Generally I've found wire beaded tyres to be more of a pain to fit than kevlar beaded folding tyres.
I wish I remembered some of the combinations that have proved the most difficult to deal with. There was a combination a few FNRttCs ago, that we had to fit multiple times, and took three of us, using a VAR lever and two tyre levers to get on. Inevitably on at least one occasion we ended up putting a snake bite into the inner tube when putting it back on. I got better at removing it (I think we had to do that five times before we gave up), but we never really sorted out how to get it on efficiently, we just barely managed. I've very rarely had problems fitting tyres on, I think this was only the second occasion on a FNRttC when I've had significant problems, so I'm reasonably practised at removing and replacing tyres. After an hour or so, we gave in, and left the guy with the bike waiting for a Taxi that he'd arranged to come and pick him up.
I forget exactly who I was with, but Adrian did join us after the first couple of repairs, and whilst that gave someone else to help turn the air blue, he didn't have any more success than the two of us TECing at that point had previously had.
It was a narrow Conti racing tyre, but I don't know what the rim was, or the exact Conti tyre.