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Yeah, I suppose this is sort of cheating, plus its a day late. But really, I can't pick between them. I present to you:

Johan Liebert, Friend, and Pluto (image by Roymaru on DeviantArt).
Reads right to left.
Let's start with Friend of 20th Century Boys. Of the three, Friend is possibly the most mysterious. We get next to nothing certain about his past throughout the manga. Rather, Naoki Urasawa follows a group of children in flashback. We know that one of them is Friend. But we never find out who it actually is until the very last chapter, when Urasawa makes a reveal that is both suitably hinted at but completely surprising at the same time (I admit to being completely wrong in my guess). Friend's mysteriousness has an extra dividend: it makes him all the more inhuman, and thus scarier.
The problem with this (for someone trying to choose good scans) is this means he doesn't get as many good scenes as the other two. And when he does show up, it's usually something so completely story changing that I'd be spoiling far too much to use it. If I had to pick a good Friend moment, I'd take this rather out of context scan from Chapter 43:

Hopefully this conveys the childishness of the character without giving away too much. Note that "kun" is the Japanese honorific for a child.
Beyond having the coolest visual of the three (I like the mix of suit and mask), Friend's motivation is also interesting. While 20th Century Boys is, in a way, a love song to Urasawa's childhood, that type of nostalgia taken too far can be a bad thing. Friend is representative of that, a man willing to become a supervillain just so that the game of bad guys and good guys won't end. But dig a little deeper, and you find a dark void that can't be filled.
Johan is a similar beast to Friend in many ways. They both have mysterious pasts, they're both charismatic individuals who operate using agents, they're both driven by their own lack of humanity, and they're both willing to do pretty much anything to get what they want. While Friend where's a mask to hide his identity, Johan uses his boyish good looks and a tiny perpetual smile to avoid detection.
The difference comes down to the differences in the stories themselves. Monster's main theme is, simply stated, "No person is truly a monster." Johan, therefore, is much more human than Friend is, simply because exploring Johan's essential humanity is necessary to the theme of Monster, while similar questions are thrust aside in the case of Friend to preserve the mystery of 20th Century Boys.
This makes Johan both a better and a worse character than Friend. He's better, because we can explore him deeper and learn more about what drives him. He's worse, though, because he's stated to be something inhuman, but you can never quite feel that about him. He's a scary person, for sure, but he never reaches the heights of almost supernatural terror that Friend inspires.
Still, I have to say I like Johan more than Friend (despite preferring 20th Century Boys to Monster in general), simply because you do get those hints of something else going on inside him. He's a person who is trying to become a monster, and you wonder what drives him to doing that. Check out this scene where he confronts a would-be blackmailer while he's running his game on Schuvald (three and a half scans from Chapter 65):


This is where Johan succeeds where Friend fails. Friend merely scares me. Johan can do that (although not as well), but he also haunts me. Just try to disagree after seeing those eyes. Continuing on with the scene:


As I've mentioned earlier, Johan's nihilism is more powerful for its sincerity. He honestly doesn't care if he lives or dies. Can there be anything worse than being what he is? Johan's lack of concern over his safety is represented by one of my favourite recurring motifs in comics: pointing a finger at his forehead while a gunman threatens him. There are a number of variations on it, but it never quite seems to lose its power. I'd post them here, but this post is already running quite long. I may do another post with all of Johan's "shoot me" moments.
And finally, there is the powerful robot, Pluto. Pluto is different from the first two. While Johan and Friend are defined by their inhumanity, Pluto is a robot with too much humanity. This is an interesting subversion of the standard evil military robot story (including the original Astro Boy story "The Greatest Robot On Earth"). Usually the story goes something like "Robot is a weapon, doesn't want to be a weapon, learns to be more human, dies proving that it's no longer a threat." Pluto twists this around a bit: what happens when you teach a robot to love and then take away the object of its love? To answer that question, let's take a look at what the first appearance of Pluto in the very first chapter looks like, shall we?

"I hated her, so much... it-it- the f - it -flam - flames. Flames, on the side of my face, breathing-breathless- heaving breaths. Heaving breath..."
Joking aside, I'm actually strongly reminded of Munch's The Scream. Ignoring the more obvious similarity in the central figure, the colouration of the flames reminds me of Munch's famous sky and the whole painting style looks similar to me. It's also an interesting comparison in context: while The Scream represents a feeling of terror, "an infinite scream passing through nature", Pluto himself commands the forces of nature and is treated as one. Pluto, despite his own cry, is not the screaming figure from Munch's work, but the infinite rage and power that stalks that hapless person.
Pluto can't handle his humanity. He has the emotional maturity of an adolescent, and he the things he's been through have broken him horribly. His rage consumes him almost utterly, driving his actions beyond reason or pity. Ironically, this makes him strangely more effective than either Johan or Friend. While those two require intricate planning and psychological button pushing to spread their own inhumanity, Pluto merely has to give in to his own hate to breed more, as seen in this fight between Pluto and a revived Atom (three scans from Chapter 61):



And that's the grand link between the three. Johan and Friend's inhumanity, Pluto's hatred, they all attempt to infect those around them, in a misguided attempt to fight the original by becoming greater. Ultimately, the true test of the hero is not fighting the villain on his own terms.

