David Letterman – 74

David Letterman was late-night royalty for 33 years straight and was once named one the greatest TV stars of all time. Before his massive success with his late-night talk show, he starred in his own namesake morning comedy show in 1980. Two years later, Letterman solidified his Hollywood status to a permanent degree when he began hosting Late Night with David Letterman over at NBC. Eventually, when he transferred to CBS, he also became the showrunner of the Late Show with David Letterman.

Now he has happily retired from the TV platforms and has been offered other projects by big companies like Netflix. In 2018, he even began hosting the series My Next Guest Needs No Introduction with David Letterman. The show currently has three seasons featuring big names like Jay-Z, Barack Obama, and George Clooney. He interviews celebrities both inside and outside a studio setting, a different format than what the host is known for.