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Book Reviews:
The Gutfeld Monologues (2018), and The King of Late Night (2023) by Greg Gutfeld Read in July 2025 Reviewed in August 2025 by Kris Freeberg, Economist |
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August 10, 2025
Like Ronald Reagan, Donald Trump, Tulsi Gabbard, Amala Ekpunobi, Xaviaer DuRousseau, and many others, Greg Gutfeld is a former Liberal / Democrat.
King of Late Night was published in 2023, and it shows Jimmy Fallon clinging to Greg's left leg in a meme inspired by Chevy Chase's 1983 comedy film "Vacation." Three days ago (8/7/25), Greg appeared on Jimmy's show, where they embraced, and recounted an earlier time when they also embraced.
So these two fellows have been clinging to each other "like a Golden Retriever" and good-naturedly hob-nobbing for a long time. They're buddies.
(And about politics, Greg says of Jimmy, "He didn't join the Left. He was drafted.")
And last month - July 17, 2025 - Stephen Colbert announced that his show is being cancelled.
Gutfeld has had a lot of jobs, and been fired from most of them. His background isn't in comedy; it's in magazine editing.
Be that as it may, he has been doing a late night comedy show. Here's how he has compared with the others lately:
Like Ronald Reagan, Donald Trump, Tulsi Gabbard, Amala Ekpunobi, Xaviaer DuRousseau, and many others, Greg Gutfeld is a former Liberal / Democrat.
King of Late Night was published in 2023, and it shows Jimmy Fallon clinging to Greg's left leg in a meme inspired by Chevy Chase's 1983 comedy film "Vacation." Three days ago (8/7/25), Greg appeared on Jimmy's show, where they embraced, and recounted an earlier time when they also embraced.
So these two fellows have been clinging to each other "like a Golden Retriever" and good-naturedly hob-nobbing for a long time. They're buddies.
(And about politics, Greg says of Jimmy, "He didn't join the Left. He was drafted.")
And last month - July 17, 2025 - Stephen Colbert announced that his show is being cancelled.
Gutfeld has had a lot of jobs, and been fired from most of them. His background isn't in comedy; it's in magazine editing.
Be that as it may, he has been doing a late night comedy show. Here's how he has compared with the others lately:
(Graphic courtesy of ChatGPT)
As his popularity grew, he would show up on my Youtube feed. At first I ignored him because I don't like sneering, snarky, lowbrow jokes at other people's expense, which I could tell he was obviously doing regularly.
Eventually, however, I became curious about his growing popularity. What was resonating?
So I sort of held my nose and slogged through the segment of insulting jokes, and made it to what he calls his Monologues. Listening to a few of them, I was impressed that, here is an independent and brave thinker who isn't afraid to tell it like it is; or at least, as he sees it. I admired that about him.
Then I thought, I sure would like to have transcripts of his monologues that I could just study without wasting my time slogging through the snarky, sneering, sophomoric insults.
So I Googled "Gutfeld Monologues" and guess what? He published a book by that very title.
But it was a little stale. 2018.
So I scrolled around to see what else he had published, and chose the other one, published in 2023. I thought these two ought to give me a good cross section of the guy's thinking and development, help me understand him and his appeal.
Observation: People like Greg Gutfeld fascinate me. The world is full of them. They seem to be ADHD, scatterbrained. They seem impulsive and unpredictable. They're transparent with their emotions, and governed by them. They're forces of nature, hard to pin down, constantly in motion.
People like that need people like me to help them regulate, maintain perspective, review the past and plan for the future, and otherwise develop their "Executive Functioning Skills" because left to their own devices, they're constantly in the moment, trapped in the narrow confines of the ever-fleeting present. I find that my most appreciative, loyal, long-term clients share these traits.
What's different about Gutfeld, and people like him, is that he DOES wear his emotions on his sleeve, so he is free to laugh, and he does. When he laughs, it's authentic and from the belly. People like that. It's also obvious when he's angry about something that is false or unjust. Either way, he's authentic.
One of the "flips" that he points out in the second book is how in the past, Conservatives / Republicans were the humorless "scolds" and Liberals / Democrats were the lovers of fun. Lately, he says, that has flipped. Now the former are laughing and having fun, and the latter are the scolds.
To be aware of either, or of any of that, one must be authentically emotional, which Gutfeld is. I think that's a big reason why he resonates.
