Monday Morning Podcast

Host: Bill Burr
Guest: Carol Leifer
Episode: Comedian Carol Leifer 'How To Write A Funny Speech' | Thursday Afternoon Monday Morning Podcast 8-21-25
Date: August 21, 2025
Theme: Writing and delivering funny, heartfelt speeches for big life events, standup origins, career reflections, and classic Bill Burr takes on sports, relationships, and modern society.

Episode Overview

Bill Burr welcomes legendary New York standup and comedy writer Carol Leifer, discussing her new book, How to Write a Funny Speech (for a wedding, bar mitzvah, graduation, and every other event you didn’t want to go to in the first place). They share horror stories and tips about public speaking, recount their comedic upbringings, riff on standup’s unwritten rules, and touch on everything from AI speechwriting and the state of modern comedy to the ever-relevant pain points of family, parenting, and relationships. Burr is candid, funny, and self-deprecating as ever, with Leifer providing sharp, witty insight throughout.

Key Discussion Points & Insights

Why Write a Funny Speech Book?

Burr’s Public Speaking Jitters: Despite being a pro, Bill admits, “I have avoided these things my whole life. I get afraid of these things.” (01:10)
Leifer’s Motivation: Carol and co-author Rick Mitchell wrote the book because “We'd been to too many events where people get up, they make a speech, and they shit the bed… it's not that hard to give a good speech, to give a funny speech.” (03:21)
Changing Stakes: Unlike pre-smartphone days, she notes, “Now somebody’s recording it. It’s up on the web… it’s on the Internet forever haunting you.” (03:40)

Essential Speechwriting Tips

Keep it Short: “The number one rule... five minutes and under. Because people get up there—” (06:36, Leifer).
Burr: “Can’t do six minutes, okay. This is a late night set.” (06:53)
State Your Relationship: Leifer cautions, “You have to say who you are to the person. Now, regarding heartfelt and funny…” (07:49)
Balance Heart and Humor: Burr shares his workaround: “What I had to do was say two, three nice things and then make a joke.” (08:47)
Self-Deprecation Works: “Self-deprecating is always like… it gives them something to root for.” (10:37, Burr)

The Pain of Watching Bad Speeches

Witnessing Fails: Leifer recounts wedding and graduation speech disasters: “People at the valet parker were talking about it as they were leaving, how bad his speech was.” (04:21)
Interventions: “I helped a friend of mine with her speech because I really couldn't take it.” (12:31, Leifer)
AI Can’t Fix It: They joke about trying AI to write a speech—“Her opening was ‘Good evening, distinguished guests.’ I mean, what is this, a Rotary Club meeting?” (13:08, Leifer)

On Stage—Standup vs. Ceremonial

Imposter Syndrome: On following John Mulaney, Will Ferrell at the Conan event—“If I knew he was going up first, I would have been like, you don't need me… We gotta follow this. This is fucking ridiculous.” (09:21, Burr)
Comedians vs. Civilians: Leifer: “The bar is set very low for a person... people are rooting for you. And I think once people know that about giving a speech, it really can calm the nerves.” (09:53)

Comedy Career Reflections

Standup Origins: Leifer started at Comic Strip Live in NYC (1977), hosted by Jerry Seinfeld: “My audition night at the Comic Strip. Jerry Seinfeld was the emcee, and it was me, Paul Reiser, and Rich Hall, and he put us all through.” (23:34)
Breaking In as a Woman: “As a woman, you must have really had it tough. And it really. I really found it was a big advantage. And that also, the guy comics were so supportive…” (32:32)
Old Rules of Standup: Burr runs through the unwritten rules he grew up with—no facial hair, can't be too good-looking, don't do AIDS jokes, etc.—and questions their value: “It was almost like they were saying, there’s only one kind of music.” (33:38)

The Evolving Comedy Landscape

Cultural Change: They discuss pushback against “the coddle generation” and shifting standards in comedy and parenting (34:09–38:45)
Empathy & Artistry: Burr: “The hardest emotion is empathy... It’s an art form. You can go out and do it however you want to do it.” (38:45)
Censorship & Joke Policing: “There's definitely been, in the last 10 years, this pendulum of... people, including comedians, trying to tell people what you should and shouldn't be able to say... It’s a very slippery slope.” (39:15–39:48)

Memorable Showbiz Anecdotes

Jerry Lewis at Burr’s Graduation: Burr recounts Jerry Lewis doing “Crazy Jerry” at breakfast, then “Telethon Jerry” for the commencement—“It was awesome... I saw the entire gamut of what this guy can do.” (18:30–20:24)
Standup Bomb Stories: Burr tells of being called "Billy Bucks" at a disastrous high school prom gig: “That one kid… just looked at me, just went [shakes head]. Like, why did you ever even think?” (41:58–43:16)
Bomb Aftermath: Leifer recalls bombing at a corporate gig—and overhearing the brutal audience review in the restroom.

