Stephen Colbert Dares Donald Trump To Be A Guest On ‘The Late Show’ (And Other Highlights From ‘The Howard Stern Show’)

Stephen Colbert on Stern
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As the debut of CBS’s brand new The Late Show with Stephen Colbert approaches, it seems that the only person more excited and anxious than Colbert’s fans about his new gig is the host himself. In preparation for his September 8 return to late night television, Colbert is making the media rounds in a way that can only be described as Colbert-esque. In an essay for Glamour, he addressed the late night circuit’s status as a boys club or “sausage fest,” while he teased the Television Critics’ Association that his Late Show personality won’t be much different than his Colbert Report personality, but, more than anything, he’s eager to get in on the Donald Trump action.

For his GQ cover story, Colbert took us all behind-the-scenes of his makeover of the Ed Sullivan Theater, while also revealing the incredible attention to detail that he has overseen in making everything about his new home just right, not only for him but also his band leader Jon Batiste, and perhaps most importantly his guests. But, as we all know, when it comes to truly bearing one’s soul and talking about almost everything a person can talk about, the only place that matters is Howard Stern’s studio. Colbert was a guest on today’s episode of The Howard Stern Show, and the two beloved talk show personalities discussed everything from Colbert’s early gig as the frontman for a Rolling Stones cover band to his approach for this new job.

It was a truly wonderful, extensive interview, so obviously there were plenty of highlights and interesting tidbits (I will update with audio once it’s available), including a dare to Donald Trump…

“I would dare him to come on the show.” Colbert thinks that Donald Trump is “something of a brilliant figure.” He would love to have Trump on Late Show, because they’ve never had a problem with each other (that he knows of). What’s interesting about Trump, Colbert said, is that he’s a candidate with $10 billion, so he can go the distance and basically do whatever he wants. Meanwhile, Colbert has a standing dare for everyone to find out what happened to the money that he raised with his Super PAC, because he doesn’t think anyone can do that.

“I don’t have an ax to grind here.” Speaking of politicians, Colbert is glad that Jeb Bush is his second guest (after George Clooney), because he wants Republicans and candidates in general to understand that he doesn’t have an agenda. Earlier in the show, he also explained that The Colbert Report required him to be in character for 10 years, so there’s a chance that some people and politicians might not realize that, and he wants to have guests who understand that Late Show is not The Colbert Report.

Obviously, a lot of the interview dealt with Colbert’s new network gig, with Stern perfectly playing the roles of both inquisitor and devil’s advocate.

“I’m replacing two shows – Dave’s show and my old show.” Colbert said that he would have considered changing the name of Late Show, but that would have essentially been disrespectful to David Letterman. His approach to everything is humble and appreciative, as he told Stern, “You can’t take over for Dave, but you can take over that time slot. Dave created Late Show. We have to call it Late Show, but it’s kind of crazy to call it Late Show.”

“I’m not concerned about being No. 1 in late night.” Colbert never asks about ratings. As far as the classic late night rivalry, though, he had drinks with Jimmy Fallon when he got the gig, because they’re friends and he doesn’t see it as a competition. The network obviously sees it as a competition, but he doesn’t because it’s show business and he’s a performer.

“I don’t like to meet the woman before we make love.” While Letterman didn’t meet with his guests before each show, Colbert does plan to swing by the newly-created green room and meet his guests before they tape. Stern tried very hard to chisel away at the mystery of Colbert’s Late Show, but we really didn’t get too much out of it. For example…

“I’m not a stand-up.” Colbert’s monologues won’t be traditional stand-up comedy, but he also didn’t really explain what they’ll entail. He reflected on his career and background in sketch comedy a little, but everything is still a mystery ahead of that September 8 premiere.

“I got obsessed!” Colbert is “passionately attached” to this show because you can’t devote yourself to 202 hours of television a year and not be serious about it. More than anything, though, he seems to be most excited about introducing a wider audience to Jon Batiste and his band, Stay Human, because he is amazed by the amount of effort Batiste puts into preparing, as well. For the number-crunchers out there, Colbert estimates the renovations to the Ed Sullivan Theater at $10 million.

“I don’t have a target audience.” Colbert obviously hopes (and expects) that his Colbert Nation viewers will tune in to the new show, as if that’s even a question, but he also wants people who have never watched The Colbert Report to give him a chance. Even the people who hilariously failed with #CancelColbert are allowed to tune in to The Late Show to see if he’s still pissing them off.

