I’m pretty semantically flexible with the word “street,” since it is such a grossly ambiguous categorization anyway. And after all, the OP’s point was how to get a portrait shot of someone on “the street,” fair enough.
However, to say that candid street shots (and I qualify such as ‘candid’ since street doesn’t even have to contain a human subject) are somehow “archaic” or exists to feed one’s ego is ridiculously simplistic and completely untenable.
For one thing, photographing a fleeting event is not an aspect saddled with a historical expiration date, lest photography itself become a dreadfully prosaic art. And yes, an extremely relevant aspect of candid street shots involves the transient aesthetic, one that often cannot be recreated nor necessarily should be recreated.
Secondly, instead of citing the currently most famous street photographer (whoever this might be in your mind), you might want to look around at the actual state of street photography because it is quite broad and diverse in its overarching style. For it to funnel into one particular trend would be most unfortunate.
Thirdly, you might want to clarify on how you are applying “stupid” and “weird.” Are you merely targeting people who essentially brag that this or that shot was “candid,” as though the photograph was great largely for this sake alone (which was not Reservoir Dog’s point)?
Or is your chastisement directed at all of candid street photography, in which case you would basically be denigrating not only many of the world’s greatest photographers (irrespective of genre), but their numerous admirers.
Concern for privacy and respect is understandable, and the extent to which a photographer imposes on another person is undoubtedly a matter of reasonable debate (this goes for legitimate reportage too, not just candid street).
But as I’ve said on this site in the past, I would hate to think that the photographic scope of humankind should be reduced to posed shots or those only taken with precursory consent. “Street portraits” have there place, as do documentaries where the subject and photographer have an established agreement. But equally valid is the photographing of life unencumbered by preemptive direction.
And should Henri Cartier-Bresson be out of style, so should Shakespeare, Mozart, Davis, Joyce, Rembrandt, Adams, and, well, the point being is that great art, however weighted it might be by the label subjective, is nevertheless timeless. And really, taking portraits of people, whether on the street or in the studio, is not exactly a new concept. In fact, it predates the days of HCB…
And please, let’s not presuppose what Cartier-Bresson would be doing today, any more than we should question what Van Goh might be doing today, since such speculation is just that, speculation. Moreover, it’s largely irrelevant, since what they actually did is what matters.
Besides, any ‘change’ to conform to today’s expectations doesn’t mean that such change would be for the better…and I certainly haven’t seen anything that would suggest such improvement inevitable, far from it.
But yeah, I’m out as well, since consensus on this issue will remain elusive, and more importantly, it digresses from the OP.
By the way, if time permits, suggestions to take individual shots of all the group is a good idea; and who knows, the best photo might actually be of someone other than the intended subject.