Best Musical Moments of The Late Show With David Letterman

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  • James Brown
  • Whitney Houston
  • Will Smith
  • George Clinton
  • Beastie Boys
  • Lady Gaga
  • Lauryn Hill
  • Jay Z and Eminem
  • Le1f
  • Kendrick Lamar
  • J. Cole
  • Kanye West
  • Lettermen is Leaving

Will Smith

One of hip hop's most iconic songs, Will Smith and DJ Jazzy Jeff’s "Summertime," may have come out in 1991, but more than 20 years later Smith proved he could still "sit back and unwind" with an impromptu performance of his Grammy Award-winning hit. Paul Shaffer and the band welcomed Smith to the show by playing the '90's classic, inspiring Big Willie to grab a mic and take a blast to the past.


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