Remy loses a tooth during a Red Sox game
While the Red Sox were on their way to losing a slugfest against the visiting Chicago Cubs in 2014, Remy was busy losing his tooth.
During the fourth inning of the game at Fenway, the conversation in the NESN booth pivoted from the game to Remy’s tooth, which had somehow popped out in the middle of the broadcast. He and Orsillo would spend the better part of the remaining game hysterically laughing as they joked about what to do with the tooth.
Orsillo encouraged his partner to try sticking the tooth back in, even offering to assist in the minor operation.
"“You’re not going in my mouth,” said Remy."
That led to Don outlining how he would use his dentistry skills to hammer the tooth back in. Naturally, he would need some plyers to separate the other teeth to make room for him to “bang it in.”
Someone from the production team actually handed Orsillo a bag of tools, including plyers that he used to try to wedge the tooth back into place. Remy tried to explain that it was set back in wrong and was poking sharply into his gums.
"“Don’t worry about it, it’ll be fine,” Orsillo responded confidently."
When he couldn’t find a hammer to finish the job, Don’s last resort was to try using tape to hold the tooth back into place. Sure, that will fix everything!
The ridiculous interaction between the two broadcast partners was comedic gold. No pair covering the Red Sox for NESN has ever had better chemistry together than Don and Jerry. Even when games started getting out of hand, those two could be counted on to keep fans entertained.
This iconic pair had many great moments together but the tooth debacle was mentioned by Orsillo as being his favorite, which means it undoubtedly deserves a spot on this list.