It’s the morning of Feb. 17, 2015, and Howard Stern is sitting in his dimly lit radio studio in New York City. At this moment, he’s in the midst of his 39th year as a radio host — the only career he’s ever wanted to pursue in his life.
The day’s guest is former Saturday Night Live star and long-time comedian Dan Aykroyd, who happens to be one of Stern’s favorite actors. Before Aykroyd manages to find his seat on the set’s lavender couch, Stern fires a series of penetrating, intimate questions toward his guest.
“Was your early life enjoyable, or was it filled with angst? Did your parents get you as a kid? Did they understand who you were?”
In typical Howard Stern fashion, the therapy session has begun the second Aykroyd steps into the studio. But instead of running from the potentially dangerous inquisitions, Aykroyd bites — and spends the next 60 minutes revealing the most fascinating aspects of his extraordinary life, including dealing with Tourette’s syndrome as a child, the tragic death of his best friend John Belushi, and the drug-crazed years of Saturday Night Live.
There is no one better than Stern at encouraging the most famous people in the world to speak candidly about not just their personal lives, but also their biggest fears, insecurities and regrets. His interview technique is an unusual combination of psychoanalyst and class clown. He routinely disarms his guest by making fun of his own insecurities and shortcomings as a radio host, which encourages the subject to speak freely about themselves. For instance, Stern is notorious for complaining about the size of his penis to his guests. When comedian Kevin Hart joined the show in June of this year, Stern found a way to introduce the recurring subject when he asked Hart about a conversation he had with his father when Hart was a young boy.
Kevin: We (Hart and his father) were driving in the car, and he said ‘Look man, I just want to tell you that everything in life is going to be okay because you got a big dick.’
Howard: Do you have a big dick?
K: I have a huge dick…
H: Mine is pathetic.
In between self-deprecating insults and clever one-liners, Stern takes risks with complicated, yet incredibly fundamental questions, like the ones posed to Aykroyd. He prepares for his interviews up to a week in advance — reading anything and everything about the subject so that he’s prepared to pivot to a serious topic.
Stern also attends therapy sessions on a weekly basis — something he’s quick to admit on his show. Not only do the therapy sessions allow Stern to work out his own personal demons (being fired numerous times as a radio host, his parent’s disapproval of his career at a young age, being rejected by women), they’ve also made him a better interviewer. Stern has an unrivaled knack for connecting dots in a person’s life by psychoanalyzing their words and behavior, which encourages guests to reflect on their lives.
When legendary comedian Steve Martin was on the show in May of 2016, Stern spent several minutes asking about Steve’s tumultuous relationship with his father, Glenn Martin, who Steve called by his first name throughout his life. Like Steve, Glenn aspired to be in show business, but failed.
Howard: Do you think he [Glenn] was jealous of you because he probably had ambitions of being an actor?
Steve: It’s hard to interpret what he was thinking. I believed that my father had ambitions, and children came into his life and those ambitions stopped. He had to go to work as a realtor, and he wasn’t able to pursue his dream.
H: Did your father ever hit you up for an acting part?
S: No. I actually did ask him… he did sort of a walk through in a movie called All of Me.
H: Do you think you gave him that because you were subconsciously aware of his jealousy and maybe you could appease him by giving him a part in the movie, and then he would be complimentary?
S: Wow, you’re good.
These moments—when Stern puts on his therapist hat and coaxes immortal superstars to reflect on the most complicated, human elements of their lives — are what make The Howard Stern Show so different from anything else on radio or TV. Over the course of an hour, he peels back the layers of celebrity and reminds the guest they’re just like everyone else — insecure, lonely, and above all else, flawed.
Here are the five most profound interview moments in the show’s history — when Stern was able to reveal the human elements of his very public guests.
Sia — June 2014
Stern has singer and songwriter Sia on his show to discuss “Diamonds,” which Sia wrote and eventually gave to Rihanna to record. The following interview transcript takes place immediately after Sia performs her rendition of “Diamonds” live on the show.
Howard: Does Rihanna get upset when she hears you sing that because — in a sense — isn’t it like pulling back the curtain? I didn’t know that much about Rihanna, and I thought she wrote that song, and I go “Oh my God this chick is so hot because she’s so deep,” and then I find out you’re the brains behind all that. Then I fell in love with your version of it because you’re the artist. You’re the one who has that vision, and it’s a sad song, isn’t it?
Sia: See I don’t even know. I don’t really analyze my own work.
H: Do you know what it’s about, or you don’t even think about it?
