaired.

The operation is what delayed the rapper’s one-year jail sentence. He was expected to start serving his time on February 9, but will now report to prison on March 2 after he recovers.

“It is a medical situation that, like [for] any of us, has to be addressed,” his lawyer Stacey Richman said last week. The dental surgery had been planned prior to his court date, but was postponed because his dentist was out of the country.