I think the bottom line with Greg, and people like him, is that they are intensely caring. They care so intensely about such an overwhelming number of things that, well, they come across as both overwhelmed, and overwhelming. While some of us can compartmentalize or just not give a damn, people like Greg can't. They can't not care.
So they think, think, think, and talk, talk, talk, until something gives: either they find their niche and become famous and popular, or they don't, and fade into oblivion leaving a wake of burned bridges (like all of his firings).
So if you're one of those, it's all about finding your niche, which Gutfeld, now in his 50s, has done.
People like that need people like me to help them regulate, maintain perspective, review the past and plan for the future, and otherwise develop their "Executive Functioning Skills" because left to their own devices, they're constantly in the moment, trapped in the narrow confines of the ever-fleeting present. I find that my most appreciative, loyal, long-term clients share these traits.
What's different about Gutfeld, and people like him, is that he DOES wear his emotions on his sleeve, so he is free to laugh, and he does. When he laughs, it's authentic and from the belly. People like that. It's also obvious when he's angry about something that is false or unjust. Either way, he's authentic.
One of the "flips" that he points out in the second book is how in the past, Conservatives / Republicans were the humorless "scolds" and Liberals / Democrats were the lovers of fun. Lately, he says, that has flipped. Now the former are laughing and having fun, and the latter are the scolds.
To be aware of either, or of any of that, one must be authentically emotional, which Gutfeld is. I think that's a big reason why he resonates.
I think the bottom line with Greg, and people like him, is that they are intensely caring. They care so intensely about such an overwhelming number of things that, well, they come across as both overwhelmed, and overwhelming. While some of us can compartmentalize or just not give a damn, people like Greg can't. They can't not care.
So they think, think, think, and talk, talk, talk, until something gives: either they find their niche and become famous and popular, or they don't, and fade into oblivion leaving a wake of burned bridges (like all of his firings).
So if you're one of those, it's all about finding your niche, which Gutfeld, now in his 50s, has done.
The two books are structured differently. The first is a thematic collection of his monologues from the show "The Five" which has also grown a lot in popularity over the past several years. They're grouped by theme, and then by date between 2012 and 2018.
The themes are:
(Upon review, I notice how each chapter ends with "Where Are We Now?" sections on pages 43, 82, 138, 200, 229, 270, and 293, which I have tabbed for future reference.)
The second book is entirely different. There is one theme that runs through it, from end to end: "The Flip." ("How I got away with flipping the entertainment world upside down.") He shows how he, and others, "flipped the script", thereby popularizing themselves and their ideas, winning the contest to gain society's attention and agreement.
The themes are:
- Identity Politics
- Law & Order
- Hollywood
- Islamic Terror
- The Environment
- The Campus
- The Sexes
(Upon review, I notice how each chapter ends with "Where Are We Now?" sections on pages 43, 82, 138, 200, 229, 270, and 293, which I have tabbed for future reference.)
The second book is entirely different. There is one theme that runs through it, from end to end: "The Flip." ("How I got away with flipping the entertainment world upside down.") He shows how he, and others, "flipped the script", thereby popularizing themselves and their ideas, winning the contest to gain society's attention and agreement.
- From Incompetence to Charm
- From Fear to Curiosity
- From Hawk to Dove, and vice-versa
- From Apathy to Energy
- From Noisy to Silent (his critics)
- From Pacifist to Hostile
- From Science to Peer Pressure
- From Formality to Familiarity (and teasing)
- From fearing firing, to wanting it
- The Twitter Flip: from censorship to freedom of expression
- The Gender Flip: from biology to opinion. Men in girls' bathrooms & sports. Mutilating children. "The flip means the deliberate death of a gay person, turning him into a her." I never thought of it that way.
- The Age Flip in comedy: younger comedians became serious, cautious, and conformist, while older comedians became jovial, daring, and individualistic. "The older you get, the less time you have to care about what other people think" (128).
- The Five flipped the script by becoming The Cool People Who Have Fun, which is what Liberals used to be (133).
- He flipped Cancel Culture with what he calls "Vice Signaling" (150) in which he (essentially) confessed his sins in open, as he went, so there was no secret dirt for anyone to find. (Honesty is the best policy.)
