Just an idle thought - there are SO many politicians, celebrities, etc., you definitely would NOT like to spend an evening with in a pub - the other day listening to some R4 programme on the life of Churchill, we looked at each other and said "him, we'd like to meet him in a pub!"
We both abhor his politics (as he would ours), and all the rest of it (leaving aside winning WW2 against the Nazis of course), but we think he'd be a really entertaining companion over a few pints. Funny, a good listener, full of stories (what a life!), and in some ways sympathetic and thoughtful.
And there ain't many you can say that about these days...
the labour candidate elected to parliament in this locale in 1997 continued to visit the pub that had previously been his local, and continued to be a regular after losing the seat in 2010. at all times he needed a thick skin as the local gimmers called "order! order!" as he entered. but he always took it with good grace, and was always an interesting sharer of a pint of marston's pedigree...
Nigel Farage, David Niven and Peter Ustinov would be my choice. I am sure Sir Winston Spencer Churchill would be over subscribed so I would be happy with my other three choices.