Set roughly two decades after the events of the Oscar-winning first film, Gladiator II tells a new tale about the Roman Empire and those who dared to defy it. Ridley Scott’s original film featured two Roman emperors, one good (Marcus Aurelius) and one very bad (Commodus); likewise, Gladiator II also features a pair of real-life emperors, only this time both fit most clearly into the villain category. As played by Joseph Quinn and Fred Hechinger, respectively, Geta and Caracalla are twin brothers whose reign as co-emperors is marked by cruelty, corruption, and chaos.

“Their bloodthirsty whims and equally unpredictable mood swings make this nightmarish pair of little freak boys worthy successors to Joaquin Phoenix’s supremely simpering Commodus. Their antics border on slapstick, but Quinn and Hechinger are each so temperamental and off-putting that they never let you forget the danger Geta and Caracalla pose to Rome’s future,” wrote IGN’s Tom Jorgensen in his Gladiator II review.

Geta and Caracalla, however, are just the latest in a long line of wicked emperors to grace the screen. Indeed, evil emperors – some real, some fictional – have long been the villains that the forces of freedom must overcome in movies, video games, TV, literature, and comics.

Here are the 10 best worst emperors that pop culture has yielded thus far, starting with …

Caligula

This 1979 Italian cult classic stars Malcolm McDowell (A Clockwork Orange) as the titular young Roman who assumes control of an empire in decline and, by the film’s end, has grown mad in his quest to destroy and humiliate Rome’s ruling political class. Depravity and corruption abound in this erotic production from Bob Guccione, founder of Penthouse magazine, who added hardcore sex scenes in post-production. Stalwarts of the British stage and screen like Helen Mirren, Peter O’Toole, and John Gielgud round out an ensemble far too classy for this notoriously crass affair.

Commodus

Another real-life Roman emperor, Commodus, the demented son of the esteemed Marcus Aurelius, was portrayed by Christopher Plummer in 1964’s The Fall of the Roman Empire and, more famously, by Joaquin Phoenix in 2000’s Gladiator. Phoenix plays Commodus as murderously jealous of his father’s most loyal general and surrogate son Maximus. After Commodus kills Marcus, Maximus goes on an epic journey that sees him become a gladiator out for revenge against now Emperor Commodus. Ridley Scott’s sumptuous sword & sandal epic not only vividly recreates Ancient Rome but, through Phoenix’s Oscar-nominated performance, further seared the image of the thumbs-down, mad emperor in the public imagination.

Doctor Doom

Already the monarch of the fictitious nation of Latveria, Marvel’s greatest supervillain is poised to get promoted next year in Marvel Comics’ crossover event The Rise of Emperor Doom. The synopsis for the storyline suggests some of Earth’s heroes wonder if the world isn’t better off under Doom’s control. This won’t be the first time Doom has become an emperor, mind you. In 2015’s Secret Wars, he became God Emperor Doom after stealing the Beyonders’ powers.

Han

Jet Li starred in The Mummy: Tomb of the Dragon Emperor as the titular villain, a fictionalized version of the founder of China. In the film, the third and final entry in the Brendan Fraser-led franchise, the vicious tyrant Qin Han conquers ancient China, builds the Great Wall and gains supernatural power over the elements. He is later cursed, and he and his soldiers turn into terracotta statues. Han is resurrected centuries later and resumes his conquering ways only to meet his end at the hands of plucky adventurer Rick O’Connell and his pals.

Joker

In Jeph Loeb’s Superman: Emperor Joker, the Clown Prince of Crime tricks fifth-dimensional being Mister Mxyzptlk into giving him nearly all of his reality-bending powers. The now-omnipotent Bat-villain uses them to warp existence into an absurdly hellish realm where he can do anything from repeatedly killing Batman and Lex Luthor to consuming the population of China. The Emperor Joker story was later adapted for an episode of the animated series Batman: The Brave And The Bold.

Leto II

While Padishah Emperor Shaddam Corrino IV might be more widely known to general audiences through his depictions in David Lynch and Denis Villeneuve’s respective Dune movies, we’re opting to include a far stranger character from that franchise on this list. The son of Paul Atreides and his Fremen concubine Chani, Leto II eventually became known as the God Emperor of Dune. Like his aunt Alia, Leto II is a pre-born (deemed by the Bene Geserit as abominations) who possesses the memories of his ancestors. He ultimately undergoes a ritualistic test, consuming vast quantities of spice melange, and, over centuries, transforms into a human-sandworm hybrid.

As emperor, he ruled the universe for over 3,500 years, following the Golden Path that necessitates he serve as a divine tyrant so that humanity eventually learns that it must not succumb to charismatic leaders if it’s to survive and thrive. Yeah, it’s all really weird but ultimately the point is that Leto II let himself become a literal monster emperor in order for humans to finally get their shit together. So yay? James McAvoy played a pre-sandworm Leto II in the TV miniseries Frank Herbert’s Children of Dune.

Ming the Merciless

Over decades of appearances in comic strips, serials, TV, and in film (most famously played by Max von Sydow in the 1980 cult classic), the intergalactic despot Ming the Merciless rules the planet Mongo with an iron fist. For the most part, Ming made the conquest of Earth and the enslavement and punishment of the citizens of Mongo his top goals, but was steadfastly resisted by the heroic human Flash Gordon and his allies at every turn.

Palpatine

One of cinema’s best-known villains, Star Wars’ Sheev Palpatine was a member of the Galactic Senate who, in fact, was also the dark lord of the Sith known as Darth Sidious. He corrupted the Jedi Anakin Skywalker, eventually turning him into his protege and top enforcer Darth Vader. Palpatine engineered the downfall of the Senate and established the Galactic Empire with himself as ruler. The Rebel Alliance eventually defeated and seemingly killed the Emperor at the Battle of Endor … only to find out decades later “somehow Palpatine returned.” This time, Palpatine’s Jedi granddaughter Rey finished the job Luke Skywalker and friends had started.

Shao Kahn

This iconic Mortal Kombat baddie is the Emperor of Outworld and the archenemy of Raiden. A cruel, highly intelligent and god-like tyrant with the power to absorb souls, Shao Kahn’s prowess in the dark arts aids him as a combatant but his arrogance has cost him many victories, especially in his quest to conquer Earth. In addition to being a fixture of the Mortal Kombat game franchise, Shao Kahn has also appeared in live-action in film and TV adaptations.

Zurg

Buzz Lightyear’s archenemy, Zurg is the Toy Story franchise’s riff on Darth Vader. Zurg is out to conquer the universe with only the heroic Star Command standing in his way. A towering, armored figure, the movie Lightyear revealed a shocking backstory for Zurg that put a major twist on the relationship between the Pixar franchise’s space-faring hero and his chief foe.

For more evil emperors, check out IGN’s Gladiator II review and our Gladiator II ending explained.