Arguably the biggest radio legend ever, Howard Stern’s hatred of being predictable and his revolting past have made him rich and famous. Howard also has succeeded partically because his celebrity interactions have been hard to predict. For example, nobody would have guessed that Howard would get Donald Trump to talk about his prenup and boast about stealing girlfriends. There were also times that Howard’s interview “hurt” a celebrity, he had a celebrity hold a grudge against him for years, and Dolly Parton threatened to sue him.

One of Howard’s most memorable interviews was a perfect example of how unpredictable the radio host could be. After all, one of Howard’s most uncomfortable celebrity interviews ever also managed to be one of his best simultaneously.

Howard Stern’s Stephen Rannazzisi Interview Was Incredibly Uncomfortable And Compelling

A successful comedian, Stephen Rannazzisi went on to star in the popular sitcom The League between 2009 and 2015. Then, as the last season of the sitcom was airing, Stephen became embroiled in a truly stunning controversy.

During some interviews, Stephen attributed his decision to become a comedian to a harrowing experience. According to Stephen’s earlier comments, he’d been in the South Tower of the World Trade Center on September 11th, 2001. While talking about that day during those interviews, Stephen gave a first-hand account of how he survived the horrific attack and how that changed his life forever. The only problem with that is, nothing Steve said about surviving the September 11th attack was true. In September 2015, The New York Times published an article exposing Stephen’s lies that included an admission of guilt from the actor.

After Stephen’s lies were exposed to the world, the actor and comedian went on “The Howard Stern Show” to explain himself. Howard interviewing Stephen about his lies was one of the best and most uncomfortable moments of the radio host’s career.

On October 6th, 2015, Howard and Stephen’s 40-minute interview was uploaded on “The Howard Stern Show’s” YouTube channel.

From the start, the interview is both awkward and fascinating to watch. As the conversation begins, Stephen briefly lets out a telling sigh that betrays the pressure he was under as he experienced one of the most high-pressure moments of his life. Obviously acutely aware of what his guest must have been feeling, Howard acknowledges the elephant in the room as he welcomes Stephen.

“I thank you for coming in because I know it ain’t easy. I’m sure you’re nervous. But, I thank you for coming in because I want to understand this whole thing because, you know, it does seem like I can’t wrap my head around it.”

From there, Howard asked Stephen about how his deception was discovered. The way Stephen responded to that question appears to betray that he went on Howard’s show prepared with what he wanted to tell the world.

At first, Stephen told Howard that his deception was revealed by The New York Times. Then, Stephen revealed how he learned his lie had been discovered. “It was just it was a complete out-of-the-blue situation. I got a phone call on a Monday.”

Howard didn’t need to ask Stephen another question to prompt what happened next. At that point, Stephen told Howard that it had been a long time since his deception began, and that his lie wasn’t something he’d spoken about a lot in the intervening years.

“It’s been fourteen years… There were waves of the story. In the beginning, it was sort of something that I said and then I did some podcasts a couple years later. But, since then, no one’s ever talked about it. I was on the show, The League, for for the last six years, and no one ever asked me in an interview about it.”

Given the gravity of Stephen’s deception, many interviewers would want to ask blunt questions and speak with a judgmental tone.

Howard took a different tone, however, as he spoke with empathy while asking Stephen why he told the lie in the first place. At the same time, the reason why this is one of Howard’s best interviews is that he also didn’t let Stephen off the hook.

“Are you aware why you lied about being in the Twin Towers? Because sometimes when you make up a story like this, the easy answer is to say, ‘Well, I did it for some sort of attention or something.’ But, I mean, the real deep why is some there’s gotta be something deeply psychological about this. You want people to love you or or something like that.”

While talking about the motivations for his deception, Stephen stated that he was figuring that out while talking about what he’d done. “I’m becoming more aware as I, you know, as I speak to people.”

As the interview continued, Howard asked Stephen about what he said to his wife about his big lie. While talking about what he told his wife about his deception, Stephen stated that he didn’t intend to lie about being involved with September 11th.

Stephen also explained that before his lie was exposed, he and his wife hoped the world would forget what he claimed. “We’re two people who don’t know what to do. Let’s just let it go away.”

As the interview continued, Stephen revealed that his family had been supportive, including his father, who was a firefighter. Stephen also described how his father pledged to help him make things right. “No matter what you’ve done I will help you. I don’t care if I have to walk you from firehouse to firehouse and you apologize to each one of them, we’ll make it right.”

Throughout the forty-minute interview, Howard got Stephen to speak at length about the deception he’d told and its aftermath. It was a fascinating depiction of human experience and how people feel regret. At the same time, it is uncomfortable to see a man grappling with the reality that the world was talking about his misdeed.

Howard Stern Reflected On His Fascinating Stephen Rannazzisi Interview

In October 2015, after the Stephen Rannazzisi interview, HowardStern.com published a follow-up article. That article briefly touched on how the radio show host reacted to the interview.

Most notably, the article reveals that Howard commented on how he was emotionally affected by interviewing Stephen.

The article went on to reveal that Howard and Robin Quivers debated whether Stephen’s lie was worse than someone who deceptively claims to have served in the military. Ultimately, Howard remarked on how he felt about the debate and what Stephen had done.

Finally, the article revealed that after Stephen left the studio, Howard let his listeners call in. Those listeners stated their belief that Stephen needed to continue facing what he’d done.