The Daily Beast
Photo Illustration by The Daily Beast / Photo via GettyFor Greg Gutfeld, the transition from irreverent satirist to true believer has been lucrative, to be sure, but also—like much of the vast reshaping of the conservative media landscape over the past four years—defined by Donald Trump.During the eight years Gutfeld presided over Red Eye—the freewheeling, absurdist, often uproarious show that attracted fans like legendary Saturday Night Live writer Jim Downey and aired between the witching hour and dawn—Gutfeld, along with his former friends Bill Schulz and Andy Levy (who both declined to comment for this story), pioneered a transgressive sort of television that could only have occurred while most aging Fox News viewers along with Roger Ailes and other top executives were fast asleep.“It wasn’t like anything else on TV,” Downey told The Daily Beast, adding that he began watching Red Eye in its early days, around 2007 or 2008, during 3 a.m. bouts of insomnia. “I was impressed by the originality of the whole operation, and I thought it was a nice mix with those three [Gutfeld, Schulz and Levy]. It was sophomoric, and I mean that as a compliment.” Schulz, who made no secret on the air of his fondness for adult beverages, was fired from the show in 2013.These days the 56-year-old Gutfeld, whose eponymous 11 p.m. weeknight program Gutfeld! debuted on Fox News last week to largely hostile reviews but robust ratings, has, by some appraisals, morphed from zany rebel to company man, and from rule-breaking joker to handsomely compensated ideologue (at a rumored $4 million a year).The second Fox News offering with his name in the title—the first aired on Saturday nights for six years starting in 2015—Gutfeld’s latest show thus far has largely consisted of crude parodies of rival personalities on other networks, sneering attacks on Joe and Hunter Biden, repeated warnings about the lying mainstream media, and an amen corner of familiar Fox News panelists, including new hire and former Trump mouthpiece Kayleigh McEnany, attempting variations on owning the libs.All of which has been enough for Gutfeld! to hammer not only MSNBC’s Brian Williams and CNN’s Don Lemon in the Nielsens (an average of 1.57 million total viewers to Williams’ 1.323 million and Lemon’s 668,000), but also every late-night comic with the exception of CBS’ Stephen Colbert.He has also managed to hold much of The Ingraham Angle’s audience (although namesake Laura Ingraham was off last week), and improve significantly on the ratings of his predecessor in the time slot, news anchor Shannon Bream.Gutfeld, not surprisingly, has a reputation among some Fox News employees as demanding, remote, and difficult to work with, although possessed of nowhere near the megalomania that characterizes what a current staffer called “anchorzillas.”“He just doesn’t come off as approachable,” said a current Fox News staffer. “So many anchors like Dana Perino and Harris Faulkner are lovely in the elevator and in the lobby, even if they don’t know you. Greg doesn’t even make eye contact. Judge Jeanine, who people would peg as intimidating, is way more friendly and takes time to talk to you. Greg, I feel like, is the person who you could meet 15 times and he still wouldn’t remember your name.”“The more he started succeeding, the less he started talking, the less he started socializing,” said a former Red Eye guest who frequently attended the raucous post-show wrap parties at a nearby bar. “I never thought it was originally intentional and then it seemed or appeared that it was. Ultimately, it was intentional.”This person added: “No ifs ands or buts, Gutfeld had no appreciation for Bill and Andy, nor did the network. It was the three of them that made Red Eye a success…When you’re talking about friends and colleagues, loyalty is a human thing, it’s not a Fox News thing.”On his premiere, Gutfeld was hardly burdened by humility.“As for those late-night shows we’re supposed to compete against, why bother?” he crowed to his viewers during his opening monologue. “Who do they offend? The only time Stephen Colbert ruffles feathers is in a pillow fight. The definition of risk to Kimmel is dehydration from crying too much. Fallon, that guy fawns more than a herd of deer. And I heard Seth Meyers and Trevor Noah ran off to be obscure together.”