On the Outside Looking In may refer to:
On the Outside Looking In (album), a 1994 album by Eightball & MJG "On the Outside Looking In" (Friday Night Lights), an episode of the TV series "On the Outside Looking In", a song recorded by Flanagan and Allen and Harry Roy & His Orchestra "I'm on the Outside (Looking In)", a 1964 song by Little Anthony & The Imperials ""Outside Looking In", a 2006 song by Jordan Pruitt