When Stephen met Dave: The path to Colbert’s Letterman succession

Stephen Colbert will replace David Letterman on CBS late night sometime in 2015. The news was met with cheers by many, jeers by a few, but most important, it apparently has the blessing of Dave himself.

In a statement released Thursday morning, shortly after the network confirmed Colbert’s appointment, Letterman said: “Stephen has always been a real friend to me. I’m very excited for him, and I’m flattered that CBS chose him. I also happen to know they wanted another guy with glasses.”

Though Letterman has never appeared on “The Colbert Report,” Colbert has been a frequent guest on “Late Show.” He’s been on 12 times since 2005, the year his Comedy Central show debuted.

VIDEO: Stephen Colbert out of character

His very first appearance on “Late Show” was Sept. 2, 2005, ahead of his “Colbert Report” debut and it seems to be Colbert as himself and not the conservative character he honed and perfected on his show.

The two discussed Colbert’s very large family (Colbert was one of 11 brothers and sisters) and his recent sea voyage to Bermuda. From the start, Letterman clearly enjoyed Colbert’s humor and storytelling ability. What would Colbert be doing on his new show, Letterman asked.

“Changing the world,” Colbert responded.

Colbert was in character for his November 2008 appearance promoting his upcoming Christmas special. While Barack Obama had recently won the presidency, Colbert had not given up on the Republican rival, John McCain.

“It’s not over, Dave,” Colbert declared. “McCain can pull this thing out.”

He went on to explain: “It’s gonna be a rough couple of news cycles for him. Fundraising is going to dip at this point.”

Letterman was still enamored of Colbert’s large family upbringing and quizzed him about Christmas at the Colbert house.

Colbert stopped by “Late Show” in October 2010 shortly after his controversial testimony before Congress on his experience in the fields with the United Farm Workers. The appearance was notable because Colbert chose to testify as his character, which made for humorous TV, but many congresspeople were unamused.

“What kind of stuff did they ask you?” Letterman wanted to know.

“Why are you here?” Colbert responded.

Seven years after his first appearance, Letterman was calling Colbert “my friend” on camera and, like old friends do, they were still chatting about the same stuff they’ve talked about for years. In the case of this 2012 appearance, Letterman was still curious about the large boat race to Bermuda that Colbert participates in.

“And you love to sail?” Letterman asked.

“I don’t know much about it,” Colbert replied.

“Then what are you doing?” Letterman demanded.

“Because as I said to you seven years ago, I get to be away for a week and my wife says it’s OK!” Colbert said.

More recently, Colbert has graduated to appearing on “Late Show” in costume and in character, usually the kind of stunt reserved for longtime friends of Dave such as Bill Murray. During a 2013 appearance, he came prancing out as a Dickensian beggar.

While discussing his cameo appearance in “The Hobbit,” Colbert pointed out his one pointed ear to the host.

“Once I show you this, you can never unsee it,” Colbert said.

After demonstrating the off-kilter ear, he turned to Letterman and asked: “Am I hideous to you now, Dave?”

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