#and specifically as having more influence with henry than anyone-- save anne. who's judged as having the most.

[fideidefenswhore]

Something I have been meaning to ask in hindsight who do you think Henry's "best friend" was? I know this is a fairly modern concept and King's would of thought he was only equal to other Kings. But, something about Brandon being given this honour when we also have Compton does not sit quite right.

Glenn Richardson had an interesting insight into this question (that I haven't seen replicated or cited much, really):

The letter’s many pointed references to Wolsey as the king’s friend were intended primarily to remind its recipient of his duty. Yet, although full of angry sarcasm in the moment, Henry deployed them sincerely, and the letter may plausibly be read as evidence that he really did genuinely think of Wolsey as his friend, as well as his servant, and in a way very different from almost anyone else. Diplomacy with Francis I aside, the only other person whom Henry is recorded as calling his friend, on paper at least, was Anne Boleyn.

But assuming you mean male friends, I would say different eras mark different men having the most confidence with Henry. Of friends that were his 'earliest' companions, and were covert or overt supporters of CoA and Princess Mary; there were few survivors (Edward Neville, Henry Courtenay, Henry Pole, etc); and some that survived but lost favour, whether temporarily or otherwise (William Fitzwilliam, Geoffrey Pole, etc). And of friends that were strong supporters of Anne Boleyn, either by kinship or friendship, there were also few survivors (George Boleyn, Henry Norris, and Francis Weston all seem to have enjoyed close friendships with Henry, the former two the strongest, arguably), and likewise (Cranmer, Richard Page, etc).

We can view Suffolk as having survived the political culls by expressing loyalty towards Henry above all others; Compton he was probably closer to as you said, and then Norris inherited that confidence. Heneage he doesn't seem to have been as affectionate towards.

Among friends/advisors, those that Henry seemed to have the most fervent concern for during their illnesses were Wolsey, Anne Boleyn, and Cromwell.

If we're including friends of spiritual authority, I would say Wolsey and Cranmer, if we're limiting to secular power, I would say Compton, Brandon, Norris, and Denny were his closest friends.