Shock jock Howard Stern has had to apologize to a lot of people for what he's said on his radio
show, but which celebrity died before Stern had a chance to make amends? Keep watching to find out.
Back in the '90s, celebrities beefed with their peers to get attention,
much like today's TikTokers. While Howard Stern ruled the radio, he feuded with TV
host David Letterman — even though he considered Letterman a friend off-air.
The two hung out socially and appeared on each other's shows, but things took a sour turn when
Stern went after Letterman's then-girlfriend Regina Lasko on-air. Letterman recalled in 2019:
"He said some unpleasant things about my wife and just various little things,
and I just thought, 'What did I do to this guy?' "
Those remarks were foul enough that Stern apologized publicly — twice. He said sorry
on the "Late Show with David Letterman" in 2013 and on Letterman's Netflix show in 2018.
"Again, I was just a young man full of rage,
and I was angry. I was angry with you, that you were on television, that you had an audience."
Letterman mused to the Post that if Stern was saying sorry to him,
there was probably, quote, "a pretty long list of people Howard must be apologizing to."
The two are seemingly on great terms as of the making of this video,
with Letterman guesting on Stern's SiriusXM show as recently as April 2020.
The 2000s were a tumultuous time for pop star Britney Spears. She became the butt of jokes for
everyone from late-night hosts to her ex Justin Timberlake, so it's no surprise that Howard Stern
was happy to pile on at the time. Back in 2012, when Spears was announced as a new host on "The
X Factor," Stern publicly trashed her during a press conference. He said, according to Us Weekly:
"I don't anticipate great opinions from her.
I'll tune in to see what kind of train wreck she is, absolutely."
But after the documentary "Framing Britney Spears" debuted in 2021,
Stern joined the chorus of celebrities who supported Spears. He said on his radio show:
"I think I'm full-on Free Britney."
He even suggested sexism was to blame for the existence of her conservatorship,
using Kanye as an example to prove his point:
"If Charlie Sheen is running his own life — Kanye West, is he hurting
himself? Is his career imploding? He doesn't have [a conservatorship]."
Stern joins a long list of people who have made public amends to Spears. Everyone from Octavia
Spencer to Perez Hilton is voicing support for the performer. Fans are still waiting for an apology
from Diane Sawyer, though. Stern looks classier than Sawyer? There's a first for everything.
Comedian Gilda Radner made it through the notorious boys' club of "Saturday Night Live"
largely unscathed, but the comedian wasn't laughing after a 1983 interview with Stern. In
fact, she left his studio crying. Even her famous friends, like actor Charles Grodin, were peeved on
her behalf. In a 2002 interview with AV Club, Grodin slammed Stern's comedic style, saying:
"It's just vulgar. I mean, he made my friend Gilda
Radner cry because he asked her so many questions about her sex life."
As recently as 2006, Stern didn't think he'd mishandled the interview
with Radner. On "Larry King Live," he called their talk a "disaster," musing:
"You just never know who's going to be good."
But during Stern's Great Apology Tour of 2019, it finally occurred to him that
maybe the "disaster" was coming from inside the house. He told Page Six:
"I have so many regrets about guests from that time."
Like Howard Stern, Rosie O'Donnell is no stranger to high-profile feuds with her peers.
So it's not surprising that the two hosts went head-to-head throughout the '90s.
Stern bashed O'Donnell on-air for years, and one of his fans even called her a, quote,
"fat pig" on his show. Other Stern fans allegedly dug through her trash as a prank.
But in 2019, Stern told The New York Times Magazine he had privately apologized to the
former "The View" co-host. He admitted he was, quote, "brutal" toward her, and added:
"At some point I realized how much I admired her."
He also called her a, quote,
"fabulous comic," revealing that they've "developed a nice friendship."
And perhaps surprisingly, they have Mia Farrow to thank for that.
She "brokered peace" between them, according to The Hollywood Reporter,
because she appreciated that they were two of the only celebrities willing to call out
her ex-husband, Woody Allen, following his sexual abuse allegations. O'Donnell recalled:
"[Mia] told him, 'Stop being such an asshole. You
and Rosie have more in common than you think.' And really, we do."
