The greatest one-off Simpsons character ever began with James Bond. When Greg Daniels worked as a producer on the show, he always wondered what it would be like to write an episode from the perspective of one of the dim-witted henchmen who populate the iconic British spy’s movies. You know, the kind of easily thwarted lackey the supervillain unleashes on 007 while plotting to take over the world.

The goon doesn’t even understand the point of the bad guy’s plan. "It’s just a job for him," said Daniels, who naturally imagined Homer in that role. The comedy, according to Daniels, "is that Homer is not aware that his new job is as a henchman for a Bond villain. It’s just the audience that’s aware of it."

For that bit of dramatic irony to generate laughs, Homer needed a new boss. But not just any boss. He had to be a charismatic guru and a ruthless megalomaniac. Blend those two personae together and you get Hank Scorpio. He’s the bearded president of the Globex Corporation, a nefarious shell company that hires Homer away from the Springfield Nuclear Power Plant then relocates the Simpsons to a lush planned community, Cypress Creek. Scorpio looks like a young Richard Branson but could be a funhouse mirror image of any eccentric billionaire. He dresses like a crunchy square, adores hammocks, hates the word "boss," and enjoys flashing his psychopathic streak (more on that later).

Since appearing in "You Only Move Twice," which aired on Fox 20 years ago next month, Hank Scorpio has become an archetype. These days, New Age rich dudes aren’t just nauseatingly idealistic. Their ambition leads them to routinely engage in cartoonish, Scorpio-like behavior. They stage $10 million Lord of the Rings–themed weddings on "ecologically sensitive" land, propose splitting California into six states, and fund organizations that explore the feasibility of building independent floating cities in the middle of the ocean.

"That’s one of the funny things about this episode," said Josh Weinstein, who with his writing partner Bill Oakley co-ran the animated behemoth’s seventh (1995–96) and eighth (1996–97) seasons. "It’s really prescient." Almost two full decades before Silicon Valley was doing it regularly, The Simpsons was gleefully punching holes in the excesses of tech culture.

"That might’ve been one of the best stories I pitched," said Daniels, who went on to adapt The Office for American television and cocreate Parks and Recreation. But soon after offering up the Homer-as-Bond-henchman concept at a story conference, he left to join Mike Judge in launching King of the Hill. To make the idea sing, The Simpsons then turned to a pair of late 20th-century comedy titans.

The first was John Swartzwelder, to whom Weinstein and Oakley assigned the episode. Over the last quarter century, the press-shunning David Crosby look-alike has been mythologized more than any other comedy writer. Swartzwelder’s Wikipedia entry is a collection of possibly apocryphal but occasionally well-sourced details, including several claims that he may not actually exist. In an interview with Mike Sacks for his book Poking a Dead Frog: Conversations With Today’s Top Comedy Writers, former Late Night With David Letterman and Saturday Night Live writer Jim Downey tells a story about Swartzwelder — who he estimated stood "about six foot eight" — self-sabotaging an early-’80s job interview with Letterman.

"Swartzwelder is holding forth, as I recall, about his views on television, which amounted to everything on television was shit," Downey told Sacks, "including, I think, much of what we had done on our show. Dave looks over at me and his eyes tell me, ‘No way.’" Swartzwelder didn’t get hired, but landed at SNL before eventually moving on to The Simpsons.

His colleagues have stories. They’re all real. Allegedly. According to Daniels, Swartzwelder followed the advice of a doctor who recommended only short bursts of exercise. "He would walk down the street in his street clothes," Daniels said, "and then he’d just run flat-out like a demon for 30 seconds." Weinstein remembered once planning a party and inviting Swartzwelder. "He just sort of laughed," Weinstein said, "and he’s like, ‘I don’t do that sort of thing.’"

An internet rumor once spread that Swartzwelder was the inspiration for Parks and Recreation’s Ron Swanson. There was a resemblance, but it wasn’t true. In July he joined Twitter, where he posts only lines from his set of detective novels. (By my count, Swartzwelder is the only person with an egg avatar worth following.)

