David Letterman Reunites with Howard Stern for a Candid, Hilarious Interview

No matter the time, place, or occasion, David Letterman is still capable of making the masses laugh. That was certainly the case when he stopped by Wednesday’s episode of “The Howard Stern Show,” reuniting with Howard Stern for another memorable interview.

Letterman reflected on retiring from late-night television, shared insights into his relationships with notable “Late Show” guests, and discussed what fans can expect from his upcoming Netflix series.

Life After Late Night

Retirement and a New Routine

May 2015 marked the end of Letterman’s 33-year run in late-night television when he stepped down as host of CBS’s “Late Show with David Letterman.” He told Howard he assumed he would continue appearing as a guest on other programs.

“When I left the show, I thought, ‘Well, a lot of people will want me on shows.’ No one wanted me on shows,” Letterman said.

Still, he noted he would soon return to late-night with an appearance on Jimmy Kimmel’s ABC talk show.

These days, Letterman enjoys a quieter life, spending time at his home in Montana riding horses, skiing, and fishing. Howard recalled telling MSNBC host Rachel Maddow about being attacked by a swan while fishing with Jimmy Kimmel — a story Letterman couldn’t resist joking about.

“What a fantastic obituary that could have been,” Letterman said with a laugh.

Howard also pointed out Letterman’s now-signature beard.

“I’ll be buried with this,” Letterman said. “Honest to God, I got so tired of shaving every day.”

Family Comes First

A Different Perspective on Life

One of the greatest perks of retirement, Letterman said, is the time he now spends with his family. He admitted he wishes he had started one sooner.

“The biggest mistake I made was delaying having a family,” he said.

His love for his son Harry is clear.

“I just love making him laugh,” Letterman told Howard. “If I can genuinely make the kid spit stuff out his nose, then I feel like I’m a good dad.”

Early Career Pressure and Paranoia

Letterman explained that his intense focus on career success delayed his personal life. Even after landing “Late Night with David Letterman,” the pressure never eased — especially following Johnny Carson.

“I’m following Johnny Carson, and I don’t know what’s going to happen. There’s a million guys lined up to take my job. Every night was life and death,” he said.

Despite admiring Carson, Letterman admitted he was often too nervous to enjoy their interactions.

“I would always be so nervous around Johnny, I really couldn’t enjoy the moment,” he said.

He also shared a humorous — and alarming — story from early in his career involving comedian George Miller, where he unknowingly smoked marijuana laced with PCP.

“I don’t know enough about the active ingredient in marijuana — and is it compatible with animal tranquilizer? Is anything compatible with animal tranquilizer?” he joked.

The ‘Late Show’ Legacy

Guests, Moments, and Memorable Interviews

Although Letterman has no desire to return to late-night television, he admitted he might approach it differently today.

“In many ways, I wish I could start the show over now because I’m a different person. I’m mature, I have a better understanding of the world around me,” he said.

When asked about connections with guests, Letterman offered a pragmatic take.

“Well, of course, this person acts like they’re enjoying talking to me because this person is an actor,” he said. “I just felt like, well, they don’t want me as a friend, and I don’t know that I want them as a friend.”

He recalled memorable moments with guests like Drew Barrymore, whose 1995 appearance became one of the show’s most talked-about interviews.

“How can you not be affected by that?” Letterman said.

Another standout was Joaquin Phoenix’s infamous 2009 interview promoting the mockumentary “I’m Still Here,” directed by Casey Affleck. Contrary to Phoenix’s claims, Letterman said he was in on the bit.

“I knew what he was doing ahead of time,” Letterman said. “I did enjoy it because it was like getting your work in on the heavy bag. It was easy.”

He also reflected on the eccentric brilliance of Andy Kaufman and his on-air rivalry with wrestler Jerry Lawler.

“Gosh, he was peculiar, and you just loved it,” Letterman said.

And of course, Stern himself became a frequent guest over the years.

“The building was full — it was palpable — of the energy of Howard Stern,” Letterman recalled of Stern’s early days at NBC.

A New Chapter: Netflix and Beyond

What’s Next for Letterman

Letterman recently announced a new interview series with Netflix, produced in partnership with RadicalMedia.

He admitted some envy of Jerry Seinfeld’s “Comedians in Cars Getting Coffee.”

“God forbid Jerry can’t do his show… just give it to me,” Letterman joked.

Ultimately, Letterman said his next project reflects what he does best — asking questions.

“One of my big advantages in life is ignorance,” he said. “If you’re ignorant, there’s nothing you can’t ask a person.”

With at least one major guest already lined up — and Stern volunteering himself — Letterman is optimistic about what’s ahead.

“I think it’s going to be great, and it’ll probably be the last thing I do, so I want it to be great,” he said.