...and the one that's desperately trying to break free is Raphael.
Leonardo
Archetype: The Mediator. Introvert, relationship oriented. Leonardo is like Water, the most calm, relaxed, and unemotional personality. He's the Marge Simpson of the group, the even-keeled peacekeeper whom often acts as the glue that holds the group together.
1987: This Leo was like the charming Superhero type. He's a very competent leader, so much so that when he decided to give up on being the leader, none of the other turtles could work together until he came back. He was always helpful and always wanted to do good things, was a dedicated student of the martial arts, etc.
2003: Leo here was very serious, look at how serious he is you guys, and is constantly focused on his training for fear of being too weak to protect his loved ones. Though he wasn't stoic all the time, there were times when he could make jokes and have some fun.
2012: This Leo felt like an attempt to characterize him more like an actual teenager, sometimes he could be a little bit of a jerk, but it's understandable when your brothers don't listen to you. Later on he undergoes massive character growth and truly becomes a competent leader, like having lead them into space without Splinter, etc.
2018: It hasn't gone unnoticed that pretty much all the Blue characters Ben Schwartz have voiced are incredibly similar, be that his version of Sonic the Hedgehog, or Dewey from modern Duck Tales. Leo in this is almost the complete opposite from previous iterations, he's laid back and rarely takes anything seriously, and he likes it that way. He is shown numerous times that he has what it takes to be the leader, but is just too lazy.
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The reason 2012 wins is because we constantly have to see Leo grow into a competent leader. Especially after Splinter is gone for good, now he has to step up even more and becomes the person his brothers depend upon. This is the closest to what I'm looking for when it comes to Leonardo, he can be as by-the-book as he wants in the beginning, but eventually you do want to see him come into his own and the difficult journey he goes on in order to become that.
Donatello
Archetype: The Thinker. Introvert, task oriented. Donatello is like Earth, the most moody, philosophical, and withdrawn personality. He's the Lisa Simpson of the group, the detail oriented planner who lives inside their own head and tends to be the group's problem solver.
1987 and 2003: The thing about the original and "Don" is that he changes the least upon transitioning into the new show. The main difference is that 1987 wanted to be accepted by the whole world for his knowledge, while 2003 didn't, he's just looking to expand his knowledge to help his brothers. 1987 would make some outlandish inventions, while 2003's were more believable and they always worked.
2012: Donnie this time was very eccentric, excitable, socially awkward and fully in love with April. He also had a bit of a temper at times and bickers with his brothers when they don't respect his intellect, which can be irritating.
2018: Donnie here is cocky about his tech abilities, obsessed with working on tech, is a massive adrenaline junkie and loves to dance. He has a jetpack and his futuristic Bo Staff can do many badass things. This is the funniest iteration, though he can be overbearing and a jerk at times.
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This was tough because there doesn't seem to be any horrible Donnie's, but I've decided to give 2018 the win for the time being. This one was the most memorable, the most enjoyable, and benefits the most by going all in on the faux-anime bullshit. His Tech-Bo alone is genius.
Raphael
Archetype: The Hothead. Extrovert, task oriented. Raphael is like Fire, the most bold, courageous, and audacious personality. He's the Homer Simpson of the group, whom tends to be the most aggressive, throwing themselves into big situations.
1987: I'm going to be completely honest here, this Raph has got no chance at winning. He's still cynical, sure, but he's comedic with it. And he's honestly very similar to Mikey, is constantly breaking the fourth wall, and has some of the best one-liners. At times he came across as really lazy and didn't like fighting, so no, that's weird, get outta here.
2003: Come on, this guy's a badass. He loves to fight and is constantly training to get stronger. I felt that his tough Brooklyn accent really suited this iteration. He also had berserker rage at moments which could get him into trouble, and although later he did mellow out, he always still enjoyed a good fight.
2012: This Raph is one of the strongest fighters and is a great asset to the team, though he is a smart-ass and a bit cocky. He also had berserker rage at moments and needed his brothers to calm him down. He can be a bit of a bully at times, picking on his brothers, though he does grow as a character and becomes more likeable as the series goes on. He's scared of bugs.
2018: Raph was made the leader in this iteration and while I'm not fond of that idea, it does make sense in this specific instance. He's not the angry one and isn't even all that rude, he's just a very kind older brother who just so happens to like smashing bad guys, eat, get rowdy, and work out. He tries too hard not to hurt people's feelings, and although he can be ignorant and goofy, he always means his best.
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The 2003 version wins without a doubt. I feel like he benefited the most from "look how cool we are now!" He's a freakin' badass, there's lots of pros, very little cons, and I don't think you can go wrong with this iteration of Raphael.
Michelangelo
Archetype: The Socializer. Extrovert, relationship oriented. Michelangelo is like Air, the most exuberant, enthusiastic, and outgoing personality. He's the Bart Simpson of the group, whom tends to talk a lot, and often comes with some degree of childlike wonder.
1987: This Mikey is incredibly likeable, so funny, and has a great surfer-dude accent. He had a tendency to be lazy and the most obsessive to pizza, but later on became more mellowed out and more of a competent team member. His only problem is they took his nunchucks away because they were deemed "too violent", now having to resort to his grappling hook.
2003: Mikey here was made to be one of the most competent fighters, he was creative and would talk so much his enemies could not concentrate. The problem here is he can come across as arrogant and too much of a try-hard sometimes, which can be irritating.
2012: Mikey is fun and likeable, a natural fighter and could move without thinking. The problem this time is he can come across as really stupid, like he always needs someone to hold his hand, though throughout the show he does become more mature, though still goofing around.
2018: This is your overbearing Mom's favourite Mikey, he's baby! He's optimistic, has a very kind heart at times, and is incredibly stupid. He can be chill and always looking to help where he can, but on the other hand he can be overly obnoxious, a huge jerk, and has insane anger issues when he is wronged, completely abandoning his nice guy demeanor if it meant getting revenge.
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The thing about certain characters is that they don't have to be all that deep, they just have to be charming, which is why the original 1987 iteration ended up winning for me. This Mikey remained likeable throughout and wasn't so irritating, which is all I really want or expect out of him.
So... there you have it! I feel like pitting the turtles against each other kind of highlights the strengths of each version, you think? Oh, and let me know who your favourite turtle is, I'd love to know.