Howard Stern, let’s face it, doesn’t merely perform interviews; he innovates them. Since the start of his career as a radio shock jock till now, one of the most open communicators in the world, Stern has never hesitated to push the interview guests to disclose themselves in a way that they might not have otherwise. When necessary, he is sharp with his sarcasm; when needed, he shows empathy; and he is never, not even for a second, afraid to stay in the uncomfortable silence. If you are familiar with the typical late-night talk show format—preplanned jokes and well-rehearsed anecdotes—Stern operates on a completely different level. He doesn’t just ask; he hunts, he prods, and on occasions, he might even be a little bit of a gentle touch in helping a celebrity realize a truth they hadn’t considered. These are 15 interviews that not only define the stellar level of communication to which Stern holds but also serve as a reason why he is still the benchmark of celebrity conversations.
15. Lady Gaga
When Lady Gaga dropped by Stern’s studio, it wasn’t promotion—it was therapy. She spoke candidly about her demons in the early days, addiction, and the burden of fame. The peak came when she sat at the piano and sang a stripped-down Edge of Glory that left the room in awe. Few have ever dropped their guard on the air the way Gaga did that day.
14. Courteney Cox & David Arquette
This was not an interview—this was radio’s version of a marriage soap opera. David Arquette stopped by to chat, only to have Courteney Cox suddenly appear and berate him for ruining their troubled relationship. Stern navigated it tactfully but did not hold back, providing listeners with one of the most honest glimpses of a Hollywood split ever heard.
13. Billy Joel
Billy Joel on Stern is sitting in his living room. He mocked his bad times, spoke candidly about booze and dumb decisions, and even played a live rendition of Piano Man. Half confession, half concert, all Billy.
12. Norm Macdonald
Late Norm Macdonald brought his classic dry humor and penchant for disobeying everyone’s instructions. Stern and Macdonald parodied SNL, comedy, and existence with both absurdity and candor. What might have been a silly interview to be funny turned out to be a fairly intelligent, wacky ride of an interview.
11. Charlie Sheen
While Sheen’s “tiger blood” period, the low point of his scandalous behavior, is well-documented, his Stern interview was a portrait of madness. He talked candidly about his addictions, his Hollywood feuds, and his crazy life with the same frenetic passion that rendered him a tabloid sensation. Stern kept up, steering the conversation so that it was enjoyable but also informative—a time capsule of Sheen in full meltdown.
10. Madonna
Madonna is notoriously guarded, but with Stern, she let her hair down. She dished about everything under her pomaded public image: how she grew to fame, her loves, and insecurities. Stern was respectful but insistent, coaxed a rare glimpse of vulnerability out of the pop diva.
9. Paul McCartney
When Paul McCartney dropped by, it wasn’t a typical celebrity interview—it was music history on record. McCartney reflected on the Beatles’ meager beginnings, stardom, and his solo career, all while harmonizing with Stern’s tangible fanboy excitement. It was more like eavesdropping on two buddies joking than an interview.
8. Sia
Famous for having wigs cover her face, Sia arrived on Stern’s show bare-faced. She discussed at great length addiction and mental illness issues, the seedy underbelly of the music business, and topped it off with a spectacular live performance of Diamonds. Stern’s compassion allowed her to be entirely truthful.
7. Steve Martin
Usually a king of one-liners and absurd humor, Steve Martin let Stern step behind the curtain to reveal his darker side. He was open about his strained relationship with his dad and how it affects his work. Combining humor and substance made this an interesting and engaging painting of a comedy legend.
6. Robert Downey Jr.
Before Iron Man made him the comeback king of Hollywood, Downey Jr. sat with Stern to give the entire ugly history—drug use, self-destruction, and ultimate redemption. Stern kept the tone loose and intimate so that Downey could be irreverent, introspective, and very human at the same time.
5. Jon Stewart
Jon Stewart’s sit-down interview was a mixture of humor and pain. He spoke freely about his dysfunctional relationship with his dad, the emotional push that created The Daily Show, and his love of satire as a weapon. Stern was just the right mix of seriousness and humor to allow Stewart to explore both his humor and his pain.
4. Artie Lange
Artie Lange’s on-studio interviews with Stern are the stuff of legend—half comedy, half tragedy. He spoke about addiction, destructive behavior, and surviving with brutal candor, never deviating from his signature humor. Since Stern knew him so well, the interviews were hearing relatives bicker with love, hate, and ferocity.
3. Billy Corgan
The lead singer of the Smashing Pumpkins wasn’t interested in the small talk. He dived straight into depression, creativity, and the heavy price of fame. Stern maintained his intensity, and it produced a raw, almost-philosophical conversation that cut much deeper than your average celebrity interview.
2. Conan O’Brien
Stern has reported this was perhaps his favorite, and no wonder. Conan arrived with humor but was also open to being honest about failure, career setbacks, and his fairly public departure from NBC. The two clicked, so it was an hour of belly-laughing but honest candor.
1. Robin Williams
Robin Williams on Stern was lightning in a bottle. He segued from impressions delivered at breakneck speed to moments of appalling vulnerability in discussing addiction and insecurity. Stern was the interviewer with the rare gift of keeping up with Williams’ manic genius and slowing him down long enough to get the man behind the comedy. It was crazy, heartbreaking, and unforgettable.
What makes Howard Stern the greatest living interviewer isn’t for shock’s sake—it’s trust. He can push but not break, challenge without alienating. It’s Lady Gaga opening up, Madonna dropping her guard, or Robin Williams mixing humor and despair. Stern pieces those interviews raw, raw, and profoundly human. That’s why, year after year, everybody still craves the Howard Stern treatment.