CBS+ David Letterman's Greatest Musical Guests April 28, 2015 / 5:00 AM CDT / CBS News Letterman's Greatest Musical Guests - Ray Charles Letterman's Greatest Musical Guests - David Bowie Letterman's Greatest Musical Guests - The cast of RENT Letterman's Greatest Musical Guests - Prince 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