While "Dream a Little Dream of Me" used a sequence of songs to set a mood in the story, The Squid and the Whale uses the repetition of a single song to explore a theme.
The Squid and the Whale deals with the divorce of Bernard and Joan Berkman and its effects on their sons Walt and Frank. Walt, a highschooler starstruck by his author father, decides to assert his own genius by writing a song.
The problem is that the song he wants to write has already been written by Pink Floyd: it's "Hey You."
The song is introduced as Walt practices it in his room, played again when he shows his "composition" to his parents, and takes center stage when he "debuts" it at his school's talent show.
The lyrics--"Hey you, out there in the cold...can you feel me?"--seem to start as Walt's triumphal offer of hope to the people feeling lost around him, but after he is exposed as a fraud the nature of the song changes as he himself becomes lost.
The tonal shift which the movie's circumstances give the songs is dramatic, but what is most interesting is to see how one song can represent both sides of Walt so well. On the one hand, it allows him to present a facade of confidence, but on the other it represents his deepest insecurities--his uncertainty that anyone is listening to him.
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