Michael Bluth and Jeff Winger are not that different. Both are highly motivated extroverts with a strong dose of charisma (at least within the context of the shows they’re in) who tend to become the centre of their world by dint of being the strongest driving force within it, someone whom other characters fight either with or against. Both are also defined by a strong sense of ambition and vision that drives them both within individual episodes and on a broader series-wide scale, and for both men it’s something that makes them smarter and more sympathetic than the average sitcom protagonists of their day, as well as making their successes, failures, and personality flaws grander and more interesting. What separates them from each other is that they’re playing with very different sets of data.
Jeff is sometimes diagnosed as being a sociopath, but that’s never really worked for me. The single most defining aspect of his character to me is his empathy. Jeff has an acute awareness of the feelings of others, and his ability to play to that is the source of much of his success in his life and much of his charm as a character; his ability to instantly recognise and seize an opening is part of what makes your average Community episode so thrilling to watch. The flipside of this is laziness. At the beginning of the series, he’s so used to relying on charm to get what he wants that he’s crashed and burned out of being a lawyer because he tried taking the easy way out, and so many episodes of his show are about him trying to find the path of least resistance and finding what appeared to be the long way around was actually the faster way.
Laziness is not Michael’s problem, unless you count the laziness of his family piling more problems onto him. Michael’s charm as a character comes from his effortless wit and relentless competence; on a broader level, his stories are often about trying to untangle his family member’s various lies and trying to keep the business on track, and on a moment-to-moment level his wit cuts through their bullshit. What often trips him up is that same competence and wit; his particular brand of Bluth lying comes out when he sees the fastest way to get what he wants and impulsively acts on it, often sacrificing a long-term value for some short-term gain (more often than not, sleeping with a beautiful woman); his interest as a character comes from his inability to juggle his various motivations.
Another way of putting it is by looking at the character’s mirrored sense of self-image. Jeff’s people-oriented worldview means his sense of self is driven by what the people around him think; Abed accurately notes that he has one of the most fragile egos in the study group, which is the other flipside to being incredibly emotionally sensitive, and his stories are often about him trying to push one image on other people before being forced to reconcile with what he actually is and wants to be. Michael’s ego is much more personal; he’s created a distinct image in his mind he wants to live up to, and it’s rare if he gives a crap what anyone thinks of it; Jeff feels public shame very intently, but Michael only feels shame if he, personally, feels that he’s crossed a line. The difference between them is present in their speeches: Jeff’s famous Winger Speeches are loud, directed at his entire community, and are intended to be shared with that entire community – ‘We can all be this person together’. Michael’s speeches, when they aren’t based around shaming everyone else, are often directed at one person, and even more often are intended for his own benefit than anyone else’s – ‘I can be this person’.
They reckon if you swap the protagonists of Hamlet and Othello, both plays are over in ten minutes. Swapping Michael and Jeff around doesn’t undo either show, but it does drastically change things up (especially if you stick to both shows pre-reboot first three seasons). Part of Jeff’s growth throughout Community is tied into Jeff’s newfound, uh, community slowly warping him into a better person; I can see the world of AD degrading him very quickly as he picks up awful habits from the Bluths and realises just how much he can get away with. Conversely, Community‘s unforgiving goodness would unravel and possibly rebuild Michael so much faster. Ironically, I suspect the fragility of Jeff’s ego makes it easier for him to bounce back from his failures – it feels to me like Michael could be completely broken by that world.