In perhaps one of the most memorable episodes from Season 7, Woody gives Kelly the gift of music. And Phoef Sutton (who scripted the episode) gives us the gift of genuine comedy.
Whenever I watch this episode, I'm reminded of certain events in life that we are know are about to happen but are not able to do anything about it. This feeling of comedic dread (when the event itself is silly but also tragic and/or embarrassing) is such a unique feeling. It's one of those genuine, indescribable lumps in the throat. When Woody sits down to sing Kelly her song, the lump in the throat involuntarily grows. We know the song will be simple, innocent, somewhat naive. We know the song will be sneered upon by the richer crowd. And we know that Kelly will not understand that that is Woody's gift. But we watch anyway, and we laugh even though we know what will happen. I always think of this as "one road comedy", sort of Socratic philosophically and (even) artistically.
It's like calling the movie "Road to Perdition" predictable. It's predictability is the entire point of the film -- it's in invalid criticism since it is the predictability of the movie's events that make the events of the film so tragic. And while the feelings evoked from "The Gift of the Woodi" are entirely different in tone, the means by which those feelings are created are exactly the same. The inevitable, predictable events of Woody's song are what make the events so comedic.
An avid Cheers fan will instantly recall this scene whenever the words "Kelly, Kelly, Kelly, Kelly" are uttered. Once you have seen this scene, it will forever be etched in your mind. This, to me, is a sign of brilliant comedy. Cheers was not a simple sitcom with one-dimensional characters. Most, if not all, episodes of Cheers had a complex structure with many methods of comedy that utilized talented actors in subtlely complicated roles. Sometimes the comedy was in situation (as in this episode), sometimes the comedy was physically presented, and sometimes the comedy was in the interaction of two or more characters.
Whatever the case, the folks involved with Cheers knew how to make people laugh. And an episode like this is just one of the many ways in which it helped us do so.