S: I wrote it just for me, and I sang it, and I thought ‘This is great, it sounds like something people would vibe out to on ecstasy in the dance tent at Glastonbury.’ Like I just saw kids with their hands in the air in Ibiza on the beach.
H: I think about your life, and you were so low because of your illness. You almost killed yourself.
H: So I think of you as the diamond in the sky, and that you’re shining bright now.
S: Oh, I’m gonna cry.
H: Right? Isn’t that it?
S: You’re so nice.
H: But you’re shining bright like a diamond now. And it’s so beautiful.
S: You’re so sweet I’m crying.
H: But isn’t that the beauty that you didn’t kill yourself? I mean you almost took your own life and how we would’ve lost out on this diamond in the sky.
S: I can’t talk because I’m crying.
H: That’s good for ratings.
S: Thanks for pulling me back there.
H: I think out of all that misery comes a song like Diamond in the Sky. I don’t think a happy person or a person who hasn’t suffered could write a song like that — with that much emotion.
S: You’re gonna make me cry again.
H: No, but I’m serious. I mean it’s terrible you have to go through that type of pain to write a song, but I think it’s very unique that song. It’s very special.
S: Thank you.
H: And you’re very special. You really are.
S: Thank you.
H: Alright, go ahead and cry.
Bill Murray — October 2014
Legendary actor and comedian Bill Murray talked with Stern at length about his early days at Saturday Night Live and what it’s like to be one of the most famous people on Earth. Near the end of the interview, Murray — who is often reserved — discussed his struggle with loneliness.
Howard: What a life you’ve had. Are you having fun? I don’t mean now, I know this is torture.
Bill: This right here is rollicking (sarcastically).
H: I can’t tell with you. Are you a happy man?
B: Right now, I’m kind of pleased.
H: Has the bane of your existence been relationships with women? Not that you didn’t enjoy them, but… is there something you question in your own life, like why haven’t I found that great love of my life? Do you ever reflect on that?
B: (Takes a deep breath) Well, I think about that. I do think about that. I’m not sure what I’m getting done here. I have kids.
B: I have children that I’m responsible for, and I enjoy that very much. That wouldn’t have happened without women.
H: Are you lonely?
B: I don’t think I’m lonely. It’d be nice to have someone. I mean, it’d be nice to go to some of these things and have a date — to have someone to bring along. But there’s a lot that I’m not doing that I need to do.
H: Therapy, are you referring to?
B: (Laugher) No. Just something like working on yourself or self-development. Becoming more of a person. Not more of a person, but more of myself.
H: More connected to people.
B: Well, more connected to myself. I don’t have a problem connecting with people. My [problem] is connecting with myself.
H: So are you impossible to live with?
B: I don’t think so.
H: So where is the gridlock? You can certainly get women; you’re a very desirable man. I would have random sex with you.
B: I don’t know. I keep thinking maybe it’s something, but I have to do this other thing. If I’m not really committing myself really well to that, then it’s better I don’t have another person. I can’t take on another relationship if I’m not taking care of the things I really need to take care of the most. It’s not a selfish thing; it’s sort of an obligation.
Robin: What has stopped you from getting in touch with you?
B: Well, what stops you Robin?
H: You’re afraid to. That’s what stops me. I get afraid.
B: Exactly. What stops us from looking at ourselves, is that we’re kind of ugly if we look really hard.
H: That’s right.
B: We’re not who we think we are.
H: I think you’ve hit it on the head. I think the hardest thing in the world to do for anybody — I don’t care who you are — is to confront who you are, and to sit there and work on it. Most of us want to run away from that. Even though a lot of good stuff would come out of it, it’s just too Goddamn painful.
Lady Gaga — July 2011
World-famous singer and songwriter Lady Gaga sat down with Stern for the first time in 2011 to discuss her musical career. In typical Stern fashion, the conversation quickly veered toward Lady Gaga’s childhood — when she experimented with drugs and was an outcast. In the following interview excerpt, Stern asks about Lady Gaga’s high school years, and how drugs became an escape from loneliness.
Howard: When you talk about getting high, I mean you were doing some hard-core drugs. You were into coke and you loved ecstasy so much.
Lady Gaga: No, not then. I did later.
H: So you still get high?
L: No, no way.
H: You still smoke weed…
L: Well, come on that’s not…
H: Weed doesn’t make you paranoid?
L: You know I really don’t do it that often, and I’m really honest about it.
H: I like that you’re honest about it.
L: I don’t really like or respect artists that lie about what they do recreationally because it just builds this separation with your fans.
H: But when’s the last time you did coke?
