These Are David Letterman’s Most Contentious and Uncomfortable Interviews

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From Oprah to Madonna, David Letterman’s Late Night interviews in the 1980s yielded some of his funniest — and most awkward — moments.

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  1. ‘Foo’ or ‘Fool’? A Chat With the Cast of This Fool
  2. The Afterparty Cast Will Get That Edwin McCain Song Stuck in Your Head
  3. A Send-Off for Search Party
  4. Henry Winkler Demonstrates Why He’s a Better Acting Teacher than Gene Cousineau
  5. Taylor Garron and Chanel James Made a Whole Movie From Separate Homes
  6. Matthew Rhys Walks Us Through Getting Humped Off a Bed
  7. Sam Richardson Is Daddy and He Is Familiar (With Guns)
  8. Tom Stourton’s Face was Not Allowed to Play Edward Snowden
  9. Elijah Wood Is Just a Really Nice Guy, Honestly
  10. Michael Ian Black Owns a Robot Car
  11. Allow Selling Sunset’s Mary Fitzgerald to Convince You to Move to L.A.
David Letterman’s Most Uncomfortable Interviews