20 Funniest Community Moments Of All Time
2. Kiss From A Rose
Email hacking, black mail, Mexican for lunch; these are all tactics that Dean Craig Pelton used to spend a day with Jeff Winger in an attempt to create a friendship (and maybe more). Jeff pretends to be sick to get out of helping Annie move, and the Dean uses this information to his advantage, culminating in probably the best karaoke rendition of the Seal classic "Kiss from a Rose" of all time.
At first Jeff is predictably not into the forced karaoke jam, but as the song goes on he slowly finds himself becoming entrapped by the lyrics until he's belting them out right along with the enthusiastic Dean. The earnestness of the moment is what really sells the whole thing, which makes the revelation that the Dean orchestrated the whole thing to get some time alone with Jeff all the more entertaining.
Key Quote: "You know this one, Jeff. Weve sang it a thousand times together in my mind." - Dean Pelton