Television talk shows generally abide by an unwritten social contract where no matter how dodgy or terrible a guest’s project sounds, the guests and host all pretend it at least has the potential to be good. On a famous episode of Late Night With Conan O’Brien in the late 1990s, however, this unwritten social contract was dramatically, hilariously shattered. In a violation of talk-show etiquette so unexpected that people still talk about it, a guest was brutally honest about what he thought of another guest’s project.

The awkwardness begins early, with guest Norm MacDonald and host Conan O’Brien discussing their respective crushes on guest Courtney Thorne-Smith, then of Melrose Place. Then O’Brien mentions that MacDonald referenced Carrot Top earlier in the show, and in what now appears not to be just a fortuitous coincidence, Thorne-Smith had recently filmed a role as the female lead in Carrot Top’s 1998 starring debut, Chairman Of The Board.

The great thing about MacDonald’s appearance on Late Night—and his talk-show appearances in general—is that it feels like he’s drunkenly, inventively heckling the show from his La-Z-Boy at home, even though he’s a mere foot from Thorne-Smith, and a couple of feet from O’Brien. MacDonald’s delivery of “Wait, she left Melrose Place to do a movie with Carrot Top?” gets a huge laugh, even though it’s less a joke than a setup. A setup like that doesn’t need a punchline, because in any sentence, Carrot Top instantly qualifies as one.

This prompts O’Brien to ask poor Thorne-Smith a question no one should have to answer: “Why a movie with Carrot Top?” The lost expression on her face as she attempts to answer suggests she understands this isn’t a softball question: It’s an existential query that simultaneously demands and defies an easy answer, for society and the film industry, as much as for this luckless actress. Thorne-Smith never directly answers that question, instead mumbling effusively about what a sweet guy Carrot Top is. When O’Brien asks whether she experienced the exquisite pleasure of love scenes with Carrot Top, she nervously jokes it’s just like “9 1/2 Weeks, with Carrot Top.” MacDonald quips, “Is it called 9 1/2 Seconds? Like, he’s a premature ejaculator?” which is a hack joke rendered borderline-brilliant by the context and delivery. O’Brien, who is clearly half concerned and half overjoyed to be losing control of his show to MacDonald, a man he obviously reveres as a comic genius (because he is one), attempts to wrestle control back by asking Thorne-Smith the name of the movie—a pretty harmless question in most circumstances. MacDonald pipes in: “If it’s got Carrot Top in it, you know what a good name for it would be? Box Office Poison.”

The segment’s infamy is attributable partly to the cult of Norm MacDonald, who made his name attacking the phoniness and pretension of pop culture. As a satirist, MacDonald had a sacred professional obligation to go after Carrot Top; it was a rare instance when making a cheap joke at the expense of a walking punchline becomes righteous, even heroic. Pop culture often resembles a reverse meritocracy, one where LMFAO can make tens of millions and Gram Parsons dies at 26. But something just seemed wrong about Carrot Top being given his own movie. The ridiculousness of a seemingly smart, sane woman leaving a hit show to play the romantic interest in a Carrot Top movie had to be confronted.

The clip went viral in a pre-Internet age because there was a sense that MacDonald is speaking for all of us—and for O’Brien as well. He was implicating the movie industry as whole for thinking, “Why not a Carrot Top movie?” But it went even further: MacDonald was also implicating the entertainment industry for making Carrot Top happen in the first place, for rewarding him with the kind of success and visibility that made a multi-million-dollar film vehicle not just possible, but inevitable.

Carrot Top is a walking punchline partially by design. He turned himself into his own biggest, goofiest sight gag. From his name to his signature frizzle of red hair, he made himself an enormously lucrative joke, working the college circuit with such success that Rolling Stone was moved to write an article about how this red-headed freak had come out of nowhere and was making millions, and perhaps most disturbingly and inexplicably, getting laid by a selection of nubile co-eds.

