I've been rewatching Swan Song lately and was reintroduced to this glorious moment of Monster chilling from Geoff (Week 32 part 4). Blur edited in for Week 32 spoilers.
Of course, there are many moments that comes to mind when I think "favorite Rollplay Moments", like Lord Wyman from R&D Dungeon World, the Crazy Saxon from Pendragon, and Jessies crazy turnaround during Numenara. The whole last episode of R&D Saga of the Islanders.
Mr. S pirate ship stunt, the space walk, and Titanfall. Anything Howard. Basically everything that happened during the Asa race arc, and many more.
Tudagub's sacrifice, and trying to open up Big Vinnie's. Vincent's many, not so succesful duels. Bregor's ups and downs. When Geoff played a scottish cleric and cast Obsesive Compulsion on a lord.
Speaking of which, I'd love to see a Highlight reel of some of the best parts of each Rollplay show.