David Letterman held his reign as a late night host for over 30 years before handing off the Ed Sullivan theatre to successor Stephen Colbert. If somebody were to watch one of Dave’s shows in his final years, they would probably question why people let him on the air. As he aged into his 60’s his delivery became slow and often tame, but his quick wit and ruthless interrogation was broadcasted to his dedicated fanbase of millions 5 nights per week.
David Letterman didn’t care about preserving a crystal image, ever since his early days at NBC, he made his niche in the world of late night television not by being calm, cool and collected like his show’s lead-in Johnny Carson, but an erratic, quirky and innovative host who often put their guests in the hot seat. Sometimes that seat was so hot that guests would threaten to leave or vow to never return to the show, that list including the 2016 GOP front-runner Donald Trump.
Trump made over a dozen appearances on Letterman’s show over the decades, and Letterman did not let a single opportunity go to waste to roast Trump like the ham that he is. Every single appearance Letterman would ask Trump how much he was worth, and much like today, that number was very wishy-washy. Here is the best of Letterman vs. Trump on wealth: