Jeff Ross has roasted everyone. Frank Sinatra. Muhammad Ali. Pamela Anderson. Justin Bieber. He stood at a podium at the White House Correspondents’ Dinner and made the sitting president laugh. He performed for U.S. troops in combat zones in Iraq and Afghanistan, in conditions that would make most comedians refuse the gig. He is, by any legitimate measure, the most experienced roaster in the history of American comedy — a man who has built an entire career on saying the most uncomfortable possible thing in any given room.
And on June 25, 2026 — the final Howard Stern Show before Howard’s summer break — Jeff Ross sat down, and Howard Stern made him say the thing underneath all of it.
Part I
“I Almost Died Last Year.” — And He Meant It.
Jeff Ross is 59 years old. In the past few years, he has survived two separate bouts with cancer. He has endured alopecia. He has watched three of his closest friends in comedy — Norm Macdonald, Bob Saget, and Gilbert Gottfried — all pass away within a short span of time. Three men who were not just colleagues but the people he actually called when something was wrong. Gone, one after another, in a stretch that would break most people.
He came to The Howard Stern Show to promote his Broadway one-man show, Take a Banana for the Ride — already a hit at the Nederlander Theatre, starring Ross himself in a yellow suit, telling the story of his life, his grief, and what forty years of making people laugh actually cost him. He came with material prepared. He came, in other words, ready to perform.
“I want tonight to be a cathartic experience. I almost died last year.”
— Jeff Ross, opening his Broadway show
Howard, characteristically, did not let him stay in performance mode. The show went somewhere more personal — to the colon cancer diagnosis, to what it felt like to be the guy who jokes about everything suddenly finding himself sitting across from an oncologist who was trying to soften bad news with humor. Ross’s oncologist, reportedly, told him: “Jeff, good news and bad news. The bad news is you’re going to need six months of chemo.” Ross’s response to that — his instinct to find the joke even in that room — tells you everything about how he has survived everything he has survived.
Part II
Norm. Bob. Gilbert. What Happens When the Funny Ones Are Gone.
The heart of both the Broadway show and the Stern conversation is grief — specifically, the particular kind of grief that comes from losing people who were not just friends but co-architects of your entire identity. Jeff Ross became who he is in conversation with Norm Macdonald. He developed his sense of timing alongside Bob Saget. He learned what it meant to commit to a bit, no matter how uncomfortable, by watching Gilbert Gottfried do it for decades.
All three are gone now. And Ross — the man who built his career on never flinching — has spent the years since trying to figure out what you do when the audience you most wanted to impress is no longer there.
On Howard’s show, Ross talked about his legendary roasts — Joan Rivers, Don Rickles, Chris Rock — and the philosophy underneath all of it: that a roast joke, done right, is an act of love. That you only truly roast the people you respect. That the cruelest-sounding jokes come from the deepest affection.— The philosophy Jeff Ross shared with Howard Stern, June 25, 2026
Howard understood this immediately — because it is, in some ways, the same philosophy that drove his own best interviews. The willingness to say the uncomfortable thing not to wound but to get somewhere real. The idea that discomfort, properly deployed, can be the most affectionate thing in the room.
Part III
The Last Show Before Summer — Why This One Lands Differently
There is something fitting about Jeff Ross being the last guest before Howard’s summer break. Of all the people Howard has interviewed over 40 years — presidents, rock stars, Oscar winners — the comedians have always produced the conversations that hit hardest. Because comedians, more than anyone else, have already done the work of converting pain into something shareable. They show up having already processed the worst of it into language.
Jeff Ross showed up on June 25 having processed two cancers, three devastating losses, and a lifetime of making other people comfortable with their own discomfort. And Howard Stern — the man who spent 40 years being the most uncomfortable person in any room — gave him the space to put it all down for a minute.
As a fan — watching this from the outside, as we always do — what stays with you is not the roast stories or the Broadway clips or even the cancer details. What stays is the image of the Roastmaster General, the man who made his whole career out of never flinching, sitting in that studio and telling Howard Stern that he almost didn’t make it. And Howard — for once — not laughing.