“Tay Tay loves me.” Stern “will put money on” Colbert eventually resenting Fallon, because the people behind-the-scenes will steal his guests or a sketch, and then their friendship will be lost. Colbert, however, said that he would never lose someone like Taylor Swift to Fallon, because he has a note from Swift that says, “Love, Taylor. Not L-U-V, L-O-V-E.”

“I’ll try it on the other side.” Colbert met with Letterman for an hour and a half to discuss the new show, and his decision to put his desk on the other side of the stage from where Letterman had it comes from Letterman saying that he would have liked to have tried that. Aside from that, Colbert would love to have Letterman on as a guest, but he won’t reveal anything else about their conversation.

“I have a crew hat from The Chevy Chase Show.” As Stern reminded us, there are plenty of failed late night shows that serve as a warning that “sometimes networks can f*ck you,” like The Chevy Chase Show. Colbert actually wears a Chevy Chase Show hat around his office, not really as a reminder, but just because he has it. His CBS deal, in case you’re wondering, is for three years with an option for two more.

“F*ck you, old man.” Stern said that he loves Fallon and is close friends with Jimmy Kimmel, and that’s hard for him now that the three hosts are “knocking heads.” Stern has promised Kimmel that he’ll appear on his show next, but Colbert revealed that Kimmel will actually soon be a guest on Late Show. As for Stern, he will “of course” be a guest on Colbert’s show, but it’s genuinely hard for him because 1) he “hates” doing these shows, and 2) he is smart enough to see the competition between his three friends, even if they don’t. Colbert also offered Stern a preemptive “F*ck you” in case they are ever mad at each other.

Colbert’s life and career have been full of ups, downs, and tragedy, including the death of his father and brothers, which he discussed with Stern.

“The world didn’t make any sense.” When Colbert was 10, his father and two brothers died in a plane crash. The cockpit recorder from the crash of Flight 212 led to the “Sterile Cockpit Rule,” which required the pilots of any plane to only discuss the plane’s landing during that procedure, because the pilots of his father’s flight were talking about an amusement park and other pointless things. Colbert read the transcript from the cockpit recorder only a few years ago, and it was by accident because he didn’t realize that the rule was imposed because of that flight. “It doesn’t end well,” he said.

“We were called Shot in the Dark.” In high school, Colbert was in a Rolling Stones cover band that was terrible, and they actually called themselves, “Shit in the Dark.” Colbert opened the interview by singing “Brown Sugar,” and as a rock and roll frontman, Colbert makes a hell of a late night host.

“He was a great guy to improvise with.” At Second City, Colbert was able to work with Chris Farley a little, and he said that the late comedian was way more intelligent than he gets credit for. Craig Kilborn was at one point suspended from The Daily Show and Colbert, the “new guy,” was asked to fill in for that show, which just so happened to be on the day that Farley passed away. Colbert said he was “wrecked.”

“I wanted to work for Good Morning America.” Colbert didn’t necessarily like Kilborn’s The Daily Show, and he wanted his gig with Good Morning America to work out. Colbert only appeared on the show one time (above), but he pitched 25 ideas, and every single one of them was shot down. Unfortunately, those were the ideas that he originally wanted to use on The Dana Carvey Show for their Onion-inspired fake news sketches.

“I’m sorry I ruined your careers.” Colbert reflected on his writing job on The Dana Carvey Show, and how it was canceled in spectacular fashion as millions of people changed their channels during a terrible sketch in the first episode. The show’s writing team also featured Robert Smigel and Louis C.K., among others, but it was a complete disaster, and he was worried that he’d have a hard time finding work after that.

“Jim Carrey was attached.” Colbert and Smigel had a great idea for an Ambiguously Gay Duo movie, and Jim Carrey would have starred as Ace, and even gotten “jacked up” for the part. Carrey wanted Matt Damon for the role of Gary, but the movie just never happened. As Stern correctly pointed out, this is an idea that should be resurrected, and Colbert could see Jon Hamm starring in it now. YES-F*CKING-PLEASE.

“Don’t you make me love you, old man.” After his controversial hosting gig at George W. Bush’s White House Correspondents’ Association Dinner, Colbert said he “got a lot of letters,” implying that they were threats, but, of all people, Colbert said that Supreme Court Justice Antonin Scalia walked up to him afterward and exclaimed, “That was great, man!” While Colbert knew that the people on stage with him, and those in the front row, weren’t laughing, the bulk of the 3,000 people in the room were loving it.