Howard Stern is an undeniable legend in talk radio. The man appears to have been around virtually forever, with the roots of his radio career going all the way back to the 1970s.

When “The Howard Stern Show” was nationally syndicated on terrestrial radio between 1986 and 2005, it grew to become a pop culture phenomenon. Indeed, the show and its dark humor and frequently raunchy subject matter were an integral part of 1990s American life. Stern’s ability to make his guests comfortable enough to reveal shocking personal details about themselves is nothing short of extraordinary. And the show continues to thrive to this day.

But with so much history behind him, Howard Stern deserves a retrospective. Since his show is known for its wildness and shock value, here are four of Stern’s wildest interview moments.


1. Bree Olson

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Howard Stern is infamous for having porn stars as goes on his show fairly regularly. His interview with former-pro-star-turned-actress Bree Olson turned out to be rather revealing — but not in the way you’d think.

At the time of the interview, Olson was fresh off her breakup with actor Charlie Sheen. The breakup turned out to be devastating for her, and she spoke very candidly with Stern about her pain and heartbreak. The experience was likely cathartic for her, and many listeners who had gone through similarly rough breakups could relate.


2. Jackie Stallone

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Sylvester Stallone is an internationally renowned actor famous for his iconic roles in movies like “Rambo” and “Rocky.”

His mother Jackie, however, became something of a celebrity in her own right when she appeared on “The Howard Stern Show.”

During the interview, she began leveling astonishing accusations against her husband, Frank Stallone Sr. — the most shocking of which was the claim that he once had a relationship with a young woman who was only 19. Things got so heated and crazy that Frank Stallone Sr. actually called in to the show to defend himself. As you can imagine, things erupted at that point.


3. Bill Maher

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Like Stern himself, Bill Maher is no stranger to controversy. Back when he had a show called Politically Incorrect, Maher got himself into trouble shortly after 9/11 for saying that the 9/11 hijackers, whatever else they may have been, were not cowardly.

These comments threw millions into a rage, including Stern himself. When Maher appeared on The Howard Stern Show, the two did nothing but argue and throw insults. They have been at odds ever since.


4. Leah Remini

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People may remember actress Leah Remini for her role in the show “The King of Queens.” More recently, however, she has attracted fame as perhaps the world’s highest-profile critic of the Church of Scientology. Her show “Scientology and the Aftermath” has been seen by millions.

At the time Stern interviewed her, however, she was still a member of the Church. It’s surreal to hear her passionately defending the institution, given what we know now.