Here’s Who Thinks Colbert Will Fail on ‘Late Show’

It seems that the third time was the charm for Stephen Colbert in getting a job on David Letterman’s Late Show, as the comedian and current host of Comedy Central’s The Colbert Report revealed that he tried two times to work for the long-running talk show before being announced as Letterman’s replacement earlier this month. Colbert appeared as a guest on the Late Show on Tuesday evening and said that twice earlier in his career he had tried to get a job working for Letterman.

The first time was for an unpaid internship with Letterman’s old NBC show, which he was offered in 1986, while in college. He didn’t take it “because you do not pay people. It’s an expensive city. The next job I’m taking here, that pays, right?” Colbert joked. The second time was in 1997, when Colbert and his writing partner, Paul Dinello, submitted a writing sample to Letterman’s show when Letterman was looking to hire writers – but the Letterman camp didn’t get back to them before their quirky Comedy Central show, Strangers With Candy, starring Amy Sedaris, got picked up.

Colbert brought along his sample “Top 10″ list that was submitted to try and get a job on the show, complete with his own blue cards. Colbert read the “Top 10 Cocktails for Santa” list and joked that his writing wasn’t at its best back in 1997.

Meanwhile, Fox’s right-wing alternative to Letterman, Bill O’Reilly, has skewered CBS’s decision to hire Colbert. “Colbert has made a living exclusively satirizing the right,” O’Reilly said Monday night on The O’Reilly Factor. He doesn’t think that Colbert will be able to compete with more vanilla hosts like Jimmy Kimmel and Jimmy Fallon, who head competing talk shows, because his persona on The Colbert Report has so deeply alienated conservatives.

Of course, O’Reilly and Colbert have been at talk show war for years, as Colbert’s persona openly mocks right wingers like O’Reilly. O’Reilly has said that The Colbert Report “owes everything to me.” Both have appeared as guests on each other’s shows and have publicly lambasted each other’s opinions.

O’Reilly said that Colbert will have to prove himself as much better, funnier, and more popular than the “sharp and well-produced” Kimmel and Fallon shows in order to succeed. “Colbert will have to be better than those guys to compete in the ratings. And remember, he’s already alienated 40 percent of the country who define themselves as conservative,” O’Reilly said. “In the end, Colbert may prevail, but my analysis of him has been to the point and honest.” That last part seems pretty doubtful, but he could be right that Colbert’s image is too extreme to appeal to the broadest possible swath of Americans that the Late Show is meant to appeal to.

It was rumored that Colbert would receive the position on the Late Show before the announcement was made. CBS hired the subversive and hilarious host as a way to make network late-night TV more engaging for a younger audience, which Colbert has definitely nailed over at Comedy Central. Sadly for fans of The Colbert Report, Colbert has decided to make the seemingly lateral move to CBS rather than stick with Comedy Central and his mocking right-wing persona. It’s safe to say that this time, CBS probably offered to pay him.

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