What David Letterman has said about Retirement
2 quotes · 1 episode · May 8, 2026
David Letterman, Late-night host who competed for The Tonight Show, has been quoted on Retirement 2 times in 1 episode of The Bill Simmons Podcast, most recently on May 8, 2026. Each quote below is verbatim and links to the moment it was said.
In their words
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
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
Episodes
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.
David Letterman on other topics
- Late-night television hosting · 2 quotes
- The Comedy Store · 1 quote
- LIV Golf · 1 quote
- NFL overtime rules · 1 quote
- Pardon the Interruption · 1 quote
- Yacht rock · 1 quote