Many songs from the College Drop-Out album by Kanye West relate to The Catcher in the Rye. This album explores some of the bitterness that Holden feels regarding cultural assumptions and generalized expectations. There is also commentary on the value and nature of conventional education, especially higher education.

There are so many songs about feeling alienated, but the song that first came to my mind was “Watching the Wheels “ by John Lennon.  I guess that is a bit of a morbid suggestion!  However, the song does have a kind of melancholy reflectiveness to it.  You can read the lyrics here:

http://www.oldielyrics.com/lyrics/john_lennon/watching_the_wheels.html

InThe Catcher in the Rye, Holden's loneliness remains a major theme throughout the novel.  He attempts to solve his feelings of alienation through companionship, but ultimately his lack of people skills and genuine insecurity undermine his ability to develop relationships on a deeper level. 

A rap or hip-hop song that relates to the theme of loneliness in The Catcher in the Rye, and especially Holden's feelings of isolation is Drake's "I Get Lonely Too."  The lyrics definitely reflect Holden Caulfield's wishful attempts at finding someone to connect with:

Take Me,
to another place where I’ll be
face to face, just you and me
with no rules, just like you
I get lonely too ("I Get Lonely Too")

Holden would rather be in "another place" as Drake's song suggests, a place free of the difficulties and confusing "rules" of adulthood.  In the lyrics from Drake's song, Holden could envision himself in the pastoral scene from "The Catcher in the Rye" song, safe in his childish dreams and not wanting for companionship.