“You’re maybe the best interviewer I’ve ever had the honor of being interviewed by,” Stephen Colbert said to Howard Stern.
The “King of All Media” was the Tuesday night guest on The Late Show, returning to the Ed Sullivan Theater where he’d made so many indelible late-night memories with David Letterman.
Stern was on to promote Howard Stern Comes Again, a new collection of the legendary radio host’s best interviews.
One of Stern’s most frequent—and infamous—guests was none other than President Donald J. Trump, who regularly berated (and rated) famous women, engaged in shouting matches with gossip columnists over women they’d slept with, and admitted that he turned away in disgust as an elderly man was bleeding to death in front of him.
After ceding the floor to Stern for two whole commercial breaks, wherein he opened up about how he got into radio to impress his radio-engineer father, how therapy helped him, and how he pushed the boundaries of the medium, Colbert eventually began grilling him on “Donald.”
“He was maybe one of the best—top five—guests of all-time,” said Stern. “He was wild. And I thought I was wild! He would start assigning numbers to women and evaluating them.” (To be perfectly clear, Stern asked Trump to assign number grades to women and he obliged.)
That drew heavy boos from the crowd. “[He was] a great guest because he would say anything that came into his mind. He was completely unfiltered. He was talking about [how] his daughter was the most attractive woman he’d ever met, and how much he thought she was hot.”
“It was wild,” Stern continued. “He gets into an argument with the Daily News gossip columnist A.J. Benza. They’re fighting about a woman they both had sex with—on the air. It’s crazy stuff.”
Stern eventually opened up about how Trump was begging him to speak on his behalf at the Republican National Convention—an event that ended up featuring speeches by D-list celebrities Scott Baio and Antonio Sabato Jr.
“He was calling me all through the campaign—I don’t mean on the air, off the air…He wanted my endorsement,” said Stern. “So Donald said, ‘Would you please come to the Republican National Convention and speak on my behalf?’ and I said, ‘Oh my god…’”
“I firmly believed that Donald did not want to run for president,” Stern continued. “I remember, the first time he said ‘I might run for president’ he put out his first book, and I know some of the people involved in this, and they said, ‘Pretend like you’re running for president and you’ll sell a lot of books,’ and he did it and it worked. Second book he put out, it was again like four years later, and he said, ‘I might run for president,’ and again he said, oh, I’m selling books and it might sell books. So what happened this time? He’s on The Apprentice, the ratings were going down, and NBC was balking at giving him a raise, so what did he say? I’ll run for president, I’ll get a lot of press. And I really believe that Donald—this was a gimmick to raise up his salary and keep The Apprentice on. And I would bet the farm on that.”