I enjoyed the Sir Scott calls mostly due to Tom potentially laying the bait for the kid to break character a la "You thought I was your friend, but I'm your FOE!" I mean, we'll never know what would have happened if the kid had gone for it, nor did he, but a moment of understanding and a moment of roping the kid in and then torpedoing him were equal possibilities and I love the tension that exists there.
This should probably go in the underrated Best Show strengths topic, but one of those things that Tom can do on a live radio show with callers that podcasts don't do - and one of those things that makes listening live such an experience - is the moment when Tom reels in a caller on something and they may not know it's happening. He just sets those traps (for lack of a better word), be it luring someone into dropping a lame comedy bit, tricking someone into getting themselves Heave Ho'ed or just catching someone off guard by either making up a fake fact or claiming to be ignorant of something he most definitely knows, and you get those seconds where you can sense the caller trying to decide whether to go for it or not.
I can't think of anybody who pulls that kind of thing off more consistently and makes it as funny as Tom does.