Howard Stern is a legend in the world of talk radio. In fact, as astonishing as it sounds, he’s been reigning supreme for nearly 50 years now.

During that time, his show has become famous — or infamous — for being one of the raunchiest and most no-holds-barred forms of entertainment there is. In his time, Stern has interviewed everyone from actors and musicians to comedians and porn stars.

In his many years on the air, Stern has been part of some truly wild and unforgettable moments.

Here are just a few of his craziest and most memorable interviews.

1. Hulk Hogan


To this day, the Hulkster personifies professional wrestling. He remains one of the few professional wrestlers whom even non-fans have heard of.

During the ’80s, Hogan was a cultural phenomenon, telling millions of kids everywhere to eat their vitamins and say their prayers. But there’s more to the man than the larger-than-life character he played on TV.

Indeed, when Hogan — real name, Terry Bollea — came on The Howard Stern show, he was remarkably frank and honest about himself. The interview happened right around the time when Hogan was rumored to be having an extramarital affair with Heather Clem. He took the opportunity to bare his soul to the world and give us a great moment.

2. Crystal Hefner


The Howard Stern Show archives are littered with appearances from Playboy Playmates and other porn stars. Naturally, when Hugh Hefner died, his wife Crystal — a former Playmate of the Month herself — was bound to make an appearance.

Stern has an uncanny ability to get people to reveal intimate personal details about themselves, and Crystal Hefner revealed all about her life — especially her sex life — with Playboy’s founder. Indeed, she revealed so much that she later took to Twitter to apologize.

At one point during the interview, she said that Hugh was a “two-second man” — which probably comes as no surprise to anyone, given how elderly Hefner was. Still, it was embarrassing.

3. Jamie Pressley


When celebrities are on “The Howard Stern Show,” it’s usually Stern himself who’s poking fun at them. But when actress Jamie Pressley made an appearance, she made fun of Stern for what she called his “very Jewish” appearance. She tried walking it back by saying that she didn’t mean that in an offensive way, but Stern was not happy.

She was never invited back on the show again.

4. Jenna Jameson


Legendary porn star Jenna Jameson has been on Howard Stern’s show many times. Each time, she has been cheeky, raunchy and extremely flirtatious with the host. Stern, obviously, didn’t mind any of this and would always roll with it.

5. Gary Busey


Gary Busey is well known as a wild man. And so, when he appeared on Howard Stern, he made sure to live up to that reputation. Not only was he screaming at everyone in his usual way, but he got up and started wrestling the people on the set!