I'd get the Essential Bruce Springsteen 3 disc set. While there are many great songs missing, it does quite a good job of condensing Bruce's sound from the different eras of his career, and helps you find focus. I also agree with Terri and Kathleen about the live recordings, especially the Live '75-'85 set. Live In NYC, while amazing, is more of a die hard album. As far as studio albums, Born To Run is absolutely essential. Darkness on the Edge of Town, Born In The USA, and The Rising round out my personal Top 4.