One issue is that many modern definitions on cynicism actually define it deep on the negative end of the scale.
For example, an Internet summary from Oxford Languages lists:
Cynicism:
1. an inclination to believe that people are motivated purely by self-interest; scepticism.
2. an inclination to question whether something will happen or whether it is worthwhile; pessimism.
3. a school of ancient Greek philosophers, the Cynics.
Note that point 1 comes off quite extreme at first – it can be read as if to be cynical would mean to believe that people are motivated purely by self-interest! As if being cynical is all about that, and leaves no room for other ideas. But it also paraphrases that as “scepticism” (also another ancient Greek philosophy which doesn’t exactly map to conventional definitions), but note that IS NOT what scepticism means.
Oxford Languages lists:
Scepticism:
1. a sceptical attitude; doubt as to the truth of something.
2. the theory that certain knowledge is impossible.
And similarly, definition 2 of Cynicism above says “pessimism”, or more generously, an inclination to question things!
An inclination to question things, I would say, is an example of healthy cynicism, even with some cynical humor thrown in.
Other examples would be any case where a nasty person or group is putting forward disinformation, such as in politics or advertising or propaganda, and that false message can be justly and effectively (and often, entertainingly) destroyed by an accurate cynical parody.
Like practically all of The Colbert Report or other comedic satirical news shows, which have tended to mostly be more accurate and honest journalism than most mainstream corporate news for at least two decades now, e.g. Jon Stewart, John Oliver, Trevor Noah . . .
I consider pretty much all the Pitch Meeting videos, and much of Ryan George’s other videos to feature a lot of positive cynicism, too. Note that it EXPOSES the terrible patterns of some others (including but definitely not limited to selfishness) WITHOUT holding a position that EVERYONE is like that. In fact, Ryan George is a great example of also exemplifying contrasting healthy/reasonable perspectives at the same time, which I think is part of what makes his videos so often hilariously ring true.
Or this recent review by The Critical Drinker (typically good for some humorous but usually positive cynicism) about The Truth About ’‘Toxic Fandoms’’ . I think The Critical Drinker is an important example of how cynicism can effectively and appropriately reveal gaslighting, by refusing to give more politeness to gaslighters than they deserve.
And I’d say the common arguments against cynicism tend to place too much faith in the idea that in actual society (not to mention media or politics) the mainstream message doesn’t deserve any skepticism or resistance.
There are many other possible flavors of healthy cynicism as well, but there are some examples.