Quick Comedy Wisdom

First-Time Standup: Both agree—the first 10–15 times up, “It’s just about having the balls to go up there.” (27:00, Burr & Leifer)
Practicing Material: “Do you practice in front of a mirror?” “Yeah. Oh, I’ve tried it. It doesn’t work, right.” (27:48)
Steven Wright’s Advice: “Do standup every night for three years and not judge yourself. To become a really good standup, you have to just go on and go on and fall in your face and bomb. And that’s what it takes to get good.” (28:11, Leifer relaying Wright’s advice)

On Broadway & Acting

Burr’s Broadway Experience (Glengarry Glen Ross): The unique challenge of reading the Broadway crowd, especially for foreigners, and working with Michael McKean. “The only thing that was really—well, because you’re used to, like... me and the crowd. But with other actors, that’s the addition.” (46:11)
Professionalism and Camaraderie: The cast developed ways to keep the show fresh and fun, even joking about mixing up lines for laughs backstage. (47:44)

Notable Quotes

“I needed this book.” (01:03, Bill Burr)
“People are rooting for you. And I think once people know that about giving a speech, it really can calm the nerves.” (09:53, Carol Leifer)
“Five minutes and under. Even if it’s your own daughter.” (06:49, Carol Leifer)
“Just get up there and say who you are to the person … it becomes like an episode of Dateline.” (07:46, Leifer)
“Self-deprecating is always like… it gives them something to root for.” (10:37, Burr)
“There is a war out there for your brain. And they want your brain flatlined, not thinking.” (14:42, Burr, on AI & social media)
“You gotta do standup every night for three years and not judge yourself. ... fall on your face and bomb. And that’s what it takes to get good.” (28:11, Steven Wright advice via Leifer)
“Do your own thing—don’t listen to other people.” (34:09, Leifer)
“The hardest emotion is empathy.” (38:45, Burr)
“If you want to have a good set … and not torture people you love … you want to see 'life of the party' … [this book] is all-purpose.” (56:58, Burr)
“She [Carol Burnett] literally said, 'Send it.' ... Monday she sent the foreword. I mean, who does that?” (57:59, Leifer)

Timestamps for Key Segments

[00:00–01:10] – Burr’s praise for Leifer, introduction of book and theme
[03:18–04:49] – Why people bomb at important speeches, the horror of bad public remarks
[06:33–07:23] – Rule #1: Five minutes or less, and other key writing tips
[08:47–09:45] – Handling nerves, following superstar acts
[09:53–11:15] – The bar is low for civilians, use nerves for energy, self-deprecation
[12:05–13:41] – Worst speech stories, trying AI to write a speech (with hilarious results)
[14:42–15:36] – Distrust of AI, social media, and the dangers of brain-drain
[23:34–24:41] – Leifer’s early standup days, getting passed by Seinfeld & club politics
[27:00–29:09] – Getting started, Steven Wright’s advice, ignoring naysayers
[33:38–34:09] – Dumb old rules of standup, evolution of comedy
[41:03–43:16] – Standup horror stories: prom gigs, brutal audience feedback
[46:11–48:55] – Burr’s Broadway experience, reading the crowd, working with Michael McKean
[54:05–55:36] – Paying tribute to previous generations, club/circuit history
[57:59–58:24] – Carol Burnett’s generosity, writing the foreword for Leifer
[58:56–59:07] – Where to purchase the book, closing thanks

Tone & Language

The episode retains Bill Burr’s trademark rants—irreverent, blunt, and hilarious—paired with Carol Leifer’s dry wit and industry wisdom. Their rapport is collegial and affectionate, often veering into self-deprecating anecdotes and standup-lore name-drops. The humor is punchy but full of practical advice for anyone dreading a public speech or trying to avoid being “that guy” at a wedding.

Conclusion

This episode is a goldmine for anyone facing the terror of giving a toast or ceremonial speech, packed with practical tips and firsthand stories from two seasoned pros. It’s also a time-capsule of comedy culture, spanning from 1970s NYC standup to today’s shifting standards, enhanced by classic Bill Burr rants on relationships, social media, the Illuminati, and, of course, the Red Sox and Yankees.

