20. David Letterman
David Letterman spent 33 years (longest tenure in talk show history) hosting innovative late-night TV for America’s delectation before turning over Late Show to Stephen Colbert in 2015. Notoriously self-flagellating and compulsively anti-romantic, Letterman was never truly comfortable unless he was seething with unhappiness at something. Irreverent, offbeat, and entirely original, Letterman’s ironic, ‘everything-is-stupid’ style helped usher in a new approach to comedy that is the norm today.
Image Source: Variety