The Rolling Stone profile had such a famously, disturbingly sexual element that a Los Angeles Times writer named Suzanne Fields used it to illustrate the perils of what she describes as the “fast pace, tinsel sensuality and titillating lure of ‘free sex’” that the young people were apparently rebelling against by embracing abstinence, writing:

A long article on a comedian named Carrot Top, who performs in college towns the way Debby does Dallas, illustrates the bleak emptiness of the groupie scene. His performance is largely devoted to getting a good-looking woman to leap between his sheets. He flirts and flatters Beth, a young woman in the audience. She can’t imagine going to bed with this guy unless she’s dead drunk. “Carrot Top flashed his carrot tattoo and told Beth how attractive he found her. All the while, she was gradually moving, drink by drink, beyond her depth, until, with the bar beginning to whirl around her, she was drunk enough to toss off a tell-all comment” that is not printable in this newspaper. At the end of the verbal performance, Beth drives off with Carrot Top. His remark dismissing her the next morning is the moral of this Rolling Stone tale: “That girl is a future restraining order.”

The moral is clear: give in to the fast pace, tinsel sensuality, and titillating lure of “free sex,” and BOOM, the next thing you know, you’re naked in bed with Carrot Top, who has an impatient gleam in his eye that suggests he can’t get away fast enough, and that he thinks he’s the one doing you a favor. That, in this columnist’s mind, is the ultimate danger of the sexual revolution: your daughter fucking Carrot Top.

This hysterical column captures the visceral negative reaction Carrot Top invokes. He isn’t just mocked because he embodies prop comedy, perhaps the lowest and least-respected form of comedy; he’s mocked because on a primal emotional level, he’s disturbing to look at. The shock of red hair, the weirdly smooth, feminine features, the skinny-yet-cut body—it’s all weirdly repellent. In the Late Night segment, O’Brien gets laughs just by repeatedly showing a photograph of Carrot Top, but it’s safe to assume the audience is laughing at the man, not with him. The audience is never laughing with Carrot Top, and he at least has the decency to be an okay sport about always being the butt of the joke.

Carrot Top apologists point out that unlike, say, Gallagher, Carrot Top doesn’t appear to be a hateful human being. On the contrary, he seems like a likable enough guy whose juvenile, idiotic humor isn’t really hurting anyone. The anger directed toward him consequently feels disproportionate, yet not entirely unmerited. Still, re-watching that wonderful Late Night clip, I couldn’t help but discern a passive-aggressive subtext in MacDonald’s comments, since the two starring film vehicles MacDonald got to make, Screwed and Dirty Work, could also be titled Box Office Poison. Hollywood gave MacDonald, a widely revered comedy figure, only one more cinematic chance than it gave Carrot Top.

So why a Carrot Top movie? The answer, not surprisingly, has everything to do with commerce and timing, and nothing to do with art or inspiration. The kids seemed to love Carrot Top (enough to have sex with him!), and if he made millions entertaining drunk, stoned college kids, why couldn’t he make millions entertaining drunk, stoned movie audiences? So Trimark, never the classiest of movie studios, took a calculated risk that he might be able to make it money, the same way Pauly Shore and Jim Varney’s Ernest P. Worrell made big profits for studios while arguably not contributing anything of vital significance to our culture.

Commerce explains the “why” of the Carrot Top movie. It doesn’t explain the “how.” How do you turn a goofy-looking dude whose act consists of making one-liners about odd-looking, homemade contraptions into a movie star? How does Carrot Top function onscreen? Who is he, if not a touring comedian making jokes about props? The answer Chairman Of The Board comes up with is lazy and unsurprising.

Onscreen, Carrot Top is Pee-wee Herman in Pee-wee’s Big Adventure. He’s both a live-action cartoon character and the personification of childhood innocence, a man-child who lives in a massive Rube Goldberg contraption of a house seemingly built from the blueprints of Pee-wee’s home in Pee-wee’s Big Adventure. He’s a kook who lives in his own wacky, whimsical world, and he doesn’t need to grow up: The stuffy squares who comprise the world would be better off adopting his freewheeling approach to existence.

