Oh man.  So this happened last season.  Fresh off of getting expansion GM for GFG, I teamed up with @steveoiscool to execute a beautifully executed gator on @ACapitalChicago, much to his dismay (but also took it in most admirable stride).  It was, as far as I've seen, one of the best gag's pulled off.

Other than that, I would have to say (not anything I've done), seeing @brickwall35's flawless execution of a gag on @Kalakar is arguably legendary.