There is no shame in a powerful tyrant or boss in video games requiring a second-in-command. After all, they need recreational time to sit in their world-domination chairs and ominously stare at the protagonists' progress while the henchmen deal with them. It just so happens that with all the fighting and experience the henchmen have been gaining, they have become better than their bosses.
If not in terms of power, then they definitely deserve the crown better either due to their charisma or how close they are to transcending into an antihero. The irony is that these following video game henchmen have overshadowed their bosses either in power, popularity, or just plain coolness. They ought to just resign and become their own boss, and some of them did.
8 Vaas Montenegro – Far Cry 3
As far as Far Cry villains go, Vaas Montenegro ranks high up based on charisma alone. Hoyt was always the original main villain in Far Cry 3 but the developers were so entranced with actor Michael Mando's audition performance that they wedged in a villain specifically to accommodate all that raw talent. That villain was Vaas.
In any case, Vaas was in many ways superior to Hoyt. So much so that when Vaas died halfway through the story, the game lost its soul. He was always an enigmatic, crazed maniac that terrorized and toyed with the protagonist both physically and psychologically. Yet there is a lot more depth to his insanity than just stereotypical evil. And there's also the fact that he gets his hands dirty on the ground, making him a much more involved commander.
7 Arthur Morgan – Red Dead Redemption 2
As criminals in the wild west, there's no doubt that Dutch van der Linde's outlaw gang in Red Dead Redemption 2 was villainous from a certain perspective. Those who have played the first game are well aware that Dutch will descend into hypocrisy and megalomania and the prequel game portrayed this gradual fall.
Thus, for most of the prequel, Arthur Morgan has always been the better man despite merely being Dutch's main muscle. Arthur at least kept to the virtues that Dutch taught him and held his sense of justice and fairness high. His genuine sympathy for the Native Americans and opposition to Dutch's needless murder sprees made him worthy of being the gang leader more so than his boss.
6 Shadow The Hedgehog – Sonic The Hedgehog games
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Shadow the Hedgehog was initially Dr. Eggman's ace in his fight against Sonic for world domination. But seeing as he's cooler and has a better hairstyle than the evil genius scientist who keeps losing to a blue hedgehog, there's just no way he would continue working with Eggman.
So eventually, he betrayed Dr. Eggman after some realizations and helped thwart some hidden doomsday plans concocted by his original creator. While Dr. Eggman has always been Sonic's arch-nemesis, Shadow provides the much-needed mirror image and exploration of what Sonic would have been if he was a bit more evil.
5 Starkiller – Star Wars: The Force Unleashed
Starkiller or Galen Marek is a Jedi everyman introduced in Star Wars: The Force Unleashed in its own pocket of canon in the Star Wars continuity. Supposedly, he was being groomed as a secret apprentice for Darth Vader and was thus trained from youth as a Sith warrior until he became disillusioned and rebelled against the Emperor.
As a force-sensitive being, Starkiller was a handful, even for standard Star Wars lore. His most amazing feat was telekinetically crushing a whole Star Destroyer vessel with nothing but the Force and a few strained veins. Those things are the aircraft carriers of the Star Wars mythos. Suffice it to say, he is someone who could take on Vader and Sidious based on potential alone.
4 Tommy Vercetti – Grand Theft Auto: Vice City
Just about any GTA protagonist can fit in here, but among them, Tommy Vercetti from Grand Theft Auto: Vice City displayed the most guts after betraying several of his bosses directly and starting some kind of organized crime coup. At first, he was just a drug deal delivery boy who was set up in Vice City and then had to work freelance for another crime boss.
He betrayed the local top-dog crime boss in Vice City so he could take over the business, thus also betraying his original Mafioso boss back in Liberty City, resulting in a bloody urban war. Tommy came out on top despite all the stacked odds against him. For a henchman, that's more than an impressive climb to the top.
3 Revolver Ocelot – Metal Gear Solid Franchise
Speaking of henchmen betraying multiple bosses, Ocelot from the Metal Gear games has quite the curriculum vitae. He's known as being a double, triple, or even quadruple agent, serving on multiple sides to further his agenda. It just so happens that his agenda is prolonging warfare or ensuring there's no shortage of war so he never runs out of gigs.
It takes a special kind of guile and mental gymnastics to pull that off without going mad, and Ocelot did go mad. But that doesn't mean he's no less clever or deadly than the bosses he once served. Ocelot outlived many of his former employers, after all.
2 The Turks – Final Fantasy 7
The Turks from Final Fantasy 7 are tasked with serving Shinra's interests. The latter is a power-hungry power company whose policies and profit-grabbing resulted in planetary harm and devastation. One would think that Shinra's henchmen would be deplorable and boring suits, but The Turks are pretty decent despite their employer's philosophies.
For one, they have no qualms about working with the very freedom fighters and rebels that their employers hate if it meant serving and saving someone or something. These fan-favorite henchmen are also pretty laid-back for people working in a cutthroat corporate environment. To that end, they're definitely better (at least morally) compared to their bosses.
1 Arthas Menethil – Warcraft Franchise
If there was one henchman whose climb was even more impressive than Tommy from Vice City, then it would be Prince Arthas from Warcraft lore. He started off as a firebrand prince whose extreme devotion to justice led to his being corrupted by the Lich King and serving the Burning Legion. This evil reversal marks the start of Arthas' henchman days as the Lich King's Champion.
Eventually, he realized what he'd been missing out on and knew that he could take the Lich King's power for himself. The bonus goal was to also sever his toxic employment with the Burning Legion. Arthas did so with flying colors, leaving a trail of dead demon, elf, and mortal corpses in his wake. All that for a used crown and a Frozen Throne.