Five NBA Playoff Takes, Plus David Letterman’s First-Ever BS Pod Appearance (We Did It!!!)

Episode of 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.

Summary

In the first segment, Bill Simmons offered solo observations on the second round of the 2026 NBA playoffs. He argued that the Oklahoma City Thunder's depth made them too strong for a Luka Dončić-less Los Angeles Lakers team and predicted a sweep. He called the James Harden trade a disaster for Cleveland so far and questioned whether Evan Mobley had plateaued. He also predicted Detroit and New York would advance. He criticized the NBA's slow replay review and revisited the Boston Celtics' first-round collapse. Listener mail covered athletes who won him over, lottery karma and Giannis Antetokounmpo trade scenarios, including Dallas. He also discussed Boston's sports-radio turmoil and the Mike Vrabel–Dianna Russini story.

In the second segment, David Letterman made his first appearance on the podcast. He said the difficulty of retiring did not hit him for about two years and encouraged productive people to keep working. He recalled Johnny Carson's abrupt disappearance after retirement and his own 1970s years in Los Angeles at the Comedy Store and as a sitcom writer. He said a SiriusXM host had soured him on yacht rock until he saw Simmons's documentary. He named Pardon the Interruption as nearly the only TV he still watches.

The two discussed the uncertain future of late-night television and fame in the internet era. Letterman described the year after his NBC morning show was canceled as a dark period of heavy drinking. He pitched a kicking shootout for tied NFL games and other playful rule changes. He also recounted Michael Jordan declining to return to his show and told stories about Jay Leno, George Miller, Norm Macdonald and The Late Shift. Other subjects included a confrontation with Les Moonves and his view that the NFL's stake in ESPN seemed dubious. He praised Netflix as an employer and mentioned plans to attend a Caitlin Clark game in Indianapolis.

Chapters

  1. 0:06

    Intro and Letterman bucket list

    Simmons previews the episode and explains that Letterman was his top dream guest and the inspiration for his mailbag.

  2. 2:34

    Thunder dominate the Lakers

    Simmons breaks down OKC's Game 2 win, praises Ajay Mitchell's trade value and criticizes slow NBA replay reviews.

  3. 10:52

    Cavaliers crumble against Detroit

    Simmons says Cade Cunningham is the series' best player, calls the Harden trade a disaster and questions Evan Mobley's ceiling.

  4. 18:12

    Knicks-Sixers and the Celtics post-mortem

    Simmons expects the Knicks to win quickly and revisits Boston's first-round loss to Philadelphia.

  5. 21:59

    Mailbag: Rocky IV athletes, Spurs-Wolves, lottery and Giannis

    Simmons names athletes who won him over, assesses Spurs-Wolves, adjusts lottery karma rankings and weighs a Giannis-to-Dallas scenario.

  6. 30:24

    Boston sports radio chaos and the Vrabel story

    Simmons compares Boston's current sports turmoil to 1996-97 and reacts to new Vrabel–Russini revelations.

  7. 38:53

    Letterman on fatherhood and retirement

    Letterman discusses his son, his final show and how the difficulty of retiring set in only years later.

  8. 44:19

    Carson, yacht rock and 1970s California

    Letterman recalls Carson's post-retirement disappearance, his change of heart on yacht rock, the Comedy Store years and his early writing jobs.

  9. 1:00:51

    TV today, PTI and the future of late night

    The pair discuss fragmented media, Letterman's love of Pardon the Interruption, late-night hosts and fame in the internet age.

  10. 1:16:08

    Sports rule-change ideas

    Letterman pitches an NFL kicking shootout, quarterbacks who punt and other rule tweaks, and the two discuss golf, F1 and the Masters.

  11. 1:28:03

    Memorable guests, Leno and The Late Shift

    Letterman talks about Michael Jordan, Jay Leno, George Miller, Norm Macdonald and Andy Kaufman, and his dislike of The Late Shift.

  12. 1:37:48

    Netflix, bosses, Indianapolis and Caitlin Clark

    Letterman praises Netflix and recalls clashing with Les Moonves, and they discuss the NFL's ESPN stake, Indiana basketball and Caitlin Clark.

Key points

What was said, by whom, with the exact words. Timestamps jump to the moment.

  • Bill SimmonsCame true

    Simmons predicts the Lakers will be swept by Oklahoma City unless the Thunder have a very poor shooting game.

    “And they're going to get swept unless, okay. See just has a game where they shoot like 30%, which I don't see it happening”

    Listen from 3:49 · Oklahoma City Thunder

  • Bill Simmons

    Simmons argues the NBA should speed up replay reviews and improve its product before expanding.

