Few are better conversationalists than David Letterman. The former Late Show host took the stage on May 5 at The Montalbán Theatre in Hollywood, part of Netflix Is A Joke Fest 2026—the six-day event that spotlights over 500 comedians in venues across Los Angeles. “This Better Be Funny with David Letterman” featured an intimate interview with John Mulaney.
For 33 years, Letterman was the face of late-night television. As he stood front and center at The Montalbán, his face now sporting a full beard, it was obvious that, while things have changed, his innate ability to disarm audiences (and guests) has not.
The audience seemed to be well-acquainted with Letterman’s history. But that didn’t stop him from taking a trip down memory lane. It was 51 years ago that he stood on stage at The Comedy Store in Los Angeles, hoping to get a spot on Carson’s Tonight Show. And while most of us know the timeline of events that followed—including his contentious relationship with network executives—Letterman opened up about some lesser-known moments, reminding the crowd of his humor and heart.
Letterman took us on a trip down memory lane, reminiscing about growing up in Broad Ripple, Indianapolis, flashing some of his childhood pictures across the screen. He recounted his time as a reporter in Los Angeles, highlighting his sardonic sense of humor. He also spoke about his earliest gigs—working with Robin Williams on Mork & Mindy —and later about his bit with Michael Jackson on The Jacksons variety show in the late ‘70s.
Of course, no trip down memory lane would be complete without Paul Shaffer. Letterman’s longtime late-night sidekick/musical director/bandleader joined him on stage for a quick, amusing chat, while an unintentionally hilarious post by Donald Trump on Truth Social was displayed behind them. “Whatever happened to the very highly overrated David Letterman…” read the post. As if being one of the most-nominated people in Emmy history didn’t give that answer away.
Since 2018, the Emmy winner has been doing what he does best in Netflix’s My Next Guest Needs No Introduction with David Letterman. The intimate one-on-ones are the gold standard of interviews, offering deep, personal, and career-focused conversations with the world’s most talked-about people. Over six seasons, interviews include Barack Obama, Howard Stern, Dave Chappelle, Volodymyr Zelenskyy, and Michael B. Jordan.
John Mulaney made an appearance on the show in 2024, so seeing him take the stage with Letterman on Tuesday night almost felt like a reunion of sorts. Just like his Netflix show, the conversation flowed between Mulaney’s projects, banter, and Letterman’s own experiences. The pair, who are good friends in real life, sat down for a catch-up. The audience just happened to be there for the laughs, and occasionally reminded them of something when they were at a loss, like when Letterman was searching for the name of Bob Hope’s wife, and a rolling wave of “Dolores” echoed through the crowd.
One audience member also cheered for more of Mulaney’s Netflix variety talk show, Everybody’s Live with John Mulaney, which is a continuation of Everybody’s in LA. While Letterman joked about the unexpected crowd participation, the way the banter flowed with the audience made it feel as if we had been welcomed into the chat.
Most of the night, however, was just between Letterman and Mulaney. Both at the top of their game, they ping-ponged questions and stories as if they were in the running to take first place in the Olympics. If interviewing were a sport, this night could very well take top prize.
Letterman took Mulaney through his own trip down memory lane. They touched on Mulaney’s time as a writer at SNL (eventually hosting six times, becoming a part of the elite club), his relationship with Lorne Michaels, his unsuccessful semi-autobiographical Fox sitcom Mulaney (ironically turned down by NBC), which really was ahead of its time, and, among other things, his relationship with his wife, Olivia Munn’s, family.
Mulaney and Letterman closed the night, bonding over their love of music, prompting a return of Shaffer, who, joined by a few vocalists, performed Frank Sinatra’s “That’s Life,” and Elvis Presley’s “Suspicious Minds.”
Somewhere between anecdotal humor, masterful storytelling, and honest conversation, it was easy to get swept away. Witnessing, firsthand, two legendary comics come together to unite and just be present is the ultimate experience. So, no, Donald Trump. Letterman is not “highly overrated.” He rates as the best in the game. Always has been. Always will be.
