Since Stephen Colbert was welcoming self-proclaimed king of all media Howard Stern onto Tuesday’s Late Show, it only makes sense that the legendary/infamous radio star got plenty of time to promote his new book, Howard Stern Comes Again. (You get it.) The only booked interview for the night, Stern came out to Jon Batiste and Stay Human’s personalized selection of Elvis Costello’s “Radio, Radio,” slow-danced with Colbert, and then swiped Batiste’s microphone (and irreverently pounded on Batiste’s finely-tuned piano) to sing an improvised ditty about his book, a collection of favorite interviews. So far, so Stern.
Calling his guest “maybe the best interviewer I’ve ever had the honor to be interviewed by” (tied with NPR’s Terry Gross), Colbert did his best to turn the tables, asking Stern, for example, what makes a good interview. Stern pointed to his interview with Colbert on his show, where the two (as recounted in Stern’s book) got into some deep waters in discussing family tragedy, depression, and what drove them both to perform for a living. For people who only know Stern as the guy who talks about his penis (which he did here, briefly), it was illuminating, as Stern and Colbert swapped childhood experiences of learning to be funny and “on” all the time as a way to cheer up their own, similarly depressed moms.
Heady stuff, complete with Stern’s unsurprisingly open endorsement of psychotherapy (even if his therapist constantly has to call Stern on slipping back into avoidance-performance mode), and his thoughtful (if boastful) claim that he could have gotten Hillary Clinton elected if she’d agreed to come on his show in 2016. Stern, copping to attracting an audience of “hardcore dudes” with his mix of scatology, politics, gossip, and outrageousness, yet offered a not-unconvincing analysis of the Electoral College, swing states, and how his media saturation and interview style might just have changed a few outcomes. As to the person who actually did win (by losing by some 3 million tallies in the popular vote), Stern was unsparing both about what a great “wild” interview longtime guest Donald Trump is, and how Trump in no way really wanted to be president.
Telling Colbert that then-candidate Trump called him off-air frequently throughout the campaign, Stern stated emphatically that Trump—as he’d done to pump up book sales over the years—only threw his hairpiece into the ring this time because NBC wanted to cancel The Apprentice. Saying Trump, for whatever else one might think, “knows how to communicate with people,” Stern opined that Trump’s many appearances on Stern’s radio show helped humanize him. (Even if, Stern recounted, Trump did make sport of objectifying women—including daughter Ivanka, whose physical attributes Trump was wont to praise to a degree even noted objectifier Stern found a little creepy.) Agreeing with Colbert that Clinton had been his “white whale” during the campaign, Stern seemed genuinely convinced he could have helped the world avoid the daily nightmare where Donald Trump is president, and genuinely upset he couldn’t.
Not that still-fervent Hillary admirer Stern wasn’t tempted when candidate Trump invited Stern to endorse him at the Republican National Convention. Telling Colbert that he’d pondered how such a heel turn in selling out his “complete beliefs and everything else” might offer him the opportunity to get some revenge upon those who’ve wronged him, Stern explained that, in a Donald Trump administration, the concept of FCC Commissioner Howard Stern was almost too tempting a carrot to pass up. (Avoiding any Democratic endorsements at this stage, Stern did “for selfish reasons” say that Bernie Sanders gets points for being one of the only senators who stood up for Stern and his show when the FCC was trying to drive him off of terrestrial radio in the 1990s.) Stern also posited life as Chief Justice of the Supreme Court under Trump, which, considering this ongoing, flaming clown car pileup of an administration, is just Trump enough to have been on the table.