Funniest late night show host: Jimmy Kimmel or David Letterman?
via AP

Funniest late night show host: Jimmy Kimmel or David Letterman?

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David Letterman and Jimmy Kimmel are the kings of two very different eras of late night shows. Letterman represents the old guard—his career span 33 years in TV and was capped with a triumphant retirement. Kimmel is the latest iteration of the late night show. Originally the outsider to late-show network comedy, Kimmel has quickly become the reigning king with his commitment to pranks, stunts and viral videos. But who is the best?

The Votes Are In!

After a year like 2016, we could all use a laugh. That's why we've taken 16 of the most beloved comedians of all-time and are pitting them against each other all month long! Who's the funniest? You decide and we'll announce the king (or queen) of comedy at the end of the month!

Help us crown the best comedian by voting in these other exciting head-to-head debates too:

Biggest comedy empire: Dave Chappelle or Kevin Hart?

Best comedian with a sitcom: Jerry Seinfeld or Margaret Cho?

Funniest self-deprecating stand-up: Louis C.K. or Hannibal Burres?

Best political commentary: George Carlin or Jon Stewart?

Best comedy act: Stephen Colbert or Steven Martin?

Most groundbreaking comedian: Joan Rivers or Samantha Bee?

Funniest comedian-turned-director: Mel Brooks or Woody Allen?


No comedian has had as large of role in shaping contemporary comedy than David Letterman. The veteran was the undisputed king of the late night show before he retired, and inspired generations of comedians.

He's leaving as the champ, of course: Maybe not Sandy Koufax, quitting after a 27-win season, but at the very least Ted Williams, hitting dingers in four different decades. He changed not just late-night TV but the very nature of comedy itself. Self-awareness, Stupid Pet Tricks, sneakers, irony: He taught multiple generations what it means to be funny. "Everything about his show informed not only our writing but our actual human interactions," says Tina Fey, a Letterman fan since his short-lived morning show in the summer of 1980, when she was 10. Sixteen Emmys and a few thousand Top Ten lists later, even Jay Leno has acknowledged that Letterman's the better broadcaster. At this point, it's Copernican: settled science.

Few can compare to David Letterman's legacy. 

Jimmy Kimmel represents a more whimsical side of late night comedy that didn't exist before him. No matter what he does, it's all in good fun, and all are welcome on his show. Kimmel was the first comedian to truly bridge the digital divide. His work has earned over one billion views on Youtube, and he's done it simply by making good TV. 

Kimmel’s recent fake videos — the wolf that didn’t really prowl the halls of the Sochi Olympics, the girl who didn’t really set herself aflame while twerking — are the most recent examples of his digital savvy. But he’s been displaying it for at least five years, when his show embraced YouTube; his official channel is just about to hit a billion views.
It’s sort of astonishing that we now take Kimmel’s success on the Web for granted: The idea of a broadcast TV star letting people watch his best stuff somewhere other than TV would have unthinkable just a few years ago. Now, it’s standard practice.

Kimmel absolutely kills it on YouTube, and has reached viral stardom in ways few comedians have been able to match. Here is one of his most popular video bits. 

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