Looking Over My Shoulder by Elliott Smith explores themes of paranoia, regret, and introspection. The lyrics delve into the complex emotions of constantly feeling watched or judged, possibly reflecting on past mistakes and the repercussions they bring. The song captures a sense of vulnerability and the struggle with personal demons. Particularly poignant moments include the recurring imagery of looking over one's shoulder, which symbolizes the inescapable nature of one's own conscience and the anxiety that accompanies it.