These Are David Letterman’s Most Contentious and Uncomfortable Interviews By Jared T. Miller From Oprah to Madonna, David Letterman’s Late Night interviews in the 1980s yielded some of his funniest — and most awkward — moments. Read More Tags: original video david letterman late night with david letterman madonna oprah winfrey More Apr. 3, 2017 Watch Now David Letterman’s Most Uncomfortable Interviews