Recommended for:

Anyone writing a speech
Standup comedy fans/historians
Fans of candid showbiz stories and sharp, funny conversation

“How to Write a Funny Speech” by Carol Leifer is available everywhere books are sold.

Monday Morning Podcast

Episode Overview

Key Discussion Points & Insights

Why Write a Funny Speech Book?

Burr’s Public Speaking Jitters: Despite being a pro, Bill admits, “I have avoided these things my whole life. I get afraid of these things.” (01:10)
Leifer’s Motivation: Carol and co-author Rick Mitchell wrote the book because “We'd been to too many events where people get up, they make a speech, and they shit the bed… it's not that hard to give a good speech, to give a funny speech.” (03:21)
Changing Stakes: Unlike pre-smartphone days, she notes, “Now somebody’s recording it. It’s up on the web… it’s on the Internet forever haunting you.” (03:40)

Essential Speechwriting Tips

Keep it Short: “The number one rule... five minutes and under. Because people get up there—” (06:36, Leifer).
Burr: “Can’t do six minutes, okay. This is a late night set.” (06:53)
State Your Relationship: Leifer cautions, “You have to say who you are to the person. Now, regarding heartfelt and funny…” (07:49)
Balance Heart and Humor: Burr shares his workaround: “What I had to do was say two, three nice things and then make a joke.” (08:47)
Self-Deprecation Works: “Self-deprecating is always like… it gives them something to root for.” (10:37, Burr)

The Pain of Watching Bad Speeches

Witnessing Fails: Leifer recounts wedding and graduation speech disasters: “People at the valet parker were talking about it as they were leaving, how bad his speech was.” (04:21)
Interventions: “I helped a friend of mine with her speech because I really couldn't take it.” (12:31, Leifer)
AI Can’t Fix It: They joke about trying AI to write a speech—“Her opening was ‘Good evening, distinguished guests.’ I mean, what is this, a Rotary Club meeting?” (13:08, Leifer)

On Stage—Standup vs. Ceremonial

Imposter Syndrome: On following John Mulaney, Will Ferrell at the Conan event—“If I knew he was going up first, I would have been like, you don't need me… We gotta follow this. This is fucking ridiculous.” (09:21, Burr)
Comedians vs. Civilians: Leifer: “The bar is set very low for a person... people are rooting for you. And I think once people know that about giving a speech, it really can calm the nerves.” (09:53)

Comedy Career Reflections

Standup Origins: Leifer started at Comic Strip Live in NYC (1977), hosted by Jerry Seinfeld: “My audition night at the Comic Strip. Jerry Seinfeld was the emcee, and it was me, Paul Reiser, and Rich Hall, and he put us all through.” (23:34)
Breaking In as a Woman: “As a woman, you must have really had it tough. And it really. I really found it was a big advantage. And that also, the guy comics were so supportive…” (32:32)
Old Rules of Standup: Burr runs through the unwritten rules he grew up with—no facial hair, can't be too good-looking, don't do AIDS jokes, etc.—and questions their value: “It was almost like they were saying, there’s only one kind of music.” (33:38)

The Evolving Comedy Landscape

Cultural Change: They discuss pushback against “the coddle generation” and shifting standards in comedy and parenting (34:09–38:45)
Empathy & Artistry: Burr: “The hardest emotion is empathy... It’s an art form. You can go out and do it however you want to do it.” (38:45)
Censorship & Joke Policing: “There's definitely been, in the last 10 years, this pendulum of... people, including comedians, trying to tell people what you should and shouldn't be able to say... It’s a very slippery slope.” (39:15–39:48)

Memorable Showbiz Anecdotes

Jerry Lewis at Burr’s Graduation: Burr recounts Jerry Lewis doing “Crazy Jerry” at breakfast, then “Telethon Jerry” for the commencement—“It was awesome... I saw the entire gamut of what this guy can do.” (18:30–20:24)
Standup Bomb Stories: Burr tells of being called "Billy Bucks" at a disastrous high school prom gig: “That one kid… just looked at me, just went [shakes head]. Like, why did you ever even think?” (41:58–43:16)
Bomb Aftermath: Leifer recalls bombing at a corporate gig—and overhearing the brutal audience review in the restroom.

