David Letterman
Late-night host who competed for The Tonight Show
David Letterman (Late-night host who competed for The Tonight Show) has appeared as a guest on 1 episode in TMT. Topics they speak about most include Late-night television hosting, Retirement, The Comedy Store.
In their words
Positions and remarks grouped by topic, each with the exact quote and where it was said.
Other remarks
Letterman praises Netflix as an employer, unlike his past bosses.
“They've been nice. They've been friendly. They're pleasant”
The Bill Simmons Podcast: Five NBA Playoff Takes, Plus David Letterman’s First-Ever BS Pod Appearance (We Did It!!!) (May 8, 2026) · Listen from 1:37:53
Letterman questions whether it is appropriate for the NFL to own a stake in ESPN.
“So is that okay? That the single biggest topic of the sports broadcasting owns that outlet? It seems a little dubious”
The Bill Simmons Podcast: Five NBA Playoff Takes, Plus David Letterman’s First-Ever BS Pod Appearance (We Did It!!!) (May 8, 2026) · Listen from 1:40:45
Letterman recalls spending his year out of work after the NBC morning show drinking heavily.
“mostly I was drinking and drinking to excess. And it was, it was a dark year”
The Bill Simmons Podcast: Five NBA Playoff Takes, Plus David Letterman’s First-Ever BS Pod Appearance (We Did It!!!) (May 8, 2026) · Listen from 1:14:14
Late-night television hosting
Letterman recounts personally calling Michael Jordan to ask him back on the show, but Jordan never returned.
“I called him and I flat out asked him, I said, we really would like you to come back”
The Bill Simmons Podcast: Five NBA Playoff Takes, Plus David Letterman’s First-Ever BS Pod Appearance (We Did It!!!) (May 8, 2026) · Listen from 1:29:35
Letterman says he rarely used guest hosts because he feared losing his show if he gave up the chair.
“deadly scared that if I gave up the seat, I'd lose the show”
The Bill Simmons Podcast: Five NBA Playoff Takes, Plus David Letterman’s First-Ever BS Pod Appearance (We Did It!!!) (May 8, 2026) · Listen from 1:05:39
Retirement
Letterman advises people who are productive and happy to keep working rather than retire at a set age.
“So if you're productive and happy, just keep going for God's sakes”
The Bill Simmons Podcast: Five NBA Playoff Takes, Plus David Letterman’s First-Ever BS Pod Appearance (We Did It!!!) (May 8, 2026) · Listen from 47:10
Letterman says the difficulty of ending his show did not sink in until years after he retired.
“So the real difficulty of it didn't set in for about, I don't know, a year or two, three years”
The Bill Simmons Podcast: Five NBA Playoff Takes, Plus David Letterman’s First-Ever BS Pod Appearance (We Did It!!!) (May 8, 2026) · Listen from 43:29
The Comedy Store
Letterman says Jay Leno was the funniest comic in their Comedy Store group.
“When we were working at the comedy store, he was the funniest in the group”
The Bill Simmons Podcast: Five NBA Playoff Takes, Plus David Letterman’s First-Ever BS Pod Appearance (We Did It!!!) (May 8, 2026) · Listen from 1:35:21
LIV Golf
Letterman says he is pleased that LIV Golf appears to be having financial troubles.
“I'm so pleased that the Live Golf Tournament seems to be having financial troubles”
The Bill Simmons Podcast: Five NBA Playoff Takes, Plus David Letterman’s First-Ever BS Pod Appearance (We Did It!!!) (May 8, 2026) · Listen from 1:23:43
NFL overtime rules
Letterman proposes settling tied NFL games with an escalating field-goal kick-off between the two kickers.
“We start the kicker at the 50. He makes it. Then the other kicker opposing team has to duplicate that”
The Bill Simmons Podcast: Five NBA Playoff Takes, Plus David Letterman’s First-Ever BS Pod Appearance (We Did It!!!) (May 8, 2026) · Listen from 1:17:28
Pardon the Interruption
Letterman finds it discouraging when a guest host fills in for one of Pardon the Interruption's two regular hosts.
“Whenever there's a guest host or somebody filling in for one of the two, it's discouraging”
The Bill Simmons Podcast: Five NBA Playoff Takes, Plus David Letterman’s First-Ever BS Pod Appearance (We Did It!!!) (May 8, 2026) · Listen from 1:05:18
Yacht rock
Letterman says a SiriusXM yacht rock host soured him on the genre until Simmons's documentary restored his respect for it.
“I hate that guy and is what poisoned Yacht Rock for me until I saw your documentary”
The Bill Simmons Podcast: Five NBA Playoff Takes, Plus David Letterman’s First-Ever BS Pod Appearance (We Did It!!!) (May 8, 2026) · Listen from 50:13
Appearances
Five NBA Playoff Takes, Plus David Letterman’s First-Ever BS Pod Appearance (We Did It!!!)The Bill Simmons Podcast · May 8, 2026 · 1 h 57 min
Bill Simmons shares NBA second-round playoff takes, then interviews David Letterman about retirement, late-night TV, yacht rock, comedy peers, sports rule ideas and Netflix.
Discussed in
The Best TV Shows of the 21st CenturyThe Daily · Sep 27, 2026 · 57 min
Natalie Kitroeff talks with Times colleagues Gilbert Cruz and James Poniewozik about the New York Times list of the 100 best TV shows of the 21st century.
Mindy KalingGood Hang with Amy Poehler · Jun 30, 2026 · 1 h 2 min
Amy Poehler talks with Mindy Kaling about her path from Dartmouth improv and Matt & Ben to The Office, The Mindy Project, and Not Suitable for Work.
Colbert's Hissy Fit Farewell Tour, Xi's Ominous Comment, and Murdaugh's New Trial, with Glenn Greenwald | Ep. 1318The Megyn Kelly Show · May 15, 2026 · 1 h 43 min
Megyn Kelly and Glenn Greenwald discuss Stephen Colbert's farewell, fame, Kamala Harris, Trump's China summit and Iran war, the Murdaugh retrial, and 'pretendians.'
Ep 13: Strike Force Five Returns to Celebrate Stephen ColbertStrike Force Five · May 13, 2026 · 48 min
Late-night hosts Jimmy Kimmel, Jimmy Fallon, Seth Meyers and John Oliver reunite to celebrate Stephen Colbert during the final week of The Late Show.
#2480 - Arsenio HallThe Joe Rogan Experience · Apr 8, 2026 · 2 h 59 min
Arsenio Hall joins Joe Rogan to discuss stand-up craft, late-night TV history, Prince, the Comedy Store, parenting, politics and his new memoir.
Often appears with
- Bill Simmons · 1 shared episode