15 Best Howard Stern Interviews, Ranked

Howard Stern has built a reputation as one of the greatest interviewers in media, known for his ability to get celebrities to open up in ways they rarely do elsewhere. His mix of humor, curiosity, and bold questions creates conversations that are raw, revealing, and often unforgettable, drawing in millions of listeners on ‘The Howard Stern Show.’

From musicians to actors to comedians, Stern’s interviews dig into personal stories, insecurities, and life-changing moments, making his show a go-to for fans craving authentic celebrity insights. Here’s a ranked list of the 15 best Howard Stern interviews, counting down from number 15 to the top spot, based on their impact, candor, and entertainment value.

15. Lady Gaga

Lady Gaga’s interviews with Howard Stern stand out for her openness about her struggles and artistry. She shared details about her early career, including battles with addiction and the pressure of fame, which gave listeners a raw look at her journey. Her emotional performance of ‘Edge of Glory’ live in the studio added depth to the conversation.

Gaga’s chemistry with Stern was electric, as she matched his energy with her candid responses. She even discussed her creative process, revealing how personal pain shaped her music, making this a memorable moment for fans of both her and the show.

14. Courteney Cox and Courteney Cox

David Arquette’s interview took an unexpected turn when Courteney Cox showed up unannounced to discuss their failing marriage. The raw, emotional exchange gave listeners a rare glimpse into their personal lives, with both stars being surprisingly open about their struggles.

Stern’s ability to navigate the delicate conversation kept it respectful yet revealing. The spontaneity of Cox’s appearance and the honesty of their discussion made this one of the most gripping moments in the show’s history.

13. Billy Joel

Billy Joel’s interviews with Stern are a masterclass in storytelling, especially when he opened up about his past struggles with alcohol and reckless behavior, like crashing cars into houses. His willingness to dive into tough topics made the conversation relatable and engaging.

Stern’s connection with musicians shone through as Joel discussed his songwriting process and performed live, including a standout ‘Piano Man’ session. The mix of humor, music, and personal reflection cemented this as a fan favorite.

12. Norm Macdonald

Norm Macdonald’s sharp wit and offbeat humor made his Stern Show appearances a hit with listeners. He shared stories from his ‘Saturday Night Live’ days, including his controversial exit, and didn’t shy away from discussing his unique comedic style.

Stern’s admiration for Macdonald’s fearlessness led to a lively back-and-forth, with both trading jokes and insights. The interview’s blend of humor and honesty made it one of the most entertaining in Stern’s catalog.

11. Charlie Sheen

Charlie Sheen’s interview came at the height of his public meltdown, making it a chaotic, headline-grabbing moment. He spoke openly about his drug use, wild lifestyle, and fallout with ‘Two and a Half Men,’ delivering shocking revelations with unfiltered energy.

Stern’s ability to keep up with Sheen’s intensity while probing deeper into his choices created a riveting conversation. It’s a time capsule of a celebrity at a crossroads, raw and unscripted.

10. Madonna

Madonna’s rare Stern Show appearance was a deep dive into her career and personal evolution. She discussed her rise to fame, relationships, and the challenges of staying relevant, offering insights into her relentless drive.

Stern’s respectful yet direct approach got Madonna to open up about her vulnerabilities, a side she rarely shows. The interview’s balance of career talk and personal reflection made it a standout for fans of the pop icon.

9. Paul McCartney

Paul McCartney’s interview was a dream for music fans, as he shared stories from his Beatles days and solo career. He revealed details about his songwriting process and even discussed lesser-known moments, like his early struggles with fame.

Stern’s genuine fandom and thoughtful questions brought out McCartney’s warmth and humor. The conversation felt like a casual chat between friends, making it a must-listen for Beatles enthusiasts.

8. Sia

Sia’s interview was a powerful mix of music and emotion, with her live performance of ‘Diamonds’ stealing the show. She opened up about her struggles with mental health and the music industry, giving listeners a raw look at her creative process.

Stern’s empathetic approach helped Sia feel safe sharing deeply personal stories. The combination of her vulnerability and musical talent made this one of Stern’s most moving interviews.

7. Steve Martin

Steve Martin’s conversation with Stern was surprisingly introspective, focusing on his strained relationship with his father. Stern’s probing questions led Martin to reflect on how his father’s failed showbiz dreams shaped their dynamic.

The interview’s emotional depth, paired with Martin’s dry humor, created a unique balance. Stern’s ability to guide the comedian through such personal territory made this a standout moment.

6. Robert Downey Jr.

Robert Downey Jr.’s interview was a rollercoaster of humor and honesty, as he discussed his journey from addiction to becoming Iron Man. His candid stories about hitting rock bottom and rebuilding his career were both inspiring and gripping.

Stern’s knack for connecting with guests on a human level brought out Downey’s charm and vulnerability. The interview’s mix of laughs and raw emotion made it unforgettable for listeners.

5. Jon Stewart

Jon Stewart’s interview dug into his personal life, including his painful relationship with his father. Stern’s thoughtful questions helped Stewart open up about how that shaped his comedy and worldview.

The conversation also touched on Stewart’s time on ‘The Daily Show’ and his approach to satire. Its emotional depth and insight into Stewart’s motivations made it one of Stern’s best.

4. Artie Lange

Artie Lange’s multiple appearances on the Stern Show were always raw and real, as he shared stories of his comedy career and personal struggles with addiction. His humor and openness made him a fan favorite, even as he faced dark times.

Stern’s bond with Lange, a former show regular, added a layer of intimacy to the interviews. Their dynamic created some of the most heartfelt and chaotic moments in the show’s history.

3. Billy Corgan

Billy Corgan’s interview was a deep dive into his creative process and personal challenges, including his battles with depression. The Smashing Pumpkins frontman was candid about his music and the toll of fame, making for a compelling listen.

Stern’s ability to connect with Corgan’s intensity led to a conversation that was both philosophical and raw. Fans of the band and Stern alike consider this one of his most engaging interviews.

2. Conan O’Brien

Conan O’Brien’s interview is Howard Stern’s personal favorite, and it’s easy to see why. O’Brien opened up about his career, from his ‘Late Night’ struggles to his fallout with NBC, with humor and surprising vulnerability.

Stern’s admiration for O’Brien led to a warm, insightful exchange that felt like two friends catching up. The mix of laughs and deep reflection made this a high point in Stern’s interviewing career.

1. Robin Williams

Robin Williams’ interviews with Stern were electric, blending his manic comedy with moments of raw honesty. He shared stories about his career, addiction struggles, and personal insecurities, all while delivering rapid-fire humor.

Stern’s ability to keep up with Williams’ energy while guiding him to open up made these conversations legendary. Fans still talk about this as the gold standard of Stern’s interviews for its heart and hilarity.

Which Howard Stern interview do you think deserves a spot on this list? Share your favorite in the comments below!