    “So maybe instead of expansion, maybe try to improve the product before we start adding teams to the product would be my advice”

    Listen from 8:39 · 2026 NBA playoffs

  • Bill Simmons

    Simmons calls Cleveland's James Harden trade a disaster so far, unless it is viewed as a salary dump.

    “So this trade so far has been, um, a disaster unless you just think of it as a salary dump and maybe that's what it was”

    Listen from 12:02 · Cleveland Cavaliers

  • Bill Simmons

    Simmons worries that Evan Mobley has plateaued as a player.

    “The fear is he might be a, you are where you are guy at this point”

    Listen from 15:43 · Cleveland Cavaliers

  • Bill SimmonsDidn’t happen

    Simmons predicts Detroit will beat Cleveland because the Pistons are more physical and have the best player.

    “I think they have the best player, and I think they're going to win this series”

    Listen from 16:58 · 2026 NBA playoffs

  • Bill Simmons

    Simmons argues the Celtics never believed they could lose to Philadelphia and treated the series as an experiment.

    “i don't think they ever thought they were losing to philadelphia i think they used the series as this testing ground”

    Listen from 19:28 · Boston Celtics

  • Bill SimmonsCame true

    Simmons predicts the Knicks will beat the 76ers in five games or fewer.

    “I would just be surprised if this went more than five games”

    Listen from 20:43 · 2026 NBA playoffs

  • Bill Simmons

    Simmons reads Brad Stevens's end-of-season comments as hints toward a Giannis trade.

    “it felt like he was laying a lot of breadcrumbs to Giannis' trade”

    Listen from 29:13 · Giannis Antetokounmpo trade speculation

  • David Letterman

    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”

    Listen from 43:29 · Retirement

  • David Letterman

    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”

    Listen from 47:10 · Retirement

  • David Letterman

    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”

    Listen from 50:13 · Yacht rock

  • David Letterman

    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”

    Listen from 1:05:18 · Pardon the Interruption

  • David Letterman

    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”

    Listen from 1:05:39 · Late-night television hosting

  • David Letterman

    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”

    Listen from 1:14:14

  • David Letterman

    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”

    Listen from 1:17:28 · NFL overtime rules

  • Bill Simmons

    Simmons calls baseball's pitch clock the most successful new rule idea in sports.

    “Baseball's pitch clock is the single most successful new idea I think anyone's come up with”

    Listen from 1:22:07 · Automated ball-strike system

  • David Letterman

    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”

    Listen from 1:23:43 · LIV Golf

  • David Letterman

    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”

    Listen from 1:29:35 · Late-night television hosting

  • David Letterman

    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”

    Listen from 1:35:21 · The Comedy Store

  • Linked moment · 1:37:53Skip to 1:37:53 using a listen link in the info box.

    David Letterman

    Letterman praises Netflix as an employer, unlike his past bosses.

    “They've been nice. They've been friendly. They're pleasant”

    Listen from 1:37:53

  • Bill Simmons

    Simmons says ESPN suspended him for criticizing Roger Goodell and concedes he probably went too far.

    “I was very critical of Roger Goodell and knowing that he was their biggest partner and, you know, in retrospect, probably pushed a little too far”

    Listen from 1:39:16

  • David Letterman

    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”

    Listen from 1:40:45

  • Bill SimmonsPrediction · due Apr 2027

    Simmons predicts the Indiana Pacers will be very good next season with Tyrese Haliburton returning and a new center.

    “They traded for a center. So I think they're going to be really good next year”

    Listen from 1:49:34

People

In the conversation

  • Bill SimmonsSportswriter and founder of The Ringer, host of The Bill Simmons Podcast
  • David LettermanLate-night host who competed for The Tonight Show

Discussed

Topics

More from The Bill Simmons Podcast

From the publisher

The Ringer’s Bill Simmons give his thoughts on various topics around the NBA with Round 2 of the playoffs well underway (3:06). Then, David Letterman comes on to talk about his upbringing, the evolution of talk shows, sports, and much, much more! (38:51). Host: Bill Simmons Guest: David Letterman Producers: Chia Hao Tat and Eduardo Ocampo This episode is sponsored by State Farm®. Like a good neighbor, State Farm is there.® The Ringer is committed to responsible gaming. Please visit https://fanduel.com/playwithaplan to learn more about the resources and helplines Learn more about your ad choices. Visit podcastchoices.com/adchoices

Summary, chapters and key points were generated from the episode transcript on September 28, 2026. Quotes are checked word for word against the transcript.

Categories: Comedy Interviews·Basketball·TV & Film