i thought it was cleverly done
the issue with the "awkwardness" is just john oliver's interview style...he's also done interviews with that jane ape woman and stephen wheelchair man, i think it's a borrowed style of cringe humour from ricky gervais' the original office
regardless of whether you like this style or not, john oliver's bringing big important topics that americans ignore due to them being boring and feeds it to them so that they're actually able to swallow it instead of throwing it back up if it were delivered in a serious manner
just think of all the interviews that snowden has done already....most ppl in america didnt care, most ppl in america forgot about him
now when, oliver brought out that laptop showing snowden that no one remembers him, that was extremely harsh, but even i think snowden realizes that oliver is doing him a favor
snowden was under the impression that because this was such a violation of privacy that ppl in america would naturally care
his problem is not knowing his audience, americans were too uninterested to care
by oliver showing him the problem, he then offered a solution on his show with that dic pic thing
oliver was on snowden's side the entire time and im sure off camera he explains the nature of the interview so snowden was prepared for it