Everything That Howard Stern Has Had To Apologize For

Shock jock and TV host Howard Stern rose to fame as the guy who'd say anything on the radio, including jokes about Columbine High School students and racial slurs. There was also the time when, after singer Selena Quintanilla died, he said, "Spanish people have the worst taste in music. They have no depth," per UPI. Basically, the DJ's willingness to skewer anything and everyone was his trademark back in the '90s and 2000s. Maybe that's why so many celebs have loudly expressed their dislike of Stern.

While Stern has stayed mum on the vast majority of his controversial moments, he has actually apologized to a lot of his former targets. During a 2019 interview with The New York Times Magazine, he credited therapy with helping him clean up his act. He even went on a bit of an apology tour while promoting his 2019 book "Howard Stern Comes Again."

Perhaps thanks to his openness about his less than savory past remarks, Stern has evolved into a respected interviewer with a public image pristine enough that he was asked to be a judge on "America's Got Talent." Hillary Clinton even stopped by his studio for a friendly chat in 2019. But let's not canonize him yet — again, there are plenty of appalling actions and remarks that he's never publicly addressed, like Carnie Wilson's claim that he fat-shamed her. 

Here are some examples of Stern reevaluating his past actions and, yes, sometimes saying the words "I'm sorry."

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 said "nasty things" about Letterman's then-girlfriend Regina Lasko on-air, per The Washington Post. "He said some unpleasant things about my wife and just various little things, and I just thought, 'What did I do to this guy?' " Letterman recalled in 2019.

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. "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," he confessed on the latter. "I had betrayed your trust, and I was ashamed. The reality was I loved you, and I really felt strongly about you." Letterman mused to the Post that if Stern was saying sorry to him, there was probably "a pretty long list of people Howard must be apologizing to." The two are seemingly on great terms as of this writing, 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. "I don't anticipate great opinions from her," he said, per Us Weekly. ​​"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. "I think I'm full-on Free Britney," he said on his radio show, per the Los Angeles Times. He even suggested sexism was to blame for the existence of her conservatorship. "If Charlie Sheen is running his own life — Kanye West, is he hurting himself? Is his career imploding? He doesn't have [a conservatorship]," he said, theorizing this is because the rapper is "a man."

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. I asked Gilda Radner if [her husband] Gene Wilder had a big penis." Come on, Stern. The original Willy Wonka's chocolate bar? That was a mental image none of us needed.

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 "fat pig" on his show, per Fox News. 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 brutal" toward her but added, "At some point I realized how much I admired her." He also called her "a 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. "She told him, 'Stop being such an a**hole," O'Donnell recalled. "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 "maybe one of the best top five guests of all time" on the latter's late-night show, adding, "He was wild."

It was on Stern's radio show that Trump confessed to walking in on women in the changing rooms at the Miss Universe pageant, per resurfaced clips published by CNN. He also joked, "As the owner of the pageant, it's your obligation [to sleep with contestants]." Not to be outdone, Stern told Trump that his daughter was a "piece of a**," 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. "I would bet the farm on that," Stern said. 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.

A Twitter user going by the moniker @PGHowie2 shared a resurfaced clip of the sketch, writing, "Remember that time Howard Stern wore blackface and said the N-word a dozen times? I do." The clip 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 apologize per se. But he did admit that his performance was "f***ing crazy" and hard to watch now. "I won't go back and watch those old shows," he said, per CNN. "It's like, who is that guy? But that was my shtick, that's what I did and I own it." He did specify that the whole point was to make fun of Danson for doing blackface, not to celebrate it. But, he added, "Would I go about it the same way now? Probably not."

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.

"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," Stern told the Associated Press. "I would have just said to him, you know, Robin, I want to apologize," he said. "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 "the world's dumbest person," according to ET Canada, and 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. "I thought it was time I say hello," she recalled telling him. "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. "How nice is that?" she said on the show. "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 "so Hollywood" for apologizing to the people he'd mocked in the past, according to The Wrap. "You started like me, being of the people," she said on her show. "But at some point, you sat behind that microphone for too long."

Stern shot back that same day, calling Williams a "jealous b****," a "cow," and worse on his radio show. He also said, "Worry about your husband, not me," alluding to cheating rumors that turned out to be true about her then-spouse Kevin Hunter. But during an interview with The Hollywood Reporter two months later, Stern admitted he had been "at [his] 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, per People. As of this writing, 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 "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. "​​I do love the show," he said, per The Hollywood Reporter, "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. "He said, 'Congrats to her; it's so hard for little fat chicks to get anything going these days,'" Dunham recalled, "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, per Entertainment Weekly, 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. 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 "it was weird when you used to slam me," Sandler told the radio host in 2015, per Us Weekly. "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 "an a**hole," and the two 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." And no matter what Stern thought about the comedian's films in the '90s, he was clearly not speaking for the majority of the movie-going public. His movies are so popular that Sandler is laughing all the way to the bank.

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" that "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 "unique upbringing" in the Long Island suburbs gave him a valuable perspective on race. "If I was going to be truthful on the air and talk about stuff that I knew, race would have to be included," he said.