Swartzwelder’s legend is indeed considerable, but it shouldn’t outstrip his brilliance. "You can safely say maybe like 5 percent of The Simpsons’ greatness is specifically Swartzwelder," Weinstein said, "if not more." That estimate is a little low. Swartzwelder has written 59 Simpsons episodes, which is the most of any writer in the show’s 20-year history and almost 10 percent of the series’ nearly 600 half-hour installments.

If you ask other writers about Swartzwelder, they’ll tell you that he’s sui generis. "I’m a peer of his in the sense that I worked on the same TV show," Daniels said. "But his background and his point of view is so unique that it’s hard to really think of him as having a lot of similarities to other writers."

Swartzwelder’s frame of reference often fell outside of the television age. His comedy was informed by all sorts of old-timey entertainment — W.C. Fields, Laurel and Hardy, Preston Sturges, radio crime dramas. In a New Yorker article published in 2000, fellow Simpsons writer George Meyer described one great Swartzwelder joke as "a horrifying idea juxtaposed with something really banal — and yet there’s a kind of logic to it."

A Swartzwelderian juxtaposition can be found early in "You Only Move Twice." After Homer is offered the job from Globex, he shows his family a short film promoting the company town of Cypress Creek. The movie begins with shots of dilapidated buildings and a man saying, "Somebody oughta build a town that works!" The narrator then responds with, "Somebody did!" At that moment, parking meters magically become trees, four different storefronts transform into coffee shops, a dumpster morphs into a coffee cart, and finally — and most disturbingly — a homeless man turns into a mailbox.

The hideously extreme gentrification fantasy feels less far-fetched in 2016 than it did in 1996. In late August, Bloomberg reported that the median home value in Palo Alto had surged to $2.5 million. Three weeks prior to that, a city housing commissioner resigned and moved out because she could no longer afford to raise her family there.

Although it presumably had slightly more reasonable housing prices, Cypress Creek was devised by The Simpsons writers as a stand-in for a place like Palo Alto. They originally dubbed it "Emerald Caverns" before changing the name to what they figured sounded more like a town in Silicon Valley. At the time, however, the most famous tech company in the world was Redmond, Washington–based Microsoft. For that reason, the show’s animators gave the new set the feel of the Pacific Northwest, filling it with mountains and trees. (The Globex headquarters does sort of resemble Google’s glass-encrusted complex, even though the latter corporation wasn’t founded until 1998.)

Mike B. Anderson, who directed "You Only Move Twice," likened working on the episode to putting together a Simpsons Halloween special. Visually, he said, "every single thing is new." Including Cypress Creek’s most powerful iconoclast. Daniels originally envisioned Homer’s new boss as an Ernst Stavro Blofeld–like figure. In You Only Live Twice, he’s the scarred, cat-stroking, nuclear-war-escalating Bond nemesis who also inspired Dr. Evil. Instead, Hank Scorpio was given a slick, earthy vibe. Anderson recalled Oakley seeing the character’s final look and saying, "It’s perfect."

But Scorpio still needed a voice. Hank Azaria, who plays Moe, Chief Wiggum, and Comic Book Guy (among many other characters), initially recorded the part as a placeholder, but Oakley and Weinstein had someone else in mind.

By the mid-’90s, Albert Brooks was a Simpsons institution. Shortly after Brooks earned an Academy Award nomination for his role in James L. Brooks’s Broadcast News, the Simpsons producer enlisted him for his new animated series. Albert Brooks appeared in two first-season episodes, first as RV salesman Cowboy Bob and then as Marge’s French bowling instructor, Jacques. He popped up again in the fifth season as self-help guru Brad Goodman. Oakley and Weinstein thought that he’d be perfect for Hank Scorpio.

