Pictures David Letterman's Greatest Musical Guests April 28, 2015 / 9:00 AM MDT / CBS News Letterman's Greatest Musical Guests - Ray Charles Letterman's Greatest Musical Guests - David Bowie David Bowie performs on the Late Show with David Letterman, September 25, 1995 on the CBS Television Network. This photo is provided by CBS from the Late Show with David Letterman photo archive. Photo: Alan Singer/CBS ©1995 CBS Broadcasting Inc. All Rights Reserved Letterman's Greatest Musical Guests - The cast of RENT Prince Prince (credit: Alan Singer/CBS ©1996 CBS Broadcasting Inc. All Rights Reserved) Letterman's Greatest Musical Guests - Tina Turner Letterman's Greatest Musical Guests - Dave Matthews Band Letterman's Greatest Musical Guests - Bruce Springsteen and the E Street Band Letterman's Greatest Musical Guests - Simon & Garfunkel Letterman's Greatest Musical Guests - The Beastie Boys Letterman's Greatest Musical Guests - Gwen Stefani Letterman's Greatest Musical Guests - Madonna Letterman's Greatest Musical Guests - Pearl Jam Letterman's Greatest Musical Guests - Christina Aguilera Letterman's Greatest Musical Guests - U2 Letterman's Greatest Musical Guests - Paul McCartney Letterman's Greatest Musical Guests - Brooks & Dunn and Reba McEntire Letterman's Greatest Musical Guests - EMINEM and JAY-Z Letterman's Greatest Musical Guests - Elvis Costello Letterman's Greatest Musical Guests - Darlene Love Letterman's Greatest Musical Guests - Lady Gaga Letterman's Greatest Musical Guests - Cher Letterman's Greatest Musical Guests - The Flaming Lips with Sean Lennon Letterman's Greatest Musical Guests - The Black Keys Letterman's Greatest Musical Guests - The Foo Fighers Letterman's Greatest Musical Guests - Taylor Swift Taylor Swift performs on the CBS Late Show With David Letterman October 28, 2014 on the CBS Television Network. This photo is provided by CBS from the Late Show with David Letterman photo archive. Photo: John Paul Filo/CBS ©2014CBS Broadcasting Inc. All Rights Reserved