That guy sounds like he's having a good time...but when it's time for the facility to do their quarterly tape reviews, he'll probably fail in the first 30 seconds....
I like to make small talk with the pilots here and there...and I try to be as helpful and cordial as possible...controllers just have to remember, everything is being recorded...if there is an accident...even though not your fault, investigators look at everything, lawyers look at everything....the reason we have FAA evaluation teams touring the country all the time is to help us neaten up everything that we do...not to punish us...to help us because of frivolous lawsuits by victims of accidents and such.
Again, I like humor and love to lighten up the mood on the frequency, but we always have to be careful...and fortunately for me, it's never came back to bite me!