Chairman Of The Board steals shamelessly and ineptly from Pee-wee’s Big Adventure, but it’s just as shameless in its appropriation of Yahoo Serious’ Young Einstein. Serious’ would-be American breakthrough was a wacky slapstick comedy positing young Albert Einstein as a kooky, crazy-haired, surf-happy inventor. Chairman Of The Board is a wacky slapstick comedy about a kooky, crazy-haired, surf-happy inventor named Edison, played by Carrot Top. The problem is that Carrot Top is not Pee-wee Herman. He’s not charming, innocent, appealing, funny, or asexual; he’s creepy, unappealing, and both sexual and sexualized in ways that are deeply disturbing and, like the account of Beth’s lost night in Carrot Top’s bed in Rolling Stone, creepily memorable.

Edison is introduced naked in the shower. Later, when he’s looking for employment, he procures a position in the inspection room at Royal Condoms, where his boss (Jack Riley, credited as “Condom Boss”) finds him on the floor, fucking the boss’ half-naked daughter to prove that the company’s French tickler works.

It’s a throwaway gag that aspires to the taste and sophistication of a “Female Body Inspector” novelty T-shirt, but it invites a slew of disturbing questions:

Did this beautiful woman see having sex with Edison as part of her job, or was she so intensely attracted to him that she decided to have sex with him right there on the floor, despite knowing how angry it would make her father? In the world of Chairman Of The Board, do all women find Edison inexplicably irresistible, or just this particular employee of Royal Condom? Why is Chairman Of The Board forcing us to think about Carrot Top’s penis, and what he does with it? What kind of monster does that?

Later, after smashing his arch-rival in the nuts with a tennis ball, Edison seeks the services of a buxom tennis instructor played by Cindy Margolis (once Guinness’ world-record holder for Internet download popularity), who suggestively massages a pair of tennis balls and strokes her racquet, moaning, “Well, Edison, to master the game, you need to get zen about it! You have to feel the balls, caress them, instead of whacking them. And think of your racket as an extension of yourself, another muscle—strong, hard, forceful, a tool to penetrate your opponent’s court!” While she lewdly caresses her double entendres, Carrot Top moans and contorts his face to suggest he’s experiencing a powerful orgasm.

Edison’s romance with Natalie Stockwell, Thorne-Smith’s character, is comparatively tame and wholesome by comparison. Their big scene together involves Natalie belching the alphabet while on a lunch date at a museum. Yet it’s worth noting that every moment Thorne-Smith is onscreen, she looks visibly more awkward than she did during the Conan segment, a television spot that has become famed for its awkwardness. All Thorne-Smith is called upon to do here is force smiles and act like she’s attracted to, and impressed by, a character played by Carrot Top. And yet she is utterly defeated by those demands.

Chairman Of The Board begins by shamelessly ripping off Pee-wee’s Big Adventure, then purloins its central plot point from Melvin And Howard when Edison stumbles upon Armand McMillan (two-time Academy Award nominee Jack Warden, who also co-starred opposite Norm MacDonald that same year in Dirty Work), the free-spirited, surfing genius behind McMillan Industries, a company so committed to ideas and innovation that high atop its headquarters sits a giant lightbulb with the words, “Where Idea Is King.” By all accounts, Armand was a magical man-sprite whose life was all about loving people, riding killer waves, and inventing things, yet the research-and-development department of his company—you know, the one with the giant lightbulb at the top to convey its zeal for researching and developing things—left him a husk of a man presiding over a sad roster of shuttled projects. This living embodiment of impish joy and exuberant kindness lets Bradford (Larry Miller), his sadistic, misanthropic, black-hearted villain of a nephew, rule over the company with an iron fist. That is, until Armand meets Edison, and is so blown away by what I suppose would have to be his charm and likability (it’s difficult to say, because Carrot Top gives a performance devoid of charm and likability) that when he dies, he leaves Bradford his surfboard, and Edison his company.

