Spartacus
"I Am Spartacus!" (Not Pictured: Spartacus)
While it's true that "gladiator" is probably one of the most badass professions this side of "ninja", "zamboni driver" and "t-shirt cannon operator", back in Roman times it wasn't all just dudes running around in skirts having fun and games at the old ball park and Russell Crowe's biceps - it was a tough fucking job, and the sheer nature of the profession meant that it had very few perks and a mortality rate that makes deep-sea Alaskan King Crab fishing look like a routine day at the pillow fluff inspection factory. Spending every afternoon holding a goddamn trident and trying to take on a pack of hungry charging rhinoceroses while being chained to a half-dozen sword-swinging virgin midget women solely for the viewing pleasure of a bunch of stuck-up rich snobs who'd like nothing more than to see you impaled on a rhino horn isn't really most peoples' idea of a satisfying career path. And back in Rome it's not like today where the prime super-stud athletes get six-digit salaries and live in giant mansions constructed out of gold and the crushed-up bones of orphan children where they spend all day counting the zeros in their bank account and nailing their bimbo wives who's fake boobs are so omega gigantor that their bra sizes can only be measured by NASA's top astrophysicists - no, the gladiators were essentially slaves who slept in cages, walked around in manacles, and who's only purpose in life was to kill other gladiators (and sometimes wild beasts) until such time as they themselves were killed in a violent and bloody way for the amusement of others. While that makes it a badass profession, it doesn't necessarily make it the sort of job that cares about shit like "employee satisfaction" and "worker morale". One guy who found this out the hard way was a dude known only as Spartacus.
Spartacus was a soldier from Thrace who served in the Roman Army's auxillary forces early in his life. He was tough as nails and fought well until one day when Rome was really getting their balls whipped and he decided to get the fuck away from the battlefield before a big angry German put a sword into his brain. Unfortunately back in those days the Roman Army didn't really understand the whole self-preservation thing. They labeled him a deserter, captured him, and sold both him and his wife into slavery. Because of Spartacus' natural strength and cunning, he was trained as a gladiator and shipped off to get busy hacking peoples' arms off and cracking rabid goats in the mouth with his fist. Well as I mentioned previously, the life of a gladiator wasn't exactly a walk in the park on a Sunday afternoon, so Spartacus was like, "fuck this bullshit" and decided to quit his job. And for Spartacus, "quitting your job" meant "liberating your wife, getting a group of about seventy hardcore gladiators, stealing a bunch of cleavers and knives from the mess hall, hacking up two dozen Roman soldiers and escaping off into the Italian countryside".
This is fucking gay, I'm outta here.
So Spartacus and his army of pissed-off gladiators took to the hills, plundering towns and raiding weapons stockpiles all over the place while the Roman Army stood around with it's thumb up it's collective ass. Soon other slaves, brigands, and outcasts in the countryside heard that there was this badass group of warriors fucking shit up, and they all wanted to get in on the action. Many other slaves overthrew their masters and ran off to seek glory with Spartacus, and before long the ranks of this rogue army climbed to an estimated 120,000 men, women, and children. Now the Romans obviously weren't too pleased about this rampaging horde of madmen tearing ass across their territory, so they sent the Praetor of Rome to bust Spartacus and his men up. About a month later the Praetor walked back into town alone. The gladiators had kicked his ass, killed all his men, and stolen his horse out from under him.
That was fucking it. The Romans sent both their Consuls out with two Legions apiece to deal with the Slave Army. However, they were unprepared for how balls-out a military strategist Spartacus was, and he and his gladiators had trained his peasants well. He charged the first Consul's army, kicked their asses, and quickly spun back to dish out another epic beat-down to the second army. After slapping four full Roman Legions around like they were insolent street prostitutes, Spartacus marched for Gaul, whipping the balls of another Roman Army while he was at it. Right when he was about to cross into Gaul and make a break for freedom though, he decided, "nah, fuck it" and turned around. He captured the town of Thurii and set up a camp there. The Romans tried to dislodge him once or twice, but were unsuccessful. For three fucking years Spartacus roamed the land kicking balls like AC Milan until finally the Roman noble Marcus Lycineus Crassus decided he was going to put an end to that shit. He put a force of eight full Legions together and managed to corner Spartacus' men in the toe of the Italian boot.
Spartacus attempted to break out through Crassus' lines, and at first his men fought several successful battles against the Roman Army. However, all the asskicking that the gladiators were doing finally made them a little too overconfident and despite Spartacus' orders they launched a full-on assault of Crassus' lines and suffered a crushing defeat. Contrary to what Kirk Douglas and Stanley Kubrick might have taught you, Spartacus was slain in combat on the field that day while trying to fight his way to Crassus and was not recaptured by the Romans. However, 6600 of his men threw down their weapons in surrender and were promptly crucified along the Appian Road outside of Rome. Crassus never gave the order for their bodies to be taken down, and the crosses remained for several years.
There's just something innately badass about a motherfucker who puts together an army of gladiators and hands the Roman Army it's ass time and time again. The guy's army of peasants and slaves was completely outclassed by the well-trained and better-equipped Romans, but through strategy and cunning he was able to whip his band of rejects into a fighting force that was able to hold it's own against Legion after Legion for three years. He liberated himself, fucked up the Romans, and died a free man. He gave no quarter, nor did he ask for it.
"Then pushing his way towards Crassus himself through many flying weapons and wounded men, he did not indeed reach him, but slew two centurions who fell upon him together. Finally, after his companions had taken to flight, he stood alone, surrounded by a multitude of foes, and was still defending himself when he was cut down."
- Plutarch, Life of Crassus 11:7