Quick Comedy Wisdom

First-Time Standup: Both agree—the first 10–15 times up, “It’s just about having the balls to go up there.” (27:00, Burr & Leifer)
Practicing Material: “Do you practice in front of a mirror?” “Yeah. Oh, I’ve tried it. It doesn’t work, right.” (27:48)
Steven Wright’s Advice: “Do standup every night for three years and not judge yourself. To become a really good standup, you have to just go on and go on and fall in your face and bomb. And that’s what it takes to get good.” (28:11, Leifer relaying Wright’s advice)

On Broadway & Acting

Burr’s Broadway Experience (Glengarry Glen Ross): The unique challenge of reading the Broadway crowd, especially for foreigners, and working with Michael McKean. “The only thing that was really—well, because you’re used to, like... me and the crowd. But with other actors, that’s the addition.” (46:11)
Professionalism and Camaraderie: The cast developed ways to keep the show fresh and fun, even joking about mixing up lines for laughs backstage. (47:44)

Notable Quotes

“I needed this book.” (01:03, Bill Burr)
“People are rooting for you. And I think once people know that about giving a speech, it really can calm the nerves.” (09:53, Carol Leifer)
“Five minutes and under. Even if it’s your own daughter.” (06:49, Carol Leifer)
“Just get up there and say who you are to the person … it becomes like an episode of Dateline.” (07:46, Leifer)
“Self-deprecating is always like… it gives them something to root for.” (10:37, Burr)
“There is a war out there for your brain. And they want your brain flatlined, not thinking.” (14:42, Burr, on AI & social media)
“You gotta do standup every night for three years and not judge yourself. ... fall on your face and bomb. And that’s what it takes to get good.” (28:11, Steven Wright advice via Leifer)
“Do your own thing—don’t listen to other people.” (34:09, Leifer)
“The hardest emotion is empathy.” (38:45, Burr)
“If you want to have a good set … and not torture people you love … you want to see 'life of the party' … [this book] is all-purpose.” (56:58, Burr)
“She [Carol Burnett] literally said, 'Send it.' ... Monday she sent the foreword. I mean, who does that?” (57:59, Leifer)

Timestamps for Key Segments

[00:00–01:10] – Burr’s praise for Leifer, introduction of book and theme
[03:18–04:49] – Why people bomb at important speeches, the horror of bad public remarks
[06:33–07:23] – Rule #1: Five minutes or less, and other key writing tips
[08:47–09:45] – Handling nerves, following superstar acts
[09:53–11:15] – The bar is low for civilians, use nerves for energy, self-deprecation
[12:05–13:41] – Worst speech stories, trying AI to write a speech (with hilarious results)
[14:42–15:36] – Distrust of AI, social media, and the dangers of brain-drain
[23:34–24:41] – Leifer’s early standup days, getting passed by Seinfeld & club politics
[27:00–29:09] – Getting started, Steven Wright’s advice, ignoring naysayers
[33:38–34:09] – Dumb old rules of standup, evolution of comedy
[41:03–43:16] – Standup horror stories: prom gigs, brutal audience feedback
[46:11–48:55] – Burr’s Broadway experience, reading the crowd, working with Michael McKean
[54:05–55:36] – Paying tribute to previous generations, club/circuit history
[57:59–58:24] – Carol Burnett’s generosity, writing the foreword for Leifer
[58:56–59:07] – Where to purchase the book, closing thanks

Tone & Language

Conclusion

Recommended for:

Anyone writing a speech
Standup comedy fans/historians
Fans of candid showbiz stories and sharp, funny conversation

“How to Write a Funny Speech” by Carol Leifer is available everywhere books are sold.

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Comedian Carol Leifer 'How To Write A Funny Speech' | Thursday Afternoon Monday Morning Podcast 8-21-25

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Summary

Monday Morning Podcast

Episode Overview

Key Discussion Points & Insights

Why Write a Funny Speech Book?

Essential Speechwriting Tips

The Pain of Watching Bad Speeches

On Stage—Standup vs. Ceremonial

Comedy Career Reflections

The Evolving Comedy Landscape

Memorable Showbiz Anecdotes

Quick Comedy Wisdom

On Broadway & Acting

Notable Quotes

Timestamps for Key Segments

Tone & Language

Conclusion

Summary

Monday Morning Podcast

Episode Overview

Key Discussion Points & Insights

Why Write a Funny Speech Book?

Essential Speechwriting Tips

The Pain of Watching Bad Speeches

On Stage—Standup vs. Ceremonial

Comedy Career Reflections

The Evolving Comedy Landscape

Memorable Showbiz Anecdotes

Quick Comedy Wisdom

On Broadway & Acting

Notable Quotes

Timestamps for Key Segments

Tone & Language

Conclusion