Shocking moments when Letterman meets Stern

Howard Stern

David Letterman should thank his lucky stars for meeting Howard Stern at his “mellowest.” But a sober Howard, who is David’s final guest in his six-episode gabfest on Netflix, “My Next Guest Needs No Introduction,” is still more viewable—and quotable—than most drivel-driven talk show guests on network TV these days.

Before Howard, the TV host’s guests included former US President Barack Obama, George Clooney, Tina Fey, Jay-Z and 20-year-old Nobel Prize laureate Malala Yousafzai. The program’s final episode will be streamed beginning today.

Some of the 64-year-old shock jock’s “revelations” made even the unflappable 71-year-old TV host cringe—like the time when Howard talked to Donald Trump about beautiful women, and the current White House occupant quickly dismissed Angelina Jolie as a mere “seven out of 10.”

As if his declaration wasn’t appalling enough, Donald then added, “You know who’s a great beauty? My daughter Ivanka. Now she’s a 10.”

Howard says he’s a Hillary Clinton supporter, but he has spent more time interviewing Trump than almost everybody in the media because, as the radio host explains, “Donald is the definition of a great guest. No matter what I asked him, he would answer in a sincere and honest way. [I thought] his campaign was more about selling a book or a brand. He’s a friend, but my politics is different.”

To which David interjects with unconcealed concern in his voice: “I worry about it for my 14-year-old [only] son, Harry. I had him when I was 57. When he’s my age, what will we have around us?”

It’s hard to top Howard’s no-holds-barred candor in David’s insightful hourlong show as the Boston University alumnus discusses his childhood, and growing up as “one of only three white kids” in
his high school in a community on Long Island in New York, which is “97 percent black and Puerto Rican.”

Just as riveting are Howard’s views on his personal and professional evolution, and the most controversial moments of his scandal-prone career.

Disclosing how he refused George Clooney’s invitation to visit the superstar’s sprawling villa in Italy, Howard quips, “I’m a homebody. What’ll I do there? If I want to eat an apple, do I need to ask anyone? [Moreover] if I hear more stories about how George helps people, I’ll run right out the door! He’s known for playing practical jokes on his friends, but I want to tell him, ‘You’re good-looking, but you’re not funny.’”

George Clooney

Howard was 14 when Martin Luther King was shot in 1968, at the height of the Civil Rights Movement. He recalls, “The day after [he was killed], my mom’s black friends told her to let me stay home, but she refused. So, I went to school and got the sh*t beaten out of me. Thereafter, we moved to a white neighborhood, which brought me to the realization that the blacks aren’t the only ones who disliked me—even white people did!”

Howard is at his most candid when he talks about his “very liberal” mom. When she asked him what he wanted for his 13th birthday, he told her he wanted a subscription for Playboy magazine, but she refused because she said, “Real women don’t look like that!”

His mother is so cool that the shock jock even poked fun at her—on the air! But, Howard knew he crossed the line when he got his mother livid: “She called me crying after I talked about the kind of forbidden sex that a son should never hear his mom get asked about.”

Howard eventually puts even David on the spot: Just as he wraps up talking about his father’s “large” asset, he then turns the tables on the host and says in a conspiratorial tone, “Come on, Dave. Tell [the audience] about the time when you saw your own dad walk out of the shower … (No response from the flabbergasted David.) Ladies and gentlemen, the son went black!”

Howard still rails against society’s hypocrisy, especially when he discloses how his radio show was fined by the FCC (Federal Communications Commision) for featuring a guest who would play the piano with his penis (“It was theater of the mind,” he reasons).

The irreverent TV host, who’s now sporting a long and shaggy beard, and his guest have known each other since 1984—and it shows, especially when it was David’s turn to hold the shock jock accountable for his recklessness and shock tactics.

David Letterman before the shaggy beard

David remembers how Howard “eviscerated” him over an issue the radio personality was displeased about: “To get back at me, you compared my ratings to Jay Leno’s!”

Realizing how hurtful his actions were, Howard later apologized by sending David’s wife a framed painting of a yellow orchid.

Howard turns thoughtful as he shares, “Because of the ratings race, I often found myself saying the most ridiculous things to get people to listen to the show. So, winning the ratings was met not with euphoria, but with relief.

“I have already apologized to a lot of people. I was a young man who was full of rage. My lack of self-esteem disallowed me to respect anyone—even the people I love.

“I went through therapy because of anxiety. I was trying to control a world that was out of control. It isn’t true that words don’t mean anything!”