Michael Scott. He may be a Too Dumb to LiveJerkass, but then you consider his horrible relationship with the bitchy Jan and his depression after his roast and his short-lived romance with Holly, whom he still holds a torch for. Also, in general his lack of social skills can be a downer sometimes.
Even further than that, throughout the show, it's clear that most of Michael's decisions (becoming a salesman being a big one) are made with the intent of either making friends or finding romance. Unfortunately, failure seems to be the only option for him, as bad luck tends to break up any chance at either that Michael's own thoughtlessness, childishness, oblivity, or generally self-centered nature doesn't drive away first. It gets really woobieish at the brief points where Michael actually realizes this, such as in "Bring Your Daughter to Work Day" and "Koi Pond".
The "Fundle Bundle" tape with young Michael qualifies as Mood Whiplash.
Also, some episodes point out that he really wants children. The "Fundle Bundle" above is an example (though he wants them for selfish means, as he says he wants friends who won't have a choice in the matter), as is "Bring Your Daughter to Work Day". One of the arguments he has with Jan is that he wants children (he bought a whole condo for them!) but she can't decide if she wants kids with him (she forces poor Michael to have a vasectomy, then reverse it and then have a SECOND vasectomy whilst making that particular life decision!). Even in "Chair Model", when he tells everyone to find a girl to set him up with, he flat-out states that he wants to play with his children before he gets too old. Even Creed tears up.
Dwight can be this in some episodes.
Pam's become one in later seasons. Interesting in that she started off as The Woobie, and developed Jerkass tendencies. Examples include: mocking how the senator proposed to Angela; manipulating Dwight, claiming they've been great friends when she knows that's not true, so that he can take care of her daughter for a night, so she (Pam) could sleep; lying and manipulating her way into a nonexistent job where she created her own higher salary because she couldn't cut it as a salesman.
Nellie is a bitch who stole Andy's job and not only got away with it but basically kicked off a downward spiral that got him fired. On the other hand, we learn that she does have feelings that can be hurt and that her life is crappier than Michael Scott's was: Due to her shopping addiction she's maxed out all of her credit cards and is in serious debt, she's been rejected for adoption because she's unmarried, she doesn't have any friends or a social life and her family lives in the UK. At the top of the ninth season Andy becomes blatantly abusive towards her and announces his intention to fabricate a reason to fire her, again making her more sympathetic by comparison.
Angela is rarely sympathetic, but it's hard not to feel bad for her when she's inconsolable after her cat Sprinkles died. She's very attached to her cats, and anyone who has lost a beloved pet knows how upsetting it can be.
As this video point out, Jan can qualify, considering the toxic workplace environment she's having to put up with and her relationship with the childish and idiotic Michael wearing down on her sanity.
Roy. Even though he was definitely an inconsiderate oaf of a guy with Jerk Jock tendencies, he was never actually particularly mean or cruel to Pam- their arguments were more rooted in their incompatibility than anything. Plus, despite his idiotic comments about other women’s looks in front of Pam, there was also nothing to suggest he ever actually cheated on her. So, this makes it easy to forget that she was spending years flirting with and ultimately kissed a guy behind his back at the end of the day- which especially sucks for Roy since he trusted Jim enough to leave him alone with her that particular night in the first place. So, even though they clearly weren’t right for each other and Roy’s no blameless victim in his engagement falling apart, anybody who’s dealt with a partner and a “overly-familiar” coworker can probably sympathize at least a little with his shock and heartbreak at losing Pam to Jim.
point out, Jan can qualify, considering the toxic workplace environment she's having to put up with and her relationship with the childish and idiotic Michael wearing down on her sanity.