Slight variation on the original question but I can't believe how old people used to look! I have one of those long school photos taken in about 1965 and even though I know that some of the teachers were in their mid twenties they all look to be 40+! The pupils look much older than their ages too, maybe it's being in black and white.
I quite like the one of Blair in Ladybirder’s link.
It looks like he’s contemplating that he shouldn’t have been Bush’s puppet, taken us into an illegal war and caused the death of hundreds of British servicemen.
It always makes me wryly smile how some people lionise Blair and yet conveniently forget (and they do conveniently forget) that he directly and unnecessarily caused the death of so many people.
In trying to give Mrs May a level of political and personal gravitas, when in reality she has the absence of either, gives her a sense of sterness and power that again, she simply did not, and does not possess.
It's an attempt to graft onto an image of Mrs May the desirable political advantages of a powerful and authoritative nature, neither of which she had then, or has now, which is why she was a poor leader and an ineffective Prime Minister.
I think the artist has pretentions to aspire to the late genius Salvador Dali, who always hoped thar, rather his portraits captured the essence of his subject, that the subject would come to assume the essence of Dali's portrait.
This artist is several galaxies away from achieving that aspiration.