It’s bound to happen sooner or later; not every good guy can stay good forever. Or, in some cases, even very long at all. Look at Red Mist (Christopher Mintz-Plasse) in Kick-Ass. He was the son of a villain who genuinely wanted to do good… until his dad gets killed, that is. Now he’s all baddie (named Motherfucker) in Kick-Ass 2. This got us thinking – which are the best, or most shocking, transformations of good guy into bad guy? Which are the ones that made our mouths drop open or spit out the beverage of our choice? Here are a list of ten, a top ten, you might say. (Read with caution, there be spoilers if you’re way behind on things.)

Hal Jordan (AKA Parallax) – Green Lantern
He was the best Green Lantern of the bunch, and a true blue (or green) asset to the Justice League for decades, but even the most pure can be corrupted. For Hal, the Silver Age GL, it took the destruction of his beloved Coast City by that psycho-Cyborg-Superman, Hank Henshaw, to start the evil ball rolling. After an argument with the Guardians, who accused him of using his powers for personal gain, Hal decided to slaughter all of the Lanterns (even Kilowog!); eventually he absorbs all the power in the central battery and emerges Parallax. Sad and shocking in equal measure.

Anakin Skywalker (AKA Darth Vader) – Star Wars
This one isn’t quite the same since we knew Darth Vader was a bad guy, but in The Empire Strikes Back, when he reveals to Luke that HE is his father, the kind and noble Jedi Obi-Wan had told him about, Luke and the audience were sufficiently gobsmacked. The prequels and spinoff media show us the downfall of the once-great Jedi who became seduced and overtaken by the Dark Side. Man, that Dark Side’ll get you every time.

Jean Grey (AKA Dark Phoenix) – X-Men
Here’s another case of a hero, one of the purest of them all, being overtaken by a greater malevolent entity. Jean Grey’s telekinetic and psychic abilities expanded exponentially when she was exposed to fatal levels of radiation trying to help the other X-Men land their space shuttle safely. When she resurfaced, she was not merely Jean Grey; she was the Phoenix! This power is too much for her, though, and she lets the bad in when the Dark Phoenix casually causes the death of billions by eating a star. Not good times, there, Jean.

Capt. Jean-Luc Picard (AKA Locutus of Borg) – Star Trek: The Next Generation
Talk about a punch to the gut! By the end of the third season of TNG, the Enterprise had faced the Borg a few times and, while irritating, they never proved to be the enormous threat they became. That all changed in the season finale, “The Best of Both Worlds,” which had the mechanical hive abduct the beloved and peaceful Capt. Picard and assimilate him into the collective as the laser-pointer-faced Locutus. Sure, he got un-assimilated in the season four premiere, but there were months of sheer panic on the part of fans. Bedlam, you guys.

Bucky Barnes (AKA The Winter Soldier) – Captain America
He wasn’t the first sidekick to go down the dark path, but few were as squeaky clean as Captain America’s faithful masked and be-tuniced chum Bucky Barnes. While attempting to defuse a bomb planted by the evil Baron Zemo during WWII, Bucky is blown up, saving thousands of lives but apparently dying himself. OR SO WE THOUGHT. He is evidently saved from death and put into a series of suspended-animation comas in between which is he made to do a lot of bad things for bad people. And his hair got way more rock star.

Angel (AKA Angelus) – Buffy the Vampire Slayer
We’d always heard about how bad the vampire with a soul used to be prior to his gypsy curse, but boy howdy, were we unprepared. After getting a little TOO happy with Buffy, Angel’s soul is stripped away and he reverts to the sadistic Angelus about halfway through the second season. To say that things get real bad is an understatement as it becomes Murder Buffy’s Friends Time. This causes her to paraphrase Jim Gaffigan: “I can’t believe my boyfriend turned evil after sex on my birthday.”

Adrian Veidt (AKA Ozymandias) – Watchmen
Now, we can never truly be sure how long the smartest man on Earth had been doing bad things, but we can certainly tell you it was a lot longer than Rorschach and Nite Owl thought. As the least involved member of the group, in retrospect he seemed like the obvious candidate to be the baddie (made more obvious in the film), but we were still pretty aghast when the revelation hits our “heroes” like a ton of pseudo-alien guts that Veidt was willing to sacrifice millions to ensure peace. When do the ends justify the means? Why was Bubastis in the movie?

Rhinox (AKA Tankor) – Transformers: Beast Wars & Beast Machines
What’s worse: thinking a dear friend and comrade is dead or finding out he’s actually an evil person? Or robot in disguise, in this case. The saddest (and weirdest) thing about this fall from grace is it actually happened offscreen in between series. Beast Wars ended on a cliffhanger and when Beast Machines began, they were back on Cybertron and everything was different. Rhinox, the backbone of the Maximals, was gone, seemingly forever. Eventually, it’s discovered that he’d been turned into an evil Vehicon named Tankor, the scourge of good things. Unlike Silverbolt, though, who’d been turned into Jetstorm, Tankor didn’t want to be good again. Cold, Megatron.

Jason Todd (AKA Robin, AKA Red Hood) – Batman
We really have no one to blame but ourselves. Jason Todd was the second Robin in the early-80s and he had a hard time filling Dick Grayson’s green booties, both on the page and with fans. DC put it to a vote to decide Todd’s fate and overwhelmingly, the decision was made to off the youngster. In 2005, he resurfaced as the villain Red Hood, who was understandably miffed that he’d been left for dead by his supposed friend and mentor, Batman, who was taken aback all the way to Hackensack.

Rassilon (AKA The Narrator) – Doctor Who
For a long while, we’d heard rumblings of Rassilon, one of the oldest and most powerful of the Time Lords. He and Omega invented the process that allowed Gallifreyans to travel through time, even, and he was known to have many items that people could find and use for various ceremonies and things, the best being “The Rod of Rassilon” because it sounds the dirtiest. However, when we saw him (portrayed by Timothy Dalton) in “The End of Time,” having been brought back to life to fight in the Time War, he had clearly lost his mind and now thought destroying Earth to ensure his own survival was plenty okay. It wasn’t, of course. Also, that episode is dumb.

Surely we missed some of your favorite or most heartbreaking. Let us know what you think in the comments below.