Howard Stern has earned a reputation as one of the most outspoken figures in radio history,
with an envelope-pushing career spanning decades.
Here are some of his most painfully uncomfortable interviews ever.
Before he was president, Donald Trump was a frequent guest on Howard Stern's radio show
in the 1990s and 2000s, and every interview contained at least one cringeworthy moment.
In September 2017, the Chicago Tribune unearthed a 1997 clip in which Trump said he could have,
quote, "nailed" Princess Diana.
At the time he made those comments, Princess Diana had recently died in a car accident.
In October 2016, CNN Money pulled together something of a highlight reel of Trump's interviews
with Stern, including a 2004 segment in which Trump agreed with Stern about his daughter
Ivanka's level of attractiveness:
"My daughter is beautiful, Ivanka."
"By the way, your daughter…"
"She's beautiful."
"Can I say this?
A piece of [beep.]"
"Yeah."
And here's Trump talking to Stern about women over 30:
"30 is like a perfect age."
"Absolutely.
She's had enough life experience."
"Until she's 35."
"Too much life experience.
What is it at 35, Howard?
It’s called check-out time."
Jeez.
Actress Emily Blunt is now married to actor John Krasinski but that didn't stop Howard
Stern from prying into her past relationship with singer and songwriter Michael Bublé
when she appeared on his show in 2015.
"You were perfect together."
"I don't know if I was 'perfect' with him."
"Yes you were!"
"But we had a good time!"
Blunt fielded Stern's questions in a straightforward manner, refusing to say anything negative
about Bublé.
So naturally Stern decided to bring up the cheating rumors:
"He was not faithful."
"Well…
I don't know if it was…
I don't know, it's complicated!
I'm going red!"
Aren't we all?
In 1983, Howard Stern had the late, great comedian Gilda Radner on his radio show as
a, quote, "mystery guest."
The gag quickly got off to an uncomfortable start when Radner said:
"It's totally dumb here."
"It's dumb here?"
"And we agree!"
"We're glad you're so impressed!"
It all went downhill from there.
A caller figured out Radner's identity almost immediately, leading Stern to tell Radner:
"You ruined it.
She came here and ruined my show."
"Sorry!"
"Now what the hell do I do with her for the next half hour?"
After pressing an audibly nervous Radner on her personal relationships and sex life, Stern
capped the interview by asking her:
"Did you have fun?"
"No.
It was pretty scary."
"It was scary?"
“Yeah."
In 2006, Stern told Larry King:
"I guess she had heard I was insane.
And she came in and she was very shaky and kept, sort of getting up and she got up quick…"
Stern says that's when Radner evidently
"...hit her head on a speaker."
Insanely awkward stuff.
Howard Stern took a decidedly sexist approach to his 2005 interview with Emma Bunton, otherwise
known as Baby Spice of the Spice Girls.
"How many guys do you figure you've done in your life?"
"Oh.
So.
Do you think I'm going to talk to you about this?"
"So a few?
More than ten?
I have a reason for asking that."
“Why?”
If that didn't make you squirm, there's also this insanity:
"I'm wondering what it takes to get in your pants."
"She's a catch."
"Do you know what I mean?
Is it like a whole courtship, like, for months or...?"
Honestly, the entire segment is a certified cringe-fest from one moment to the next:
"If a guy wants to spank you, would you throw him out of bed?"
"Um."
"I mean in the right situation.
Obviously he's not going to whack you too hard."
"Not too hard."
We're finding it too hard to make it through this interview, so: Next!
In October 2013, an evidently drunk David Arquette called in to The Howard Stern Show
and gave an interview that might generously be described as "candid."
Arquette had been attending a wrap party for his film The Key, and he told Stern:
"I'm wasted."
According to E! News, he proceeded to embark on a half-hour rant, discussing how the video
game Grand Theft Auto V was too violent and that the only game he wanted to win was
"...the game of love."
All this talk led to an extremely uncomfortable speech about Adolf Hitler, in which Arquette
explained:
"This is the most controversial thing I'm going to say.
… Hitler played the game very well.
He did."
Yes, that is indeed controversial.
Also, idiotic.
In 2015, Radar Online reported that a drunk Arquette called in to The Howard Stern Show
yet again, berating Stern for going to dinner with his ex-wife, Courteney Cox.
Stern ended the interview and said he felt like he should never speak to Arquette again,
but they made up in October 2015.
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