Thanks to S.J. Edwards, Elizabeth Bear, DJ Chaotica, Larry-Bob Roberts, Zack Stentz, Daphne Gottlieb, Paul McEnery, James McGirk, Jessy Randall, Kevin Schmidt, Morgan Johnson, Susie Kay, Kat Page and David Fraser for the suggestions!

The Mayor In City Of Ember
He's the textbook example of a corrupt mayor who's only interested in saving his own skin. He knows the underground city of Ember is on its way out, and soon it'll be uninhabitable due to power failures and dwindling supplies. But instead of trying to cope with the problem, the mayor tries to hoard as much stuff for himself as possible, in a secret room — and puts together meaningless commissions to study the problem. Here he is in this video, eating sardines in the grossest possible manner.

Lando Calrissian in Star Wars: The Empire Strikes Back
Okay, so Lando is the kind of scoundrel we love to watch. And he's a perfect counterpart for Han Solo. But would you really want him in charge of your city? His Cloud City of Bespin seems like a pretty corrupt, messed-up place. And then he goes inviting Darth Vader and his crew there, which is not good city planning at all. And then after Vader has demolished half the city in his battle with Luke Skywalker, Lando takes off and leaves his city behind. Call that leadership?

Aunty Entity in Mad Max: Beyond Thunderdome
She does keep the city of Bartertown humming along — except when she gets stuck into an idiotic power struggle with Master/Blaster, and everything grinds to a halt. Plus she rules with an iron fist, and forces people to fight to the death in a deadly arena. That's not the kind of leadership our post-apocalyptic cities need!

Mayor in RoboCop 2
He makes deals with drug dealers and criminals. And then he mismanages the city's finances and winds up handing the entire city over to the evil OCP. This clip pretty much says it all. And when he's in a tight corner, he just loses his shit.

Mayor Wilkins, in Buffy The Vampire Slayer, season 3
Your average terrible mayor may let the city fall apart, or make deals with drug lords, or bulldoze your house for no reason. But a really awful mayor, like Wilkins, makes cozy arrangements with vampires and tries to kill off the town's only protector. And then tries to turn into a demon so he can eat the high-school graduating class. Now that's bad leadership.

Vilos Cohaagen, in Total Recall.
He's an evil administrator of the Mars settlement, keeping the mutants down and ruling with an iron grip. He uses mind-control and brainwashing to keep his minions in line. And worst of all, he won't give the people air. WTF, Cohaagen?

Mayor Bentham Rudgutter, in Perdido Street Station by China Miéville.
He's always described as sitting "regally on his throne," or sitting "behind his desk with an air of utter command." He rules over New Crobuson, with its corruption and oppression — and he's not averse to making deals with the city's crime syndicates as well as its demons. He systematically rounds up dissidents and has them tortured, and he's not above imposing martial law if the situation gets out of hand.

Father in Equilibrium
Father rules over the city-state of Libria and outlaws all human emotion, even the love of a small puppy. To this end, he keeps the people doped up on a drug called Prozium, and keeps everyone under constant surveillance. (Similar to other figureheads like Big Brother in 1984, or Mustapha Mond in Brave New World — except that Father just rules over one city.) The only good thing "Father" has going for him is his kick-ass gun-centric martial art, gun-kata. Woo hoo!

Judge Cal, In Judge Dredd
This character, closely based on the Roman emperor Caligula, seized power after he had the Chief Judge of Mega-City One assassinated. In Mega-City One, the Chief Judge has absolute authority — an arrangement that's caused some problems on several occasions. So Judge Cal goes completely nuts, making it a crime to criticize him and appointing a goldfish as his deputy. He even shoots Judge Dredd! Dude!

Mayor Prentiss in The Knife Of Never Letting Go by Patrick Ness.
Prentisstown is not a nice place to begin with — there are no women, and the males can all hear each other's thoughts all the time, whether they want to or not. But Mayor Prentiss makes matters worse, by figuring out a way to control men's minds. He declares himself President and invades the neighboring settlement of Haven, where there are some women. And that's just the beginning of his reign of terror. Runner up: The mayors in Truancy by Isamu Fukui.

