When it comes to late-night talk show hosts, Johnny Carson, Stephen Colbert, and Jon Stewart are among the most revered and respected figures in television history. A new ranking from DraftKings has reignited debate among fans by naming a new king of late night.
With so much attention surrounding Stephen Colbert’s exit from late night, comparisons are naturally being made as the legacy of The Late Show with Stephen Colbert is cemented. Colbert will go down in talk show history as one of the smartest and most influential hosts of his generation, but the new rankings place a different late-night comedian at No. 1.
While many rankings place Johnny Carson at the top of the list, writer Andy Silva ranked David Letterman as the greatest late-night host of all time, writing:
“Audiences watched Letterman evolve from hosting the anti-talk show with Late Night beginning in 1982 to being the format’s elder statesman and spokesperson, showing the others it was alright to be funny again with his much-heralded comments on air following the September 11 attacks.
“Initially, Letterman was given strict rules by Johnny Carson to differentiate Late Night from The Tonight Show, including no big band and no monologue. But that was fine with Letterman and his team, including the brilliant Merrill Markoe.
“Letterman’s Late Night didn’t so much want to be part of the entertainment establishment as skewer and deconstruct it. Innovative bits like the Monkey Cam, the famous Velcro suit, and the 360-degree rotating show all made clear that this was no ordinary talk show. And fans loved it, making Letterman and his sharp, sardonic wit red hot through the 1980s and 1990s.”
David Letterman Ranked the Greatest Late-Night Host of All Time
The ranking arrives at a moment when late-night television is once again dominating entertainment headlines. Following CBS‘s cancellation of The Late Show with Stephen Colbert, fans and journalists alike are reflecting on the personalities who shaped late night and influenced generations of viewers.
Letterman doesn’t claim the top spot solely because of his iconic interviews—who could forget Drew Barrymore‘s impromptu birthday dance? Nor is it simply because of the groundbreaking musical acts he introduced to audiences. The Indiana native earned the honor because he transformed what late-night television could be.
Rather than following a traditional formula, Letterman reinvented the genre with unconventional comedy, absurdist sketches, and a willingness to poke fun at everyone from political figures to network executives. His style helped pave the way for future hosts such as Stephen Colbert and Jon Stewart, who would go on to blend comedy with cultural and political commentary.
Why David Letterman’s Legacy Still Resonates Today
More than a decade after retiring from late-night television, Letterman’s influence remains unmistakable. He wasn’t simply chasing laughs or booking the biggest celebrities. He combined wit, self-aware humor, quirky recurring segments, and sharp observations about culture to create a format that countless hosts would later emulate.
Many of today’s most recognizable comedians and television personalities cite Letterman as a major influence. His willingness to challenge expectations and experiment with the format helped redefine what audiences expected from a late-night host.
How David Letterman Changed Late-Night Television Forever
From his famous rivalry with Jay Leno to his public frustrations with CBS executives, Letterman often positioned himself as the outsider among late night’s biggest stars. That underdog persona became a defining part of his appeal.
Decades later, his impact on television remains undeniable. Whether fans agree with every ranking or not, Letterman’s influence on comedy, talk shows, and popular culture continues to shape the genre.
Judging by this latest ranking, David Letterman is no longer late night’s most underappreciated host. He may now be considered its greatest.
Related: Stephen Colbert’s Final ‘Late Show’ Marks End of an Era With Emotional Message
This story was originally published by Parade on Jun 4, 2026, where it first appeared in the Entertainment section. Add Parade as a Preferred Source by clicking here.
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