At this point, the film becomes a Spuds Mackenzie variation on The Hudsucker Proxy, as the wacky young boss gets a bunch of uptight, old business-type dudes (whose ranks include the great M. Emmet Walsh) to loosen up and embrace their inner Van Wilder, while his nemesis tries to drive down the stock price to the point where he can take over. First, Edison wins their favor by getting them to play Twister. Then he inspires a new golden age of productivity for the company by instituting a weekly luau, complete with a designated area where the sad old men can mosh in safety and comfort. How crazy is this luau? At one point, a dog shows up—on a surfboard!

Edison’s innovations, like a lie-detector shirt that emits loud fart noises when the wearer is lying (the film never quite explains why someone would voluntarily agree to wear a shirt that promises to humiliate them while exposing their deceptions) and a TV dinner with an actual TV attached (available in such timeless flavors as Beavis & Broccoli, N.Y.P.D. Blueberry Pie, and Chicken, Corn, and M*A*S*Hed Potatoes) make him the most successful entrepreneur in the world. Yet in a puzzling development, Edison still struggles to come up with the money to pay rent on the beach-side shack he shares with his two best buddies.

Carrot Top’s character is designed as a lovable dreamer, but he comes off as creepy, repellent, sexist, and deeply mentally ill, an oblivious jerk whose life is filled with cruelty and sadism, whether he’s ripping the necktie off a corpse to look better at Armand’s funeral, or trying to intimidate little girls during an audition for the lead in Annie. Whatever tacky magic Carrot Top has or had as a live performer, he lacks as a film actor. The question isn’t whether this Carrot Top movie will be good or bad, but whether it will be merely bad, or the fucking worst. (It’s the second thing.)

Chairman Of The Board epitomizes the mindless optimism and go-go confidence that characterized the 1990s dot-com bubble, when the idea really was king, brash young men with crazy ideas were heralded as the saviors of both the economy and society, and irrational exuberance was the order of the day. Technology was going to change the way we lived and worked, and usher in a utopia. Dreamers with silly ideas were suddenly afforded a level of respect and importance that now seems delusional. It was an age where we threw money at the longest of long shots, be it a gamble that a medical-information website fronted by former Surgeon General C. Everett Koop would become a billion-dollar commercial dynamo, or that a red-haired prop comic whom much of the public nursed a strong desire to punch in the face might become a major movie star, like Cary Grant or Pauly Shore.

The public coldly rejected both Chairman Of The Board and Carrot Top as a movie star. The film is currently ranked as the 51st worst film of all time on IMDB, and Mystery Science Theater 3000’s Mike Nelson, who knows something about bad films, listed it as one of the five worst comedies of all time for Cracked.

Carrot Top never starred in another film, but director Alex Zamm has gone on to continue the saga of some of our shittiest franchises in his direct-to-video work on projects like Inspector Gadget 2, Dr. Dolittle: Million Dollar Mutts, Beverly Hills Chihuahua 2, Tooth Fairy 2, The Little Rascals Save The Day, and, coming in 2015 to a Netflix queue near you, Jingle All The Way 2.

That last film reunites Zamm with Tooth Fairy 2 star Larry The Cable Guy. I like to imagine that when Larry The Cable Guy and Carrot Top see each other at a Las Vegas casino or pricey Beverly Hills restaurant (as they must), they nod and exchange a deep, soulful look that wordlessly but powerfully conveys the unspoken but profound connection between them. Beyond their collaborations with Zamm, these men understand what it’s like to have your existential humiliation and enduring success inextricably intertwined, to be worshipped and reviled for the same stupid shtick. They understand what it’s like to stop being a human being with dignity (Scott Thompson in the case of Carrot Top, Dan Whitney in Larry The Cable Guy’s case) and become a cartoon character and walking punchline in exchange for fame, money, and power. In a perfect world, someone like Quentin Tarantino would salvage these broken, degraded icons and pit them against each other in a film that would reinvent both their careers by stripping away all the bullshit, and getting to the sadness and desperation at their core.

Chairman Of The Board really is as terrible as its reputation suggests, but there’s something oddly poignant about it all the same. It exemplifies a curious time when anything seemed possible, even the notion that Carrot Top might be a major movie star. Some dreams, however, prove too preposterous.

Next: David Byrne’s True Stories