"Albert Brooks is a brilliant, insane ad-libber," Weinstein said. "We knew that we didn’t have to get the jokes perfect." During the marathon recording session, Brooks was hard on himself in a way that may sound familiar to those who know his work. "No, that’s not good," Weinstein recalled him saying. "That’s not funny. Let me try something else." Weinstein, who has a fantasy of finding the two-hour tape of Brooks as Scorpio and making an extended version of "You Only Move Twice" with it, said that 80 percent of the lines the actor came up with were funny.

"By the end of that session, I don’t think I had another comedy thought in my head for a month," Brooks said in 2012. "I said every funny thing I had as Hank Scorpio."

Brooks delivered an all-time great performance, but what made it even better was that while he repeatedly went off script, Dan Castellaneta, the voice of Homer, riffed off of him in character. So in the episode, Homer’s reactions to Scorpio are real.

Thus it makes sense that when Hank frantically drops by the Simpsons’ new house in Cypress Creek to introduce himself and drop off a fruit basket, Homer seems overwhelmed. Scorpio is also visibly antsy by design. "You want him to perform like he’s thinking of two things at once all the time," Anderson said of the character, who we soon learn isn’t just the president of Globex Corporation. Scorpio gets miffed when Homer refers to him as "boss," quickly jumping into a mellow tirade that contains the kind of performative benevolence displayed now by certain self-righteous executives.

"Don’t call me that word," Scorpio says. "I don’t like things that elevate me above the other people. I’m just like you. Aw, sure, I come later in the day, I get paid a lot more, and I take longer vacations, but I don’t like the word ‘boss.’"

Then, after showing Homer the moccasins he’s wearing and saying that there’s a pair waiting for him in the closet, he takes off the shoes, throws them out the door, and asks Homer if he’s ever seen a guy say goodbye to a shoe. "Yes, once," Homer replies. In a testament to the obsessive nature of Simpsons fandom (and to Sayre’s law), the throwaway exchange has sparked one of the most heated and least important debates in history.

Some believe that Homer is talking about what he’d just seen. Others are sure that Homer is referring to a different guy he once saw saying goodbye to a shoe. A recent BuzzFeed poll conducted about the meaning of the line collected 109,000 votes. The interest generated by the dispute is further proof that if necessary for survival, the internet could subsist solely on Simpsons minutiae. (In fact, Jonah Peretti practically built BuzzFeed on this sort of ephemera, a Scorpioesque feat in itself.)

So was Homer thinking about the present or the past?

"I probably thought it was a previous time," Castellaneta, who improvised the line, told BuzzFeed, "but it is funnier if it means he saw it at that moment." Weinstein concurred: "He’s referring to something in the past. It would take too many mental moves and twists for the joke to be that he’s referring to what Hank Scorpio just did."

Homer’s reminiscence of shoe-throwing aside, he’s smitten with his new boss. During one moment of bonding, Homer tells Scorpio about his lifelong dream to own the Dallas Cowboys. And when Homer needs hammocks for his tired, overworked employees, an elated Scorpio suggests several different stores, including the Hammock Hut and Put Your Butt There. To Homer, who’d worked for a vampiric plutocrat for his entire professional life, all of this is a revelation.

"Predominantly in our mind, he was like a Steve Jobs–type guy," Weinstein said of Scorpio. "I don’t think we knew at the time Steve Jobs’s dark side. This new-style boss, as opposed to Mr. Burns, treats Homer with respect. And because Homer’s treated with respect, he treats his employees well."

What Homer doesn’t realize is that his employees are working on a nuclear generator for Scorpio, who’s a doomsday-device-possessing supervillain. He even has a cavernous lair that Homer walks right into when he’s looking for sugar for his coffee. (Scorpio scoops some out of his pockets. When he offers cream, Homer declines.) Later, as Homer tries to feed a dollar bill into a vending machine — Anderson says the gag was rooted in experiences Simpsons employees had with a similarly stubborn soft drink dispenser — he doesn’t even notice that Scorpio is using a laser to try to kill a copyright-free spy named James Bont.