“Red Eye was funny,” former Fox News anchor Juliet Huddy, an erstwhile regular in Red Eye’s “leg chair,” told The Daily Beast. “This is not funny.”A second “leg chair” veteran from Gutfeld’s Red Eye days, who asked not to be further identified, described his metamorphosis with a pop-music analogy: “He’s gone from being Eric Clapton to Pat Boone.”Another frequent Red Eye guest, Reason magazine editor-at-large and libertarian Nick Gillespie, told The Daily Beast: “I do think he’s more conservative than he used to be”—for instance, continuing to favor the legalization of controlled substances but becoming increasingly disapproving of the folks who abuse them, Gillespie said. “He still delights in making fun of sanctimonious media and culture and political figures.”A fourth Red Eye alum told The Daily Beast: “He’s gotten meaner. Greg always had a kind of a dark side when he was coming up and hungry, but now he’s meaner and smugger. I can’t tell if it comes out in his television commentary, but it certainly comes out in his personal interactions.”Former Fox News digital journalist Diana Falzone, a co-author of this story, also appeared on Red Eye from time to time and left the network in 2018. Gutfeld and Fox News declined to comment.An ex-Fox News employee described Gutfeld’s rise this way: “I think he’s talented and an insanely good writer, although his delivery is a little too angry for my taste. But I think he’s a hypocrite because he tried to always play himself off as anti-establishment—‘I’m not one of them’—and then ratings came and his name on a show came, and now he’s staying within the script. He’ll be successful because anything you put up at 11 o’clock on Fox is gonna work.”This person added: “He was pretty nasty and mean when it came to Trump early on, but when he realized pro-Trump worked, he flipped to pro-Trump and he got his audience… Leading up to the 2016 election, he was wrecking Trump nightly on The Five. A little while into it he realized that that’s not what the audience wanted to hear. So he softened his tone and assumed a pseudo pro-Trump stance.”Former Democratic Party operative Bob Beckel, a designated liberal on The Five until he went on leave to address substance abuse problems in 2016 and then was fired in 2017 (allegedly for making a racially insensitive quip to a Black computer technician), told The Daily Beast: “The Trump thing was a real switch for Greg. He has always been very ambitious, but he’s earned his jobs. What changed him in terms of his politics on Trump? I’ve got to think that to be against Trump in that building was not a very safe place to be. Self-preservation kicks in at some point.”Indeed, there was a time when Fox News’ resident comedian was one of Trump’s harshest critics instead of what he later became during the reality-show billionaire’s divisive presidency—an often-obsequious cheerleader who once claimed that Trump had purposely exposed himself to COVID-19 as an act of courage, heroism, and patriotism.Six weeks after the election that the 45th president lost decisively to Joe Biden, Gutfeld rationalized the violent and lethal Jan. 6 insurrection at the Capitol by explaining that “what we’re seeing here is a lot of people with no hope” and “you have millions of people who do not trust their institutions, and you know what? They are justified. You can’t trust the media, because they lie to you. You can’t trust the elections, because there is fraud!” (Former colleagues of Gutfeld’s are often quick to note that he was a huge early booster of Gavin McInnes, a Vice co-founder and Red Eye regular who went on to create the Proud Boys, a far-right extremist group that played a key role in January’s violence.)Fox News Host Greg Gutfeld: Trump ‘Put Himself on the Line’ and Got COVID ‘For Us’That was a far cry from Gutfeld’s drumbeat of disapproval during the 2016 campaign, when he accused Trump’s media acolytes, especially Fox News colleagues like Eric Bolling, of “Trumpsplaining” away the Republican frontrunner’s “making fun of a disability, making fun of John McCain, making fun of women, a woman’s face…Because it never ends. No one will ever stop defending the crass stuff he says…I’m sick of hearing people defend this stuff."In his Dec. 23, 2015 appearance on The Five, Gutfeld even bit the hand that feeds him: “But somehow we’re gonna have him [Trump] on our network all the time…When you are surrounded by toadies that cheer you on, you’re like a comedian and you like the laughter…Instead of thinking about what he says, he’s impulsive and it makes you wonder, do you want an impulsive leader or do want a leader that thinks?”Keenly aware of how his whiplash-inducing conversion would inevitably be perceived, Gutfeld tried to frame his previous fear and loathing, during an August 2018 onstage interview at the Commonwealth Club of California, as an unwarranted obsession with the words that came out of Trump’s mouth—basically arguing that the statements of a top-tier candidate for president should count for nothing.