O'Donnell is now not just a friend of Stern's, but a repeat guest on his SiriusXM show.
There was a time when Howard Stern considered Donald Trump to be one of
the most entertaining guys around. He told Stephen Colbert that Trump was,
quote, "maybe one of the best top five guests of all time".
It was on Stern's radio show that Trump confessed to walking in on women in the changing rooms at
the Miss Universe pageant, according to resurfaced clips published by CNN. Trump also joked:
"As the owner of the pageant, it's your obligation [to sleep with contestants]."
Not to be outdone, Stern commented on Trump's daughter's beauty,
and the two laughed over their agreement that 35 is, for women, "check-out time."
Despite the fact that they seemingly had so much in common,
Stern refused to endorse or speak on behalf of Trump when he ran for
president. He didn't feel Trump actually wanted to be president, he told Colbert,
and suspected it was a marketing ploy to sell books and increase his NBC salary. Stern said:
"I would bet the farm on that."
He secured an interview with Hillary Clinton in 2019 and was happy to provide her with
a platform for critiquing her former opponent and his former favorite guest.
As we've established, Howard Stern was willing to do pretty much anything for attention in the '90s,
and whether that attention was positive in nature didn't seem to matter.
Perhaps that's how he found himself donning blackface in 1993 for a satire of Ted Danson's
infamous Friars Club performance, where Danson roasted his then-girlfriend Whoopi Goldberg.
The clip recently resurfaced on Twitter, and garnered enough attention that Stern mentioned
it on his SiriusXM show — after he'd insisted on "The View" that he never used the N-word on-air.
When the clip made the rounds, Stern didn't exactly apologize. But he did
admit that his performance was hard to watch now. He said:
"I won't go back and watch those old shows.
It's like, who is that guy? But that was my shtick, that's what I did and I own it."
During Howard Stern's unofficial apology book tour of 2019,
he confessed that one of his greatest regrets was not apologizing to comic actor
Robin Williams before his death. Stern told the Associated Press:
"Instead of him learning that I was a big fan of his, I would just club him
with a question that was ridiculous, you know, like about his nanny. He married
his nanny or something like that. I would have just said to him, you know, Robin,
I want to apologize. I'm such a fan of yours and I was in such a deep hole in my life."
So what had Stern said to Williams that haunted the radio host for so many years?
It all had to do with Williams' alleged affair with his oldest child's nanny Marsha Garces
and his subsequent divorce from his first wife Valerie Velardi, according to the Daily Mail. In
his book "Howard Stern Comes Again," he doesn't go into detail about what he said but admits:
"I was attacking the guy, and he was justifiably furious with me."
Stern claimed that he was planning to call Williams and apologize the week he died,
but he never got the chance.
Howard Stern and Kathie Lee Gifford were at the height of their fame around the same time.
So in true Stern fashion, he decided to start a public war with the daytime TV personality. Stern
once called Gifford, quote, "the world's dumbest person," according to ET Canada. On top of that,
he even cracked jokes about her music career and her husband's alleged cheating. There's a
compilation of his anti-Gifford comments on YouTube that's over two hours long.
Gifford seemed flummoxed by his jabs, especially because she'd never met him.
She talked about their one-sided beef on the "Today" show in 2018, saying that,
when she finally did meet him, she killed him with kindness. She recalled telling him:
"I thought it was time I say hello. I want to wish you the very best with your show."
Around 2012, Gifford got a phone call from Stern.
She said on "Watch What Happens Live with Andy Cohen" that he told her:
"I'm so sorry. You never deserved it. And you've always been so nice.
You just pissed me off because you were just everything I wasn't."
He even sent her a bouquet of roses when she exited "Today" in 2019,
according to Page Six. She said on the show:
"How nice is that? That man hated my guts for 30 years and I prayed for him every single day."
Perhaps the only living media personality who has ruffled as many feathers as Howard Stern is
talk show host and former radio DJ Wendy Williams. Williams was one of the only celebs to cast doubt
on the motivation behind Stern's contrite book tour. In March 2019, she mused that he was, quote,
"so Hollywood" for apologizing to the people he'd mocked in the past. She said on her show:
"You started like me, being of the people. But at some point,
you sat behind that microphone for too long."
