Podcast Summary: The Late Show Pod Show with Stephen Colbert

Episode: Intro Rewind: Cole Escola (Extended)

Date: August 28, 2025

Overview

This episode of The Late Show Pod Show features an extended intro with Stephen Colbert, Becca, and Broadway star & comedian Cole Escola. The discussion weaves through quintessential New York experiences, backstage tales, and culminates in an insightful and hilarious interview with Cole about their hit Broadway show, "O Mary." The episode is rich with New York lore, theater anecdotes, and Escola’s witty, offbeat persona.

Key Discussion Points & Insights

New York City Construction and Broadway Life

[04:31-08:14]

• Stephen and Becca discuss the omnipresence of construction noise in New York, particularly around Broadway.

  • Colbert recounts the constant battle with noise during his TV show years, including dynamite blasts during the Colbert Report era.
  • "I've never done a television show in New York that is not across the street from a construction site." – Stephen Colbert [06:30]

• They joke about the mysterious "Daily Bang" heard in their office, theorizing which staffer might be responsible.

Broadway "Tip to Tip" Walk

[09:35-12:20]

• Becca shares her plan to walk "tip to tip" up Broadway, from Battery Park to possibly Sleepy Hollow, discussing the quirks and urban bathroom needs.
  • Stephen gives recommendations: Lincoln Center, Zabar's, Citarella, and the Apple Store.
  • Entertaining side discussion about the now-defunct "Sit or Squat" app for public bathrooms.

Strangers with Candy & Comedy Lineage

[12:22-15:56]

• Stephen and Becca reminisce about Strangers with Candy, including its cult fandom, the show's twisted humor, and how it serves as a barometer for identifying alt-comedians.
  • Colbert: "If they're like, one eyebrow was shaved off, we would think, 'That's Strangers.'" [14:42]
  • Becca notes that the show is now available on Paramount+, and Stephen expresses surprise and amusement.

Interview: Cole Escola

[15:56-24:29]

On "O Mary" and Playing Mary Todd Lincoln

[17:06-20:55]

• Stephen: Outlines the surprising success of Escola's play "O Mary," which transferred from off-Broadway to a blockbuster Broadway run, extended five times.
• Cole:
  • Describes "O Mary" as: "A play about Mary Todd Lincoln played by me... She's an alcoholic wannabe cabaret star inspired by someone very close to me."
  • Reflects on sitting on the idea since 2009, and the initial trepidation of not wanting to “ruin” a cherished concept by writing it down.
    • "I was so scared that once I got it on paper, I would be faced with my own mediocrity." – Cole Escola [19:14]
  • On sharing the idea with others: "I was waiting for someone to be like, you have to write this right now... but because no one did that, [I thought] guess it's a bad idea and I'll never write it. But luckily, I loved it enough that I wouldn't leave it alone." [19:37]

Seeing Others Portray "Mary"

• Cole describes the joy of seeing performers like Betty Gilpin and Titus Burgess take on the role:
  • "To have two of my favorite performers in the world just enthusiastically take over this role and love it like it was their own… It was amazing." [20:30]
• Stephen (mockingly): "God, people hate you."
  • Cole: "These people hate me." (playful banter) [20:55]

On Fame, Taking Breaks, and Future Roles

• Cole jokes about needing to take a break from the spotlight, and expresses a strong desire to play "a straight guy."
• Leads into a comedic “straight guy” performance challenge:
  • Cole: "The key is you have to keep in your mind, enunciating is gay... straight guy's number one fear is being understood." [22:00-22:44]
  • Demonstrates the character with lines like: "Do you know eggs are actually bad for you?" and "What kind of truck is that?"

Notable Quotes from the Segment

• Stephen: "I don't know if I can convincingly play straight at this point, Stephen."
  • Cole: "I don't know that you can either." [23:05]
• On acting differences:
  • Cole (as mean gay): "Did you know eggs are actually bad for you?"
  • Stephen: "Ow. I feel like I just lost an argument I wasn't having." [23:52-23:55]
• Cole: "I love acting. It's one of my favorite things in the world." [24:15]

Notable Quotes (With Timestamps)

• Stephen Colbert [06:30]:
  "I've never done a television show in New York that is not across the street from a construction site."
• Cole Escola [19:14]:
  "I was so scared that once I got it on paper, I would be faced with my own mediocrity."
• Stephen Colbert [14:42]:
  "If they're like, one eyebrow was shaved off, we would think, 'That's Strangers.'"
• Cole Escola [22:00]:
  "The key is you have to keep in your mind, enunciating is gay. Straight guy's number one fear is being understood."
• Stephen Colbert [23:52]:
  “Ow. I feel like I just lost an argument I wasn't having.”

Timestamps for Important Segments

| Timestamp | Segment Description | |--------------|-----------------------------------------------| | 04:31-08:14 | New York construction anecdotes | | 09:35-12:20 | Becca’s “tip to tip” Broadway walk | | 12:22-15:56 | Strangers with Candy retrospective | | 15:56-20:55 | Cole Escola’s journey with “O Mary” | | 21:04-23:55 | Cole’s comedic “straight guy” performance | | 24:15-24:29 | Cole on their love of acting; sign-off |

Tone & Atmosphere

The episode balances intellectual curiosity, classic New York grittiness, and comedic absurdity. Stephen and Becca’s banter, Colbert’s quick-witted tangents, and Cole Escola’s dry, slightly surreal humor create an irreverent and intimate listening experience.

Memorable Moments

• The detailed riff on construction noise, and the "Daily Bang" mystery [08:00]
• Stephen and Becca’s “Strangers with Candy” fan radar [14:42]
• Escola’s self-deprecating take on procrastination and imposter syndrome in creating "O Mary" [19:14]
• The “straight guy off” between Cole and Stephen, with Escola’s comedic acting insights [22:00-23:55]

Conclusion

This playful, meandering episode offers fans of late night, theater, and alternative comedy a rich slice of backstage life on Broadway and TV, capped by Cole Escola's singular, boundary-poking approach to humor and performance. It’s an ideal listen for those craving quick wit, deep dives into the creative process, and authentic New York energy.

For anyone interested in catching "O Mary," find it at the Lyceum Theater on Broadway. For more about Cole Escola and The Late Show, check out their online platforms.