Mixed Signals from Semafor Media

Episode: Andy Richter on Late Night’s Decline, “Dancing With the Stars,” and New Media
Date: December 12, 2025
Host(s): Max Tani & Ben Smith
Guest: Andy Richter

Episode Overview

This episode features a candid conversation with comedian, actor, and longtime late-night sidekick Andy Richter. The discussion dives into the declining relevance of late-night television, the seismic shifts in Hollywood post-2020, and how new platforms like TikTok and podcasting are changing the business for multi-hyphenate performers. Richter reflects on his decades-spanning career, his time on “Dancing With the Stars,” the evolving media landscape, and what it means to be a "tradesman" in the entertainment industry.

Key Discussion Points & Insights

1. Warming Up Guests: Authentic Conversations

• [03:17] Andy Richter shares his secret to authentic interviews: record as soon as the guest enters, value spontaneous conversation, and avoid formal "commercial vessel" framing.
  • "I very much value authenticity in conversation. So when you tee something up with 'my next guest is...' you're already putting it into a framework that isn't conducive to real human interaction." — Andy Richter (03:38)
• Describes talk show interviews as "gas station food" contrasted with the "fine dining" of real conversations.

2. Being a Tradesman in a Changing Industry

• [05:58] Andy Richter frames his career as that of a tradesman: doing whatever television work arises, from podcasting ("a real thing now") to acting and game shows.
  • "I'm a tradesman and this is my trade. Quite frankly, the industry has been so weird and so sort of fractured that I am just trying to keep irons and fires and keep things going." — Andy Richter (05:59)
• Podcasting fills gaps between acting jobs and has become a vital, enjoyable "side gig" as entertainment work contracts.

3. Hollywood’s Contraction & Post-2020 Changes

• [09:23] Andy Richter addresses underemployment and industry contraction, noting that more veteran performers are turning to podcasting as jobs dry up.
  • "Can I say, fuck, yes. The only solace that I can take from the underemployment...is that I have many, many peers who express the same kind of thing, many of whom are podcasters..." — Andy Richter (09:24)
• Blames strikes, economic shifts, "vertical integration," and a reduced number of content buyers for the dearth of opportunities.

4. "Hot Commodity" Cycles in Showbiz

• [10:48] Andy Richter recalls the early 2000s when leaving "Late Night with Conan O'Brien" briefly made him Hollywood's "shiny new thing," but emphasizes the cyclical, unpredictable nature of fame and opportunity.
  • "I was a shiny new thing when I left the Conan show...I went home with parts in six different movies." — Andy Richter (11:11)

5. The Sidekick Role: Avoiding the Ed McMahon Trap

• [13:53] Richter explains his approach to being Conan O’Brien’s sidekick, striving for comedic and creative equity rather than the "clown/buffoon" model of Ed McMahon.
  • "There was much more of kind of a clown, buffoon kind of role for that kind of person...People would find out like that our audience, they didn't think I was an idiot." — Andy Richter (14:15)
• Details how their dynamic was intentionally more collaborative and less hierarchical.

6. Life After Late Night: Perspective on TV Work

• Reflects on returning to "Conan" after several years away and the adjustment for both he and Conan to reestablish rhythm.
• Appreciated the routine, steady paycheck, and work-life balance the show granted, even though it was less lucrative than sitcom work.
  • "If you're on a popular sitcom for five or six years that goes into syndication, it's an annuity...Whereas what I made as the sidekick on a cable talk show...it isn't the kind of money that piles up..." — Andy Richter (13:19)

7. The Fall of Late Night TV

• [21:01] Richter is blunt: late night as a format "doesn't mean anything" anymore, surviving largely because it's cheap and convenient for networks, but its audience has "diminished."
  • "I think there will always be people that sit at a desk and interview people because it's cheap...The numbers like the Tonight Show or Colbert's big numbers now would have gotten us canceled at 12:30 back in the 90s." — Andy Richter (21:02-22:12)
• Social media, YouTube, and podcasts have overtaken the cultural function late night once served.