Johan Liebert, Friend, and Pluto (image by Roymaru on DeviantArt).
Reads right to left.
Let's start with Friend of 20th Century Boys. Of the three, Friend is possibly the most mysterious. We get next to nothing certain about his past throughout the manga. Rather, Naoki Urasawa follows a group of children in flashback. We know that one of them is Friend. But we never find out who it actually is until the very last chapter, when Urasawa makes a reveal that is both suitably hinted at but completely surprising at the same time (I admit to being completely wrong in my guess). Friend's mysteriousness has an extra dividend: it makes him all the more inhuman, and thus scarier.
The problem with this (for someone trying to choose good scans) is this means he doesn't get as many good scenes as the other two. And when he does show up, it's usually something so completely story changing that I'd be spoiling far too much to use it. If I had to pick a good Friend moment, I'd take this rather out of context scan from Chapter 43:

Hopefully this conveys the childishness of the character without giving away too much. Note that "kun" is the Japanese honorific for a child.
Beyond having the coolest visual of the three (I like the mix of suit and mask), Friend's motivation is also interesting. While 20th Century Boys is, in a way, a love song to Urasawa's childhood, that type of nostalgia taken too far can be a bad thing. Friend is representative of that, a man willing to become a supervillain just so that the game of bad guys and good guys won't end. But dig a little deeper, and you find a dark void that can't be filled.
Johan is a similar beast to Friend in many ways. They both have mysterious pasts, they're both charismatic individuals who operate using agents, they're both driven by their own lack of humanity, and they're both willing to do pretty much anything to get what they want. While Friend where's a mask to hide his identity, Johan uses his boyish good looks and a tiny perpetual smile to avoid detection.
The difference comes down to the differences in the stories themselves. Monster's main theme is, simply stated, "No person is truly a monster." Johan, therefore, is much more human than Friend is, simply because exploring Johan's essential humanity is necessary to the theme of Monster, while similar questions are thrust aside in the case of Friend to preserve the mystery of 20th Century Boys.
This makes Johan both a better and a worse character than Friend. He's better, because we can explore him deeper and learn more about what drives him. He's worse, though, because he's stated to be something inhuman, but you can never quite feel that about him. He's a scary person, for sure, but he never reaches the heights of almost supernatural terror that Friend inspires.
Still, I have to say I like Johan more than Friend (despite preferring 20th Century Boys to Monster in general), simply because you do get those hints of something else going on inside him. He's a person who is trying to become a monster, and you wonder what drives him to doing that. Check out this scene where he confronts a would-be blackmailer while he's running his game on Schuvald (three and a half scans from Chapter 65):


This is where Johan succeeds where Friend fails. Friend merely scares me. Johan can do that (although not as well), but he also haunts me. Just try to disagree after seeing those eyes. Continuing on with the scene:


As I've mentioned earlier, Johan's nihilism is more powerful for its sincerity. He honestly doesn't care if he lives or dies. Can there be anything worse than being what he is? Johan's lack of concern over his safety is represented by one of my favourite recurring motifs in comics: pointing a finger at his forehead while a gunman threatens him. There are a number of variations on it, but it never quite seems to lose its power. I'd post them here, but this post is already running quite long. I may do another post with all of Johan's "shoot me" moments.
And finally, there is the powerful robot, Pluto. Pluto is different from the first two. While Johan and Friend are defined by their inhumanity, Pluto is a robot with too much humanity. This is an interesting subversion of the standard evil military robot story (including the original Astro Boy story "The Greatest Robot On Earth"). Usually the story goes something like "Robot is a weapon, doesn't want to be a weapon, learns to be more human, dies proving that it's no longer a threat." Pluto twists this around a bit: what happens when you teach a robot to love and then take away the object of its love? To answer that question, let's take a look at what the first appearance of Pluto in the very first chapter looks like, shall we?

"I hated her, so much... it-it- the f - it -flam - flames. Flames, on the side of my face, breathing-breathless- heaving breaths. Heaving breath..."
Joking aside, I'm actually strongly reminded of Munch's The Scream. Ignoring the more obvious similarity in the central figure, the colouration of the flames reminds me of Munch's famous sky and the whole painting style looks similar to me. It's also an interesting comparison in context: while The Scream represents a feeling of terror, "an infinite scream passing through nature", Pluto himself commands the forces of nature and is treated as one. Pluto, despite his own cry, is not the screaming figure from Munch's work, but the infinite rage and power that stalks that hapless person.
Pluto can't handle his humanity. He has the emotional maturity of an adolescent, and he the things he's been through have broken him horribly. His rage consumes him almost utterly, driving his actions beyond reason or pity. Ironically, this makes him strangely more effective than either Johan or Friend. While those two require intricate planning and psychological button pushing to spread their own inhumanity, Pluto merely has to give in to his own hate to breed more, as seen in this fight between Pluto and a revived Atom (three scans from Chapter 61):



And that's the grand link between the three. Johan and Friend's inhumanity, Pluto's hatred, they all attempt to infect those around them, in a misguided attempt to fight the original by becoming greater. Ultimately, the true test of the hero is not fighting the villain on his own terms.