While Homer is helping a megalomaniac, the Simpsons become disillusioned with Cypress Creek. Because Bart doesn’t know multiplication or how to write in cursive, he’s thrown into his new school’s remedial "leg-up" program. Depressed that the family’s sparkling, fully automated home has eliminated the need for her to do chores, Marge starts drinking a glass of wine each day. The town’s plant life betrays Lisa, causing her to have a severe allergic reaction. (Daniels put that idea in his original episode treatment after researching Austin, Texas, which can be a hellish place for allergy sufferers.) In the final act of "You Only Move Twice," Marge, Bart, and Lisa tell Homer that they want to go back to Springfield, which — despite its perpetual tire fire and three-eyed fish — has a soul.

In the episode’s elaborate climax, Homer slumps into his boss’s hideout and quits. As Homer is breaking the news, Scorpio and his lackeys are busy fighting government troops. It’s a scene straight out of a Bond movie. "On your way out, if you want to kill somebody," Scorpio tells him while saying goodbye, "it would help me a lot." The last we see of the most gregarious, violent billionaire on earth, he’s laughing maniacally and firing what Anderson said is a flamethrower modeled after the one Ripley uses in the Alien movies.

For Homer and the audience, it’s a surprisingly poignant moment. "He finds a guy who seems super nice and he has to give it up for his family," Daniels said, "which is just sort of a sad, little emotional story."

As soon as the Simpsons return to Springfield, Scorpio sends Homer a bittersweet surprise present: an NFL franchise. But like fellow tech bro Mark Cuban did with the Mavericks, Scorpio buys low. The writers originally had Scorpio gifting Homer the mediocre Houston Oilers, who didn’t have nearly the cultural cachet of the other club in Texas. But the Oilers had just announced that they were moving to Nashville. Instead, the writers ended up going with George Meyer’s favorite team: the Denver Broncos. "It’s not the Dallas Cowboys," Scorpio’s telegram to Homer reads, "but it’s a start." With the full squad assembled on the Simpsons’ front lawn — a player wearing John Elway’s number inexplicably goes out for a pass and falls down — Homer explains his disappointment to his wife with this memorably doltish line: "You just don’t understand football, Marge."

Back then, the Broncos were mostly known for losing Super Bowls. A season later, in yet another sign that The Simpsons was ahead of its time, Denver won its first championship.

When production of "You Only Move Twice" finished, Anderson said that then–Simpsons creative consultant and future Pixar director Brad Bird screened the episode and liked what he saw. "I’m not sure this show should work," Anderson remembered him commenting, "but it sure does."

In other words, it somehow manages to combine family drama, absurdist humor, and thumping action without coming off as too ridiculous. It’s one of the best episodes in the 27-year history of a show that, at its peak, regularly churned out multilayered classics. (Hardcore fans seem to agree. Paul Kehrer, a software developer and cofounder of searchable Simpsons database Frinkiac, told me that by the number of GIFs created, "You Only Move Twice" is the site’s sixth-most-popular episode.)

To this day, Hank Scorpio is beloved. During the development of The Simpsons Movie, there was a short stretch when the producers considered resurrecting him as the villain before wisely deciding against it. At a Simpsons Comic-Con panel last year, longtime producer Al Jean said that Scorpio was "the most asked-for character that we’ve had." The problem with bringing him back, however, is the same thing that made him great: Albert Brooks improvised Scorpio’s best lines. It’s impossible to re-create a one-of-a-kind piece of art.

"People always ask, ‘Are you doing Hank Scorpio again?’" said Anderson, who’s now The Simpsons’ supervising director. His response is always the same: "No, no, we’re not doing it."

It’s too bad, really. Modern-day rich guys are becoming more like Scorpio by the day. Don’t believe me? Amazon founder Jeff Bezos started a company that builds space rockets. SpaceX CEO Elon Musk just announced plans to colonize Mars.

"They could very well be future Scorpios," Weinstein said. "It’s really true. And it’s their choice to go evil or not."

Alan Siegel is a writer in Washington, D.C. Email him at asiegel05@gmail.com and follow him on Twitter @AlanSiegelDC.