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Howard Stern’s 10 Most Outrageous Public Appearances

The radio host will induct Bon Jovi into the Rock and Roll Hall of Fame this weekend. Judging by history, the King of All Media will steal the show

If you’ve been listening to Howard Stern lately, you’ll know that he is not looking forward to traveling to Cleveland to induct Bon Jovi into the Rock and Roll Hall of Fame on Saturday. He’s spent recent weeks worrying about the quality of his speech, what toiletries he will bring with him on the trip, whether he’ll look ugly on camera and lots, lots more. But anyone who has listened to Stern regularly knows that these rants are part of his process – during his four-decade broadcasting career, he has regularly managed to hit ’em with the Hein whenever he steps out of his broadcasting booth. Here’s a celebration of Stern’s greatest public spectacles. 

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Letterman Meets Miss America (1995)

Stern’s second book, Miss America, suffered no sophomore slump: It quickly shot to the top of the New York Times bestseller list and became the fastest-selling book of 1995. “Ladies and gentleman, we are very near the end of civilization,” said David Letterman while ruminating on those facts. Stern celebrated by showing up to the Late Show in full drag. He accused a visibly uncomfortable Letterman of staring at his chest and ended up kissing the host on the lips – something he would try (and fail) to do again during his last appearance on Letterman 20 years later.

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Howard’s Bowie Birthday Blowout (1998)

Stern has been obsessed with David Bowie for most of his life. But Bowie only appeared on Stern’s show once, showing up at Stern’s 44th birthday party at New York’s Hammerstein Ballroom to sing “Fame,” “Hallo Spaceboy” and “I’m Afraid of Americans,” his biggest hit of the Nineties. “Man, you really truly are a genius and it’s really rare to see you here,” a visibly humbled Stern said. Stern would again pay tribute to Bowie after his death, arranging for Garbage, Greta Van Fleet, Billy Corgan and more to record their favorite Bowie songs. “He was always evolving, he was always on top of things,” Stern said earlier this year. “He was just a great musician and a great songwriter and a great singer. I want to make sure that people remember David Bowie.”

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The Farewell Rally (2005)

When Stern announced he was moving from FM radio to Sirius Satellite Radio in 2004 to escape government regulations, nobody knew if fans were going to pay $12 a month to stay with him. Stern decided to say goodbye to his terrestrial listeners in a big way, inviting thousands to midtown Manhattan on the freezing cold morning of December 16th, 2005, for a huge public rally. “I am erect,” he said, looking out at the audience. He went on to reflect on his hard road to becoming the King of All Media – getting fired, suspended and fined millions for obscenity. “But we stood our ground,” Stern said, thanking his massive audience for sticking with him. “Clear Channel doesn’t have live disc jockeys anymore. I am leaving terrestrial FM radio for a different kind of airwaves so we can once again be free to do this broadcast the way I intend to do it. I will not bow down. I am the last of a dying breed … there will never be another radio show like this. There will never be another audience like this.” 

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Howard Enters the “No Spin Zone” (2008)

After a year at Sirius, Stern had helped the company rocket from 600,000 subscribers to 3.1 million. He appeared on Fox’s O’Reilly Factor to continue to spread the word about his new station. But instead receiving of a warm welcome from host Bill O’Reilly, Stern got pure hostility. O’Reilly said Stern “can’t be serious” for making a reported $500 million. “Listen to you – you are so jealous,” Stern said. “That’s why you sell so many tchotchkes at the end of your show.” Stern even took credit for O’Reilly’s rise: “My show was revolutionary – groundbreaking. There were no Bill O’Reilly’s even, who gave their opinion.”

O’Reilly wasn’t having any of it. He used the third segment of the appearance to paint Stern as an elitist who had lost touch with his working class audience and hung out with “pinhead movie stars.” “You have a house in the Hamptons and you go to Nobu. What’s that all about? I don’t do that,” O’Reilly said. Stern shot back, “Sure you do, you’re gonna paint yourself as some bum?”

Ten years after that appearance, nobody has relished O’Reilly’s oust from Fox News more than Stern. He still often plays clips of O’Reilly’s new podcast, picking them apart line by line. “I guess I’m enjoying someone else’s misery,” Stern said. “Bill O’Reilly was so full of himself.”

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The Birthday Show (2014)

Stern
staged his first public birthday bash in years in 2014 to mark his 60th. It felt like a victory lap; by this point, Stern had
buried old beefs, stopped waging public war with the FCC, and Robin Quivers had
beat cancer. The guest list at New York’s Hammerstein Ballroom included Robert Downey Jr., and brought together late-night rivals Jimmy Kimmel, Jimmy Fallon and David Letterman. But nobody tore the house down more than Joan
Rivers. In one of her last public appearances, she and comedian Jeff Ross roasted Stern and Quivers. In
addition to jokes about Stern’s face, they also took aim at his second marriage to model Beth Ostrosky Stern. “Everywhere Howard goes, he
keeps a picture of Beth in his wallet,” Ross said. “Everywhere Beth
goes she keeps a picture of Howard’s wallet.” Rivers told Stern, “The two of you
are terrific together. I don’t wanna hear about the age difference. … No matter how old you live to before you die, she’ll
still have 30 more years to enjoy the money.” 

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The Final Letterman Appearance (2015)

After Letterman announced his retirement, Stern fretted about his final appearance on the Late Show for weeks. But the appearance was a huge hit, full of greatest hits from past appearances; Stern called out Paul Shaffer of being “baked” and accused Letterman of having checked out years ago. Stern had no idea Letterman would keep him on the couch for the night’s second guest Don Rickles’ final appearance on the Late Show. The result was a Mount Rushmore of comedy, with Stern appearing humbled next to one of his biggest comedy heroes. Rickles skewered Stern’s “trick-or-treat hairdo” before praising him: “You are young, bright, terrific and I swear you are dynamite for the people. God bless you.” Letterman looked confused. “What the hell was that? Good God.”

As Stern predicted, Letterman’s retirement didn’t
last long. And the two aren’t done teaming up; Stern just taped a long interview for
Letterman’s Netflix series My Next Guest
Needs No Introduction

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