While millions of viewers are familiar with his "Colbert Report" personality, Howard wanted to get to know the "real" Stephen Colbert during this morning's interview.
Check out some highlights from Howard and Stephen's wide-ranging talk (below).
An Early Tragedy
Howard asked about Stephen's father, an incredibly smart man who worked in the medical field, first as an immunologist and later in other specialties. "I think he was the youngest medical school dean ever," Colbert explained.
Tragically, when Stephen was 10 years old, his father and two brothers died in the infamous crash of Eastern Air Lines Flight 212 that ultimately spurred the Sterile Cockpit Rule because of what was heard on the black box recorder -- the pilots were distracted talking about politics and an amusement park among other topics.
The loss, of course, left a painful mark on Stephen and his surviving family members. "It's built into me the way like, the marble is built into the shape of a statue … It's kind of, at a certain age, what I was made of," he recalled.
Colbert said that he didn't actually read the transcript until a couple of years ago and only by accident. He has never heard the audio and doesn't want to.
Howard wondered if the experience of consoling his mom shaped his comedy career in a way. Stephen said that he would often joke that he raised his mother after that. "There's no clean description of what life was like."
"Is it difficult for you to be around a crying woman now because of your mother?" Howard asked.
"Wow, that's deep man … I think there's no doubt that I do what I do because I wanted to make her happy. No doubt," Colbert concluded.
Replacing David Letterman
On the subject of his new late night show, Colbert told Howard that he didn't really care about ratings. "I want to do the best show I can, you know? Mathematically I'm taking over for Dave. I was given that. That is not something that, you know, I angled for … I didn't plot to do it," Stephen added.
"You can't take over for Dave. You can take over for that time slot, but that's it. Dave created 'Late Show.' We have to call it 'Late Show,' but it's kind of crazy to call it 'Late Show.'"
Asked if he would change the name, he said that he didn't have the choice, but he would have thought about it for sure. "I think it's more respectful to Dave to keep it 'Late Show,'" he concluded though.
Jimmy1, Jimmy2, and Conan
Despite constant prodding from Howard, Colbert wouldn't allow himself to delve into the cliché late night battle scene. He said instead he's friends with "Jimmy1," "Jimmy2," Conan and the rest of his competitors.
"CBS is competing with NBC and ABC and TBS or whoever it is. You know, Conan and Jimmy-one and Jimmy-two as I call them, are friends."
Which Jimmy is which, you may ask? He wouldn't reveal it, only telling Howard that they knew who they were.
Visiting Les Moonves' House
When asked if he has been to CBS President/CEO Les Moonves' house, Stephen said he had recently and was joined by friend of the Stern Show Vinnie Favale.
Colbert took Les through what a typical show might go with him along with the opening credits and some other early footage.
The Road To Stardom
Stephen and Howard tracked his early career from Second City in Chicago, where he answered phones and helped out in exchange for free classes, to "Exit 57," "The Dana Carvey Show," a brief stint writing for "SNL," and a few other iconic gigs.
But the road was not easy in the least bit, Colbert remembered. Between "Exit 57" getting canceled right before he had to a baby to the unsuccessful run of "The Dana Carvey Show" that brought him to New York City, Colbert worked incredibly hard to stay above water and learned a lot along the way.
The Original Onion News Anchor
Colbert also recounted the story of how he was the original Onion News Anchor.
"This is something people don't know is that when I was at the 'Carvey Show,' the Onion was still pretty young. We were going to do the Onion News on Carvey. I was the anchor for the Onion News. We actually shot it with the little Onion symbol, you know. I remember the one thing I did was like, 'Area Bowl Cashed.' We threw live to a press conference of two stoners announcing that their bowl was cashed and their plans to repack the bowl."
Coincidentally, Good Morning America had seen that clip and thought he looked like a straight news anchor who could actually be funny -- but in the end he only did one segment for them, despite pitching more than twenty.
The 2006 White House Correspondence Dinner
You may remember back in 2006 Colbert hosted the White House Correspondence Dinner and proceeded to roast then-President George W. Bush amongst a crowd that simply was not having any of it. Though he doesn't remember it being as bad as the media portrayed it, he said the backlash was brutal with many letters getting forwarded to security personnel afterwards.
Stephen recalled how he had asked Jon Stewart beforehand if he should do it and they both agreed that he needed to. In the end he thought it went far better than those watching thought it went.