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Four Times Stephen Colbert Got Extra Real

None of us turn on late night TV to be challenged. Or, at least, if you do, you’re likely to walk away disappointed. Late night show hosts are men and wome—well, men who usually know their job is just to keep you from flipping the channels with some celebrity guests, goofy gags and maybe a cool band at the tail end of the show.

So, you know the drill. If you tune into Jimmy Fallon you’ll either see stars engaging in the dumbest game you could possibly imagine or Fallon inexplicably cackling on a guest comment that may or may not have been an actual joke. If you tune into Kimmel, you get some snarky current news commentary. And if you turn on Colbert? Well…

Colbert likes to position himself as the adult in the room, often presenting a (slightly) more cerebral take on the news and pop culture events than his peers. It’s an interesting trajectory from the man once known for his astonishing hyper patriotic conservative news satire performance. Back then, you never quite knew where performance ended and reality began. On The Late Show With Stephen Colbert, the question is how real things are going to get.

Because Colbert is far and away the most likely late night host to really go there with his guests. More so than most public figures, Colbert was shaped by tragedy. He lost his father and two brothers in a plane crash when he was 10 years old, an experience which clearly drove him into deep dependance on his Catholic upbringing. He’s opened up about that loss and the more recent loss of his mother with guests, sometimes sharing profoundly human moments in front of a live studio audience.

Here are some of Colbert’s most real moments.

Talking to Anderson Cooper About God and Grief

Cooper, like Colbert, is no stranger to grief. Cooper also lost his father when he was a child, and his brother committed suicide a few years later. When Cooper interviewed Colbert, he asked about a Tolkien quote that Colbert has expressed admiration for: “What punishments of God are not gifts?”

“Do you really believe that?” a visibly moved Cooper asks Colbert.

“That’s the great gift of the sacrifice of Christ, is that God does it too,” Colbert tells Cooper. “That you’re really not alone.”

Explaining the link between faith and comedy to Dua Lipa 

Dua Lipa briefly took the reins from Colbert to ask him a few questions, including how his faith informed his comedy. Colbert had a thoughtful and poignant answer ready to go.

“If there’s some relationship between my faith and my comedy, it’s that no matter what happens, you are never defeated,” Colbert says. “You must understand and see this in the light of eternity and find some way to love and laugh with each other.”

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Telling Oprah about his favorite Bible verse

Colbert shares a great story with Oprah Winfrey about a period of spiritual darkness in his life when he happened to pick up a Bible from someone who has handing them out for free. He opened it at random to Matthew 6:27, which has become his favorite verse.

“It changed my life,” he said. “I had lost my faith, I was so racked with anxiety. It was the first time I had read the Bible and I understood the phrase, ‘It spoke to me.’ The words of Christ are that for me. The words of Christ just speak off the page. There’s no effort for me to read them.”

Exploring insecurity with John Mulaney

This is a little less obviously spiritual than some of the other entries on this list, but it’s still fascinating. Back before Mulaney’s well-publicized rehab stint, he appeared on Colbert where the two started talking about their impulses to get into comedy. At around the 6:25 mark in the video, Colbert, sensing an opening, asks Mulaney if he uses humor to keep people at a distance — a question that clearly stuns Mulaney, leading to a long, remarkable pause in which Mulaney appears to tumble down a deep well of introspection before asking Colbert the same.

“There are a lot of people out there who I know don’t like me because of the sometimes-divisive nature of the jokes I make,” Colbert responds.

“Does that feel personal?” Mulaney asks.

“No,” Colbert says. “What feels personal is the connection I make with the people who do appreciate the jokes. And beyond that I’m just doing my job and I wish no one harm. And if some people don’t like what I do, I don’t like that but it’s not my problem.”

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