5. Sun of Suns, by Karl Schroeder. Rebel, former pirate, and kickass airbike rider Hayden lives in Virga, a giant bag of air floating in space, built by a post-human society. The air is heated by high-tech suns dragged around by city-states that create their own gravity by building on the inside of vast, spinning tubes. Virga is a kind of eighteenth-century world of kings, despots and pirates, and many of the city-states horde sun power — they'll attack out any nation that tries to assert independence by building its own sun. Most people remain dependent on a few big sun-owning nations for their warmth; those who refuse to toe the line live in the cloud-draped sunless reaches of "winter." Hayden, whose mother was killed after she built a pirate sun, is out to change all that, even if it means killing the leader of Slipstream, one of Virga's most powerful nations. The characters may be a little two-dimensional, but you'll keep reading just to visit the vast, globular floating oceans, the strange cities, and bizarre barren outposts in Virga. Plus, pirate battles in zero gee! Sun of Suns is the first in a trilogy, and the second novel just came out in hardback.

4. Ringworld, by Larry Niven. A classic 1960s world-building epic about aliens on a quest to find out more about a vast artificial Dyson ring built around a dying sun. This is the novel that inspired the people who created the game Halo, which also takes place on a ring world. Expect strange weather, bizarre vistas from on and below the massive structure, and alien encounters that feel very Star Trek (but at a time when Star Trek was still the shit).

3. Lilith's Brood, by Octavia Butler. This trilogy of novels by MacArthur winner Octavia Butler is about what happens to humanity after earth is destroyed in some kind of nuclear apocalypse, and all the human survivors are rescued by powerful, mysterious aliens called the Oankali. Three-sexed, the Oankali reproduce via a third sex called the TK, which mixes genetic material inside its own body and creates offspring. All their technology is biological too. Lilith, one of the human survivors that the Oankali enlist to help them deal with the other human survivors, discovers that the Oankali recreate their species every few hundred years by merging their genetic material with other species. And the humans are next on their list of species to merge with. Set aboard vast biological ship-words and a newly geo-engineered Earth, Lilith's Brood traces three generations of humans and Oankali as they have children together — children who grow more alien to both species with each generation. Yes, it's a very complicated and subtle allegory about colonialism. And yes, it's an amazing tale of the unknown. Enjoy it for either, or for both.

2. Perdido Street Station, by China Mieville. It's a world where bureaucrats raise demons with steam-driven machines, and "thaumaturgists" remold human bodies with their hands. A strange kind of species-transforming weather called The Torque occasionally rips through, converting humans into half-insects, half-birds, half-seamonsters. It's been years since a Torque came through, and all the different post-Torque human groups live separated into nineteenth-century style ghettos in a city whose polyglot heart is in a train station called Perdido Street. Everything is steaming along normally in the city — anarchists print subversive pamphlets, artists date across species lines, and scientists study winged creatures from around the globe. But trouble comes to town in the form of dream-eating moths who suck people's minds out, and the only creatures who can stop them are a mad scientist, his half-insect lover, a sentient garbage dump, and a trans-dimensional spider.

5. The Dispossessed, by Ursula LeGuin. A classic novel by one of the supreme world-builders in SF, The Dispossessed is a tale of two planets: one is a lush, economic powerhouse ruled by greed, consumerism, and a rich elite; the other a desert planet full of the descendants of rebels who fled the first planet two centuries before. It has scant resources but is governed by a feminist-anarchist belief system that preaches collective ownership, gender equality, and sexual liberation. Shavek, a physicist from the anarchist planet, is one of the first to visit the home planet in many generations, and his experiences traveling between worlds reveal chinks in the Utopia he's left behind — and unexpected benefits on the corrupt home world, where scientific innovation flourishes in an atmosphere of capitalist competition. What's stunning about this novel is that LeGuin avoids simplistic judgments, and shows in honest detail how even the most progressive culture can be corrupt. And even the most corrupt culture can foster creative brilliance.