8. Dancing With the Stars & TikTok Fame

• [24:16] Participation on “Dancing With the Stars” brought Richter a new generation of fans, especially young women via TikTok, increasing his relevance and industry opportunities.
  • "There's a lot more meetings now than there were back in August...It certainly made me relevant." — Andy Richter (24:16)
• On reportedly lasting longer than expected: owns his lack of dance ability ("I'm the oldest person on the show...I need a hip replacement!”), but attributes success to understanding TV and working with his partner to create daily TikToks.
  • "People would attempt to insult me by saying I was the worst dancer on the show. To which my answer is, no shit. Really? I'm not aware of that. Because...I need a hip replacement." — Andy Richter (25:57)

9. Social Media Comedy as a Craft

• [27:39] TikTok is just another platform for quick, communal comedy, akin to Vine or playground games.
  • "It's just an empty spot. It's what you fill it with. And there's very funny people that are filling it very well, and there's very tacky people who are filling it with tacky stuff." — Andy Richter (27:53)
• Emphasizes that trends and copying aren't the death of creativity but a form of communal participation.

10. Favorite Late Night Guests

• Enjoyed bookings like Will Ferrell, Will Arnett, and especially David Bowie ("got to be friendly with David Bowie, which is just insane").
  • "There was a period where we would have David Bowie on very frequently. And I got to be friendly with David Bowie, which is just insane." — Andy Richter (29:52)

11. What Satisfies Him Creatively?

• Most enjoys acting for its mystery and satisfaction, but also likes directing commercials which feel "like a game show" in their time-pressured logistics.
  • "I like acting. It's the kind of most mysterious one to me. I don't really have technique, I just have experience." — Andy Richter (32:12)
• Views well-made commercials as more rewarding than “shitty, cynical TV.”

12. Game Shows & Jeopardy

• Discusses celebrity Jeopardy experiences – once held highest celebrity score, but lost more recent games to younger, quicker contestants.
  • "Ken Jennings is a good friend of mine...he told me once, sometimes you don't know Final Jeopardy and you're done." — Andy Richter (34:22)
• Finds joy and pride in being part of the lineage of classic American game shows.

Notable Quotes & Memorable Moments

• On Late Night's Decline:
  "Late night doesn't mean anything. I think there will always be people that sit at a desk and interview people because it's cheap....The numbers like the Tonight show or Colbert's big numbers now would have gotten us canceled at 12:30 back in the 90s."
  — Andy Richter (21:01–22:12)

• On Performer Resilience:
  "Many people in Hollywood don't have a 30 year long career....he's a bit ahead of his time in that he's a generalist."
  — Max Tani (38:02, 39:47)

• On Social Media Comedy:
  "It's not just that, like, all creativity has been squeezed out of everyone till there's just no drive to do anything different anymore. It is that there is a communal sort of fun to everybody doing the same thing. And I've likened it to the slide on a playground."
  — Andy Richter (28:25)

Timestamps for Important Segments

• [03:17] — Andy's approach to authentic interviews
• [05:58] — Why Andy keeps "doing it" after 30 years: The tradesman mindset
• [09:23] — The contraction of TV/film jobs and the rise of podcasting as a fallback
• [11:00] — The fleeting nature of being "hot" in Hollywood
• [14:18] — Defining the sidekick role and avoiding the Ed McMahon mold
• [21:01] — The decline and current state of late-night TV
• [24:16] — How “Dancing With the Stars” and TikTok impacted Andy’s career
• [27:39] — TikTok compared to other forms of comedy
• [29:52] — Andy’s favorite late-night guests
• [30:57] — What aspect of entertainment brings him the most satisfaction
• [33:38] — Celebrity Jeopardy and the joy of game shows

Tone & Final Thoughts

The tone is candid, self-deprecating, and lightly comedic, matching Richter’s seasoned and unsentimental perspective on show business. The hosts reflect in their wrap-up on Andy’s resilience, his generalist abilities, and the instructive value of honest, "in the trenches" accounts of the media industry.

For listeners seeking understanding of the entertainment industry's transformation from someone who's lived through much of it, this episode is both insightful and refreshingly direct.