“I was hypercritical of him, he was driving me crazy,” Gutfeld confided to his interviewer, Dilbert cartoonist Scott Adams. “I was, like, more obsessed with his words, because there were no deeds yet because he wasn’t president. But I had become—arrgh—emotionally invested in his behavior, which was kind of a waste of time… I look back now and I go, I got tied up in his language. Once he became president, I could get tied up on his deeds… When you look at his deeds, there’s not a lot to complain about.”Gutfeld likes to call himself a former liberal who switched brands while in college after his fellow lefties at the University of California at Berkeley annoyed him with what he perceived as their sanctimony and hypocrisy—unattractive traits he had previously ascribed to right-wingers.“Greg was a Berkeley kid,” said a frequent Red Eye guest. “He went to a super-liberal school and his being conservative was a response to that… He’s a Gen X conservative, so he thinks ‘punk rock.’ They misinterpret what punk was, conservative men in their mid to late forties and early fifties. They think it’s shit-talking hippies. Punk rock was a reaction to conservative politics and it’s ridiculous for those men like Greg to compare themselves. Greg has more in common with Margaret Thatcher than with the Sex Pistols.”Occasional Red Eye guest and Gutfeld pal Buzz Osborne, founder and lead guitarist of the grunge and sludge metal band The Melvins, begged to differ.“I don’t think this person understands anything about what punk rock is,” said Osborne, adding that he never watches cable or broadcast television, much less Fox News. “It’s not against conservative politics. It’s against all politics. Of any kind. It’s a reaction to normalism, whatever that may be. I also think that it celebrates the individual.”Greg Gutfeld Proves, Yet Again, That Conservative Comedy’s Just Stuff Your Drunk Aunt Yells at a WeddingAs for Gutfeld, “I think people underestimate him, and I think it’s a mistake,” Osborne told The Daily Beast. “There’s a lot to be said for guys like him, if people will just have an open mind and listen to him. I think Greg’s extremely funny, and that’s lost on a lot of people.”Gutfeld joined Fox News in 2007 after a checkered career writing for and editing magazines such as Rodale Press’s Prevention and Men’s Health, and two of the late Felix Dennis’ lad mags, Stuff and Maxim U.K.He managed to get fired from all three magazines. The 5-foot-5 Gutfeld—whose repertoire of short jokes is not as prolific as it used to be—lost the Stuff editorship in 2003 after hiring three dwarves to disrupt an American Society of Magazine Editors seminar on “What Gives a Magazine Buzz.” The dwarf-actors were ejected from the seminar for chomping noisily on fistfuls of potato chips and engaging in ear-splitting conversations after letting their cellphones ring and ring.“Greg was let go from virtually every high-profile job he ever had prior to Fox, so when he got to Fox News he did whatever it took to stay in [Fox News Media CEO] Suzanne Scott’s good graces,” said a former insider at the network. “He doesn’t care what colleagues or friends he steps on as long it protects his own position.”Bob Beckel, who had been friendly with his former The Five co-host, said that instinct might have been behind Gutfeld’s decision to flame him on Twitter in October 2019 after Beckel characterized his Fox News firing as a Trump-inspired “setup.”“Shepard Smith is leaving Fox News,” Beckel had tweeted. “I worked at Fox for six years. Shep was a REAL reporter. I attacked Trump daily. My firing was a setup up by people inside & outside Fox. With Shep gone Fox Is no longer a News network. It’s run by Trump. Sadly it will go down with him.”Taking on the role of corporate flack, Gutfeld retorted: “Bob, trump had nothing to do with your firing. In fact Fnc blessed you with many second chances. Using Shep’s classy exit to take this dishonest swipe at a bunch of good hardworking people is disappointing.”“I was really surprised,” Beckel said about Gutfeld’s slam.—With additional reporting by Justin Baragona.Read more at The Daily Beast.Get our top stories in your inbox every day. Sign up now!Daily Beast Membership: Beast Inside goes deeper on the stories that matter to you. Learn more.