Stern shot back that same day, calling her out in more ways than one.
"You'll never be me, Wendy. You'll never be me. You don't have my wit,
and you don't have my talent."
But during an interview with The Hollywood Reporter two months later,
Stern admitted he had been, quote, "at my worst" when he insulted Williams on-air and regretted it.
The pair's feud picked back up again in January 2020 when Stern shaded
Williams for being inducted into the National Radio Hall of Fame before him,
according to People. As of the making of this video, Stern hasn't
publicly apologized for that jab. However, Williams mentioned it on her show, saying:
"Howard, you know what, if you never apologized to me ever in your life, you would still be one
of the most influential people in shaping my career — you and Oprah, that's it."
Lena Dunham broke new ground when she starred in "Girls," the HBO show that she also created,
produced, and directed. She was at the forefront of the body positivity movement,
and people praised her for showing skin on television.
But not everyone was a fan. And Howard Stern, who publicly shamed women like Anna
Nicole Smith and Carnie Wilson for their weight when they stopped by his studio,
made his feelings on Dunham's appearance known. In 2013, he called Dunham, quote,
"a little fat girl who looks like Jonah Hill," according to E!. A few months later,
he backtracked, saying he was a fan of "Girls" and that he wanted to apologize to her. He said:
"​​I do love the show, and it makes me feel bad that she is getting the
impression that I somehow think she's just a talentless little fat chick."
Dunham had a sense of humor about it. When stopping by the "Late Show with
David Letterman," she responded to his remarks. Dunham recalled:
"He said, 'Congrats to her; it's so hard for little fat chicks to get anything going
these days', and it put me in the best mood. I just want my gravestone to say,
'She was a little fat chick, and she got it going.'"
She has since appeared on Stern's SiriusXM show and even discussed her weight with
him, so it's safe to say these two have buried the hatchet.
Adam Sandler may not be the Marlon Brando of our time, but he puts a lot of effort into his work.
"You were nicer to me though. It was not nice what you did to me!"
So when Howard Stern skewered his film career throughout the 1990s and 2000s,
Sandler apparently didn't take it well.
Sandler confessed that he idolized Stern when he was a student at New York University,
so the insults hit him pretty hard. He told Stern on his show:
"It would break my heart because I loved you growing up."
Stern said he knew he'd taken things too far when
the two were on the same flight and Sandler avoided him the whole time.
He admitted that he'd been harsh, and the two subsequently patched things up on the air.
Nowadays, it seems Stern and Sandler have a thriving bromance:
They even sang a Torah blessing together on a 2018 episode of "The Howard Stern Show."
Howard Stern released the books "Private Parts" and "Miss America" at his '90s peak.
The tomes contain more than a few cringe-worthy passages,
at least one of which he says he regrets. Stern wrote in "Miss America":
"Homosexuality seems to be a way for men in our society to avoid
the responsibilities of being an adult male."
However, he told The New York Times Magazine that he never
actually believed that and only wanted to grab people's attention. He added:
"I am only a proponent of gay rights,
gay marriage [...] But if you read my books or listen to my old raps, I sound insane."
Still, when called out in the same interview, he refused to walk back his remarks about Rodney
King. In "Private Parts," he had touched on the protests and riots that occurred
after Los Angeles police officers were caught on camera beating King. He wrote:
"[The LAPD] didn't beat this idiot enough."
He doubled down on his statement when speaking to Rolling Stone in 1994, saying:
"I think Rodney King is a blight on society."
When pressed, he told the Times he didn't feel he'd crossed any lines and that his, quote,
"unique upbringing" in the Long Island suburbs gave him a valuable perspective on race. He said:
"If I was going to be truthful on the air and talk about stuff that I knew,
race would have to be included."
Check out one of our newest videos right here! Plus,
even more Nicki Swift videos about your favorite celebrities are coming soon.
Subscribe to our YouTube channel and hit the bell so you don't miss a single one.