Ain't No Sunshine - Bill Withers
In the beginning of chapter 11, Holden finds himself thinking about Jane Gallagher and reflects on his past experiences with her. He thought about how much fun he had with her and stated "you never worried, with Jane... All you knew was, you were happy" (Salinger 79). After he finished thinking about Jane he becomes depress and decides to go to a night club. Holden became depress because he missed Jane and how being with her made him feel happy. Bill Withers "Ain't No Sunshine" fits this scene perfectly. In the song he sings "It's not warm when shes away, Ain't no sunshine when she's gone." Bill talks about missing a girl and how he feels depress without her presence which is how Holden feels about Jane.
Alone Again (Naturally) - Gilbert O'Sulivan
In chapter 9 Holden gets off a train and decides to go to a phone booth to call someone. Once he is inside the booth he has trouble deciding who he wants to call and makes excuses on why he can't call certain people. He then decides not to call anyone and just stands alone in the booth for "about twenty minutes or so" (Salinger 59). In Gilbert O'Sullivans song "Alone Again", a few lines in the song describe Holdens scene in the phone booth, "In my hour of need, I truly am indeed, Alone again, naturally". He is feeling lonely and wants someone to talk to but realizes he can't because it's late which makes him feel more alone.
Wandering Star - Portishead
In Chapter 12 Holden is on his way to a night club in taxi cab. On his way there he notices all these couples on the street laughing and having fun and it reminds him that he is "lonesome and depressed" (Salinger 81). In "Wandering Stars" by Portishead, the lines "for its such a lovely day, to have to always feel this way, and the time that i will suffer less, is when i never have to wake" matches the tone of the scene and Holden's level of depression he has throughout the story.
Stressed Out - Twenty one Pilots
In Chapter 16 Holden decides to go to a museum he visited when he was younger and while he is on his way there he thinks about all the times he used to go there when he was a kid and how he has changed over the years. He explains how in the museum, the displays didn't change "you could go there a hundred thousand times" and they wouldn't be different "the only thing that would be different would be you" (Salinger 121) and that he is the one that changed. He would grow mentally and be more aware of things each time he returns. Holden gives us examples of this when he tells us about a time he heard his parents fight in the museum and how he passed by "one of those puddles by the street" and noticed it was gasoline. He is no longer the oblivious and innocent kid he once was but he wishes he still could be and states "certain things they should stay the way they are" (Salinger 122). The song "Stressed Out" would fit this scene because it talks about the transition from childhood to adulthood and the artist in this song says "wish we could turn back time, to the good ol' days" which relates to Holden because he doesn't want to grow up and he wishes he could be a innocent kid again.
Take the Money and Run - Steve Miller Band
At the end of chapter 7 Holden decides to leave Pencey to spend a few days at a hotel in New York. He packs all his things and counts all the money he has before he goes and mentions that he "was pretty loaded" (Salinger 52). Steve Miller Band song "Take the Money and Run" fits in with the scene because the lyrics say "go on take the money and run(x4)" which is basically what Holden is doing. He's gather all his money and running away from Pencey and all the people that annoy him like Stradlater and Ackley.