L: Gosh I don’t even remember.
H: Do you think you had a habit? Were you addicted?
L: I was for sure addicted.
H: How did you get off of it?
L: My father kicked my ass. Not really, but you know. He just…
H: He said ‘You’re a mess.’
L: He just called me out. And I love my dad, so when your dad calls you out…
H: Don’t you think you were unhappy? Like I had a period of time when I did a tremendous amount of drugs, and I look back on it now, and I sense that I was lost. I was unhappy.
L: I was so unhappy.
H: What was the source of your unhappiness do you think?
L: I think I was lonely, and there was something about the drug that made me feel like I had a friend.
H: See, I think that of myself. I was very confused, and I was feeling very insecure.
Robin: But it’s also a fitting in thing. A lot of times, you get to fit in because you’re with that group.
L: But see, I didn’t do it with other people.
R: You didn’t?
L: No, I did it alone. I did it all alone in my apartment, and I wrote music. And you know what, I regret every line I ever did. So to any of the little sweethearts listening, don’t touch it. It’s the devil.
Louie CK — April 2015
At least once a year, Louie CK — one of the most respected standup comedians in the world — comes on Stern’s show and reflects on his life. Both Stern and Louie have an obvious affection for one another, and Stern often asks Louie about his own fame.
Howard: This is a weird question, but do you ever get jealous of the young comics in Bushwick who are struggling? Is there some beauty to that?
Louie CK: Fuck yes.
H: There is right?
H: You kind of go, ‘Man they don’t have any pressure on them.’
L: I wish I was them. I really do. That’s the only fantasy I have because everything else I’m doing. I’m fucking playing Madison Square Garden; I’m making a TV show. The only fantasy left is I wish I could go back in time to not knowing how it‘s gonna go and struggling really hard with those dudes in Bushwick.
H: Because you’d think you’d say, ‘You know what it’s horrible.’ Now I have every amenity, I have a beautiful home, this that the other thing. But yet, there’s something sort of elegant and beautiful about being the struggling guy in Bushwick with all the other comics, and everyone’s laying out material, and nobody knows what the future is.
L: That’s right. And you see them all hanging out at the club and they’re shooting the shit, and I walk in and they’re like ‘Ah fuck.’
H: Fuck, here he comes.
L: He’s gonna bump everybody and…
H: You’re the asshole now.
L: Yeah that’s right. I’m the dick.
Robin: Who’s not gonna get to talk tonight?
L: Yeah exactly, here comes this rich douche. And they have no sense that it took me 30 years of suffering.
H: You want to explain to them, ‘Hey excuse me assholes, I waited 30 years to be the asshole.’
Jay-Z — November 2010
In 2010, Jay-Z came on the Howard Stern Show to promote his autobiography, “Decoded.” Jay-Z discusses being abandoned by his own father and how he dealt crack as a young kid to survive.
Howard: You’ve had a weird life. Here’s why I think your life is weird: you’re the type of guy who had this talent, but at the same point you were this crack dealer and hustler.
H: And the reason it’s so weird is when you’re that artistic, and you’ve got so many things going on inside, you could’ve lit a landmine in your life and just gone to jail for a really long time.
J: Absolutely. Or got killed.
H: You shot your brother in the shoulder — point blank pretty much — didn’t you? Because he was fucking around with you?
H: You’re an angry guy…
H: Do you think your anger comes from your father leaving you?
J: Of course.
H: It’s gotta be.
J: It was around that time. My pop left me anywhere between nine and 11. I had a bunch of anger.
H: Did you have a close relationship with him up until that point?
J: Yeah, the closest.
H: Have you ever been in therapy?
H: You seem to be pretty self-realized. Reading in your book, you seem to have a good understanding of the hurt and the pain and everything. You’re able to feel it. Don’t you think that’s something you need to talk to someone about?
J: I’ve spoken to the world about it.
H: But wait a second. Before you become a father yourself, and before you even got married, didn’t you want to sit down with someone and say, ‘Shit, how much is this going to affect my relationship with everyone? How am I going to stay focused on one woman? How am I going to get over the fear that someone’s not going to leave me?’
J: Well, I’ve been dealing with that my entire life. And I’ve been dealing with that through my music. So I deal with that daily.
H: You think that’s enough?
J: Yeah. I’ve got a million therapists.
H: You think that’s really therapy?
J: Yes, of course. Listen to these albums, read those songs. Read the level of — like you said — self-realization. All that therapy is in that music.
Jack Rieger is a freelance writer who covers pop-culture and sports. You can follow him on Twitter @JackRieger.