HOWARD STERN SAIDSOMETHING AWFULABOUT LETTERMAN’S WIFE.THEN HE PAINTED HERA PICTURE TO APOLOGIZE.

The full story of Howard Stern and David Letterman — two reclusive giants of American media who should have been close friends, weren’t, almost destroyed what they had, and then slowly, carefully, put it back together. With a painting.
David Letterman once said, about his friendship with Howard Stern: “I only talk to him about once a year. That’s plenty. And the last time it was a mistake.”

That quote is the whole relationship in three sentences. The fondness. The distance. The absolute certainty that proximity will inevitably produce some kind of damage. David Letterman and Howard Stern are two of the most reclusive, idiosyncratic, control-obsessed men in the history of American broadcasting. They should have been best friends. Instead they spent years feuding, reconciling, feuding again, and eventually arriving at something that resembles — through enormous effort on both sides — genuine mutual respect. It took two formal apologies and a hand-painted watercolor to get there.

I
Two Men Who Should Have Been Friends — And Chose Ratings Instead
Howard Stern has appeared on David Letterman’s show more times than almost any other celebrity. Even during their most difficult years, Letterman kept booking him — because Howard, whatever else he was, was always great television. The chemistry was real. Two men who both hated small talk, both refused to bow to their corporate bosses, both feuded fiercely with Jay Leno, and both found the conventional demands of celebrity life somewhere between suffocating and pointless.

Letterman himself acknowledged it: “I just think we should have been better friends.” Howard, in the most candid version of his own accounting, went further — admitting that he had a habit of taking the private moments of his friendship with Dave and turning them into radio content. A phone call Dave made to Howard in good faith — something personal, something a friend would share — would appear on air the next morning, processed through Howard’s show for laughs and ratings. Dave was not laughing.

II

The Line He Crossed — Letterman’s Wife

Howard has made his career saying things about famous people that famous people didn’t want said. That was the deal. Everyone understood the deal. What crossed the line — the thing that pushed the Stern-Letterman relationship past friction into genuine rupture — was when Howard said something unflattering about Letterman’s girlfriend, Regina Lasko, on his radio show.

The incident involved a photo from the National Enquirer — Regina jogging, hair pulled back, not exactly a flattering moment. Howard, in his standard mode of saying what he thought, said something critical about the photo on air. From Howard’s perspective at the time, it was just the show. From Dave’s perspective, it was his partner. It was personal. And Letterman had to respond to it.

“She is unaccustomed to having people say unpleasant things about her on the radio, and I had to react to that. That’s all that was.”

Howard’s response: “But I was in the middle of trying to be funny?”
Letterman: “Here’s Howard — trying to be funny.”— Exchange between Letterman and Stern on The Late Show, addressing the feud

Letterman was not wrong. And Howard — in the years that followed, once therapy had given him language for what he was doing — was not wrong either. He was trying to be funny. He was also being careless with someone else’s life. Both of those things were true at the same time. That’s the honest accounting of the feud, and Howard eventually gave it.

III

November 22, 2013 — The Late Show Conversation That Showed Everything

Howard’s November 2013 appearance on The Late Show with David Letterman is, by general fan consensus, one of the best late-night interviews in the history of the format. It was raw, uncomfortable, honest, and completely unlike any other conversation either man was having publicly at the time.

They talked about the feud directly. Howard publicly apologized for abusing their friendship. They bonded over their shared reclusiveness — both men genuinely preferring to stay home rather than engage with the social world that their fame had opened to them. They talked about Jay Leno, causing a visible shift in Letterman’s body language when Howard mentioned that Dave had taken a phone call from Leno. Stern was visibly upset. He was, by most accounts, more invested in the Letterman-Leno beef than Letterman himself.

At one point, Letterman accused Howard of having “sold out” — of befriending and socializing with the very celebrities he used to eviscerate. Howard’s response was disarming: “Nobody wants me to have any friends.” The line got a laugh. It also contained something true. The version of Howard Stern who was destroying friendships for ratings was, paradoxically, also the version his audience preferred. The version who went to therapy, painted watercolors, and called Dave once a year was harder to root for in the old way.

IV

2018 — Netflix, “I’m Ashamed,” and the Painting That Said It All

In 2018, Howard appeared on Letterman’s Netflix series My Next Guest Needs No Introduction. The conversation went deeper than the 2013 Late Show session — less performance, more reckoning. Howard said directly that he is “ashamed” of his past behavior with Letterman. He talked about growing up. About therapy. About Beth, and how she had helped him understand what he was doing wrong in his relationships with people.

And then Letterman showed the audience something Howard had brought: a hand-painted watercolor, made by Howard himself, for Regina Lasko. For the woman whose photo Howard had mocked on the radio. The woman Letterman had to defend. A painting — not a press release, not a publicist’s statement, not a generic “I apologize if anyone was offended.” A painting made by hand and given in private, now shown publicly as the most concrete evidence available that Howard Stern meant what he was saying.

The coda came in 2022, when Letterman appeared on Jimmy Kimmel Live and talked about the Howard Stern friendship in the present tense — not as a feud from the past but as an ongoing, if limited, relationship. He told a story about thinking Howard had sent him a painting, texting to say thank you, calling when he got home. Howard’s response: “Oh yeah, I sent that to you by mistake.” Letterman’s conclusion, delivered with perfect deadpan: “I only talk to him about once a year. That’s plenty. And the last time it was a mistake.”

That’s a friendship. Imperfect, intermittent, still capable of producing accidental disasters. But real. After everything — after the feud and the radio mockery and the wife’s photo and the two apologies and the painting — David Letterman and Howard Stern are, against considerable odds, genuinely friends. They just talk once a year. And that, apparently, is enough.