- From Cranky Hermit to Outgoing Fool (181)
- "It's a weird flip, to see that the edgy performer now is no different than the frightened high schooler dependent on fitting in, rather than standing out" (190).
- "Hoax Exhaustion": "The media and the public have flipped. It's no longer the media telling us what's news, but the reverse. The public no longer buys what the media is selling, understanding that most news is manufactured and curated for clicks and profits. Now that they know that, they dictate the terms. It's the best flip ever" (191).
- PJ O'Rourke flipped politics by making right wing politics appealing to people on the left, showing how they could be conservative and still be edgy, fun, and complex (193-204).
- "The people who claim to be anti-McCarthyism are now becoming experts at it" (re: blackballing of conservative comedy writers in Hollywood, page 214).
- Bill Maher's flip: he used to be partisan. Now he's fair (216).
Noteworthy Monologue Quips & Quotes
Noteworthy King of Late Night Quotes
- When Law & Order deteriorate, minorities suffer the most (47).
- He coined the term "Islamophobia-phobia" which is the fear of being accused of Islamophobia (187).
- ". . . the more removed you are from real threats, the dumber you are about (them)" (201).
- "Once you focus on actual stats, the story dies" (211).
- "When we make the group more important than the individual, it never ends well" (244).
- "I believe colleges are dying. Now thanks to the Internet, real knowledge is free and easily curated" (270).
- "Smith & Wesson does more for empowering women than feminism ever could . . . the fact is, keeping a piece is the only way to keep the peace" (273-4).
- "Campus outrage is big over the little things and tiny over the big things" (286).
- "We are now becoming an "allegation nation" (284).
Noteworthy King of Late Night Quotes
- "The show was, in a way, designed to be a little cocktail party with my favorite people, and the viewers were invited" (172).
- "We were witness protection for the fleeing left. And they loved it" (173).
- " . . . always get a head start on tomorrow's work . . . Past Greg should always do a favor for Future Greg" (179).
- Whenever you're outnumbered by detractors, ask them, "Do you ever wonder why I would choose the harder path? Aren't you curious as to why I would make myself less popular, rather than more?" (184)
- Reading PJ O'Rourke's Republican Party Reptile was the beginning of his red pill journey (200).
- "I maintain that I'm not a comedian at all, I'm an editor. Maybe it's time for me to flip from non-comic to comic" (217-218).
- "Conformity Fascists" are lemmings who are violently angry that you aren't leaping off a cliff with them (223).
What do I conclude from all of this? Well, I feel like I understand Gutfeld's appeal better now. I'll never like his sneering, snide, snarky, sophomoric sarcasm, but America does, and that's good for me to know.
Sometimes he's angry for good reason, and I'll give him that. I don't expect him or anyone to be a saint, although I'm pleasantly surprised when they are.
There will always be demand in the world for edgy personalities like Archie Bunker, George Carlin, Howard Stern, Rush Limbaugh, Rosie O'Donnell, Roseanne Barr, James Carville, Jasmine Crockett, and of course Donald Trump.
Personally, I don't care for, or about, anyone's edginess. Often, I think they're being edgy to compensate for a lack of substance, more sizzle than steak if you get my meaning. Or as they say in Texas, all hat and no cattle.
But in Greg Gutfeld's case, he has his reasons for being edgy that I respect. From a very early age he has been a reader, writer, and thinker; and now, in his 50s, he is capitalizing on that wealth of knowledge, experience, and talent.
More power to him, to our country, to our society, and to our culture, about which he obviously cares so much.
Sometimes he's angry for good reason, and I'll give him that. I don't expect him or anyone to be a saint, although I'm pleasantly surprised when they are.
There will always be demand in the world for edgy personalities like Archie Bunker, George Carlin, Howard Stern, Rush Limbaugh, Rosie O'Donnell, Roseanne Barr, James Carville, Jasmine Crockett, and of course Donald Trump.
Personally, I don't care for, or about, anyone's edginess. Often, I think they're being edgy to compensate for a lack of substance, more sizzle than steak if you get my meaning. Or as they say in Texas, all hat and no cattle.
But in Greg Gutfeld's case, he has his reasons for being edgy that I respect. From a very early age he has been a reader, writer, and thinker; and now, in his 50s, he is capitalizing on that wealth of knowledge, experience, and talent.
More power to him, to our country, to our society, and to our culture, about which he obviously cares so much.
