The Tonight Show host Jimmy Fallon surprised fans—and perhaps even himself—when he publicly admitted envy over Howard Stern’s signature long-form interviews. The unexpected confession came during a live taping of the SmartLess podcast in Amagansett, New York, where Fallon was sitting in the audience among stars like Bradley Cooper, Jon Hamm, and Shawn Levy.

The night’s main guest was Stern himself, who joined SmartLess hosts Will Arnett, Jason Bateman, and Sean Hayes on stage for a candid conversation about radio, celebrity culture, and the evolution of interviews in the modern media landscape. When the topic of television’s time constraints came up, Stern pointed to Fallon.

“When Jimmy Fallon does an interview, he can’t do an hour interview because he’s dealing with televisions coming on and off,” Stern noted. “It’s not his fault. It’s just the format.”

That’s when Hayes turned to Fallon and asked directly: Had he ever wanted to do deeper, longer interviews?

Fallon didn’t hesitate.

“You can’t do it,” he said. “I wish I could do a longer interview with certain guests. I do wish I could get into it and talk for an hour. I’m jealous when I listen to Howard. I love it—because when it gets going, it’s great.”

A Moment of Vulnerability in a Room Full of Legends

Fallon’s admission landed with weight, not just because of who said it, but where it was said. The SmartLess podcast—which recently inked a reported $100 million deal with SiriusXM—is known for its irreverent humor and emotional honesty. This wasn’t just another industry mixer. This was a gathering of media powerhouses, many of whom have either shaped or are reshaping the future of interview-driven content.

Stern, now a staple at SiriusXM, has long been lauded for his ability to conduct raw, extended interviews that offer rare glimpses into the minds and emotions of celebrities. Fallon, by contrast, is bound by the 44-minute format of network TV, where segments are chopped for pacing, and where commercial breaks dictate timing more than chemistry.

“Network late-night has always been about rhythm,” said media critic Dana Walton. “But what Jimmy admitted to is that sometimes, the rhythm gets in the way of real connection.”

Johnny Carson Did It. Why Can’t Fallon?

During the conversation, Hayes brought up The Tonight Show’s legendary predecessor, Johnny Carson, who often conducted wide-ranging interviews that could span an entire show.

Fallon acknowledged the difference.

“I love Johnny. He could sit and talk. He could go deep,” Fallon said. “But the landscape now—it’s just not built for that.”

Indeed, in the streaming and digital era, attention spans are both shorter and more fragmented. Network executives are under pressure to keep audiences engaged across increasingly diverse platforms—from linear TV to YouTube, TikTok, and podcast clips. For Fallon, that means balancing monologues, sketches, games, and guest interviews in tight windows.

“He’s running a variety show in the TikTok age,” said media analyst Joel Carlton. “And that means giving you everything in bite-size pieces—even when the conversation deserves more.”

The Podcasting Effect on Celebrity Interviews

Podcasts like SmartLess, Armchair Expert, and The Joe Rogan Experience have transformed the celebrity interview format. Where late-night shows once held a monopoly on entertainment’s most candid moments, podcasts have quietly taken the lead in revealing the personal side of public figures.

Howard Stern’s own evolution—from shock jock to master interviewer—has played a pivotal role in that transformation. In recent years, Stern has hosted some of the most lauded interviews in media, sitting down for uninterrupted hours with everyone from Bruce Springsteen and Hillary Clinton to Conan O’Brien and Lady Gaga.

Fallon’s comments are a clear acknowledgment that he’s watching—and admiring—from a distance.

“When you listen to Howard, it’s like therapy,” Fallon said. “And I’d love to be able to do that.”

Format vs. Freedom: A Growing Tension

Fallon’s frustration mirrors a broader tension in late-night television.

As viewers migrate to on-demand content, traditional late-night shows are grappling with how to stay relevant. Many, including The Tonight Show, have leaned heavily into viral-friendly bits, games, and pre-recorded sketches. But the cost of entertainment at high speed is often depth.

“There’s something special about just talking,” said Arnett during the taping. “We don’t get that on TV anymore.”

Bateman added: “With the long format, you can take your time. You’re not worried about the next segment or hitting the break.”

For Fallon, who cut his teeth on Saturday Night Live and has hosted The Tonight Show since 2014, adapting to the increasingly fractured attention economy has required compromise.

Could Fallon Go Long-Form?

The question now is whether Fallon—or any major late-night host—could realistically transition into deeper, long-form content.

Technically, he’s already dipped into digital: The Tonight Show’s YouTube channel features expanded interviews, behind-the-scenes content, and exclusive music performances. Fallon also has the clout and charisma to command a stand-alone podcast, should he ever want to pursue one.

“There’s a world where Fallon does both,” suggested media strategist Ari Simmons. “Keep the network show, but launch an audio platform where he gets to have those deeper conversations. His audience would follow.”

And with the continued success of SmartLess and other celeb-led podcasts, there’s precedent for dual-career formats in media.

What Fallon’s Comment Reveals About the Future

At its heart, Fallon’s remark wasn’t about jealousy. It was about longing—for a slower pace, a deeper dive, a more human connection.

In a world of viral moments and 90-second interviews, the idea of simply sitting down and talking for an hour feels radical. And that may be the real takeaway from this SmartLess moment: as formats evolve, the hunger for authenticity only grows.

“It was a moment of truth,” said one audience member after the taping. “He wasn’t performing. He was just being real. And ironically, that’s what people want more of in late-night.”

Conclusion: Fallon vs. the Clock

As Jimmy Fallon continues to juggle monologues, games, celebrity guests, and musical numbers on The Tonight Show, his yearning for long-form interviews reveals both a personal itch and a broader media shift.

Whether it leads to a new project, a podcast, or simply a few longer YouTube segments, one thing is clear: even the biggest names in entertainment miss the moments that don’t fit into a four-minute block.

And sometimes, all it takes is an honest comment at a podcast taping to remind us why talking—really talking—still matters.