David Letterman’s Netflix interview series My Next Guest Needs No Introduction has lived up to its title for five seasons now, with Letterman welcoming everyone from presidents and pop stars to basketball phenoms, comedians, and Oscar-winning actors. Whether he’s interviewing Barack Obama, Billie Eilish, Caitlin Clark, or George Clooney, Letterman has brought the same mix of curiosity and wit that made him one of late night’s most enduring figures.
But for his longtime fans, there’s an added layer of intrigue when Letterman reconnects with people with whom he’s shared the stage and the occasional absurd stunt across decades of television. With Netflix recently renewing the show for its sixth and seventh seasons, now’s the perfect time to imagine a fan’s dream lineup—ten guests whose shared history with Letterman could make for conversations as surprising, funny, and revealing as any he’s had yet.
Yes, some are pipe dreams. But why let reality get in the way of a good lineup?
Michael Keaton
Letterman and Michael Keaton’s easy rapport has always made for fun television. The two go back to the late 1970s, when they were cast members on Mary Tyler Moore’s short-lived variety series. That they’ve cheered each other on as both rose to the pinnacle of their respective fields makes the idea of a longform reunion all the more appealing, promising laughs, shared memories, and a few stories neither has told before.
Madonna
From her infamous f-bomb laden 1994 Late Show appearance to her more reflective later visits, Madonna and Letterman have always sparked memorable television. With a decades-spanning career still in motion, she’d bring equal parts provocation and perspective to an extended conversation.
Tom Hanks
Tom Hanks may be America’s dad, but his Letterman appearances revealed a sly, self-deprecating wit that matched Dave’s perfectly. With a body of work that now doubles as modern film history, Hanks could give My Next Guest the kind of warm, funny, and deeply human episode that fans would revisit for years.
Oprah Winfrey
Oprah and Letterman’s shared history includes years of tension—culminating in their memorable reconciliation on the Late Show stage in 2005. The two small-screen legends are now in a unique position to compare notes on life away from daily television, and on the personal and professional worlds they’ve built beyond the studio lights.
Cher
Cher’s appearances with Letterman were as unpredictable as they were entertaining, ranging from affectionate sparring to genuine candor. Now in her late 70s and still performing, Cher could bring the mix of showbiz lore, personal honesty, and sharp wit that would make for an unforgettable hour with Dave.
Steve Martin
Whenever Letterman is asked to name his all-time favorite guests, Steve Martin is near the top—and longtime viewers know why. Across his many appearances on Letterman’s shows, the two traded dry barbs, absurd bits, and genuine admiration. But Martin’s talents extend far beyond comedy: he’s an accomplished author, musician, and collector of fine art, and it’s easy to imagine a Next Guest appearance with Letterman at this stage of both their careers being as illuminating as it is entertaining.
Jimmy Kimmel
Jimmy Kimmel has often credited Letterman as his greatest influence, and their on-air encounters have been full of mutual admiration. A Netflix sit-down could bring mentor and disciple together for a candid talk about the craft of hosting, the evolution of late night, and the absurdities of life behind the desk.
Stephen Colbert
All eyes are on Stephen Colbert after CBS announced it was canceling the show Letterman created in 1993 and handed off to Colbert in 2015. Dave made his own opinion on the topic known late last month, calling it “gutless.” A My Next Guest conversation between the two would be must-see TV.
Bob Dylan
Bob Dylan isn’t one to regale talk show hosts with stories of his life and career, but he clearly has a soft spot for Dave, having performed on Letterman’s shows four times. (A 1979 SNL appearance is his only other late-night credit.) If Dylan ever agreed to join My Next Guest, it could yield a singular conversation, with Letterman’s curiosity meeting Dylan’s mystique in ways that might surprise even them.
Jay Leno
The decades-long rivalry between the two late-night titans is etched into television history. Yes, they reunited briefly for a scripted Late Show Super Bowl commercial in 2010, but a sit-down between Jay Leno and David Letterman could offer something we’ve rarely seen: unvarnished candor, shared war stories, and maybe even a few laughs about the whole messy business.
It ain’t Oprah ’til it’s Oprah.
Bob Dylan would be quite a coup.
Has he done Bill Murray yet?
On his Netflix show? Because I came THIS CLOSE in responding that Bill Murray was Letterman’s first guest on Late Night!