Sounds like Chris in Family Guy "They have this game there where you in a dollar and you win four quarters! I win every time!"
I would harass people who were fans of certain sports teams to keep from going insane at the restaurant I worked at - I would tell anyone coming through the door (or when they came up to the register if I was cashiering) who was wearing a Pittsburgh Steeler or Dallas Cowboys shirt or jersey (biggest rivals of the Cincinnati Bengals and New York Giants, respectively) that they would be assessed a penalty on their check for wearing such God-awful stuff. I also told people wearing Boston Red Sox stuff the same thing, while I told people wearing Yankees, New York Giants, or Cincinnati Bengals stuff that they would receive 50% off. I always got a laugh out of it and the best was when customers of people who I would "charge extra" would say "the penalty's still worth it" - usually from Boston Red Sox fans.
I still find myself having to do such things to keep from going insane even
Last semester my job for ROTC job really sucked. I was "safety staff" which mant lots of standing around and watching for an hour or two at a time. It was boring and I hated it so we created ways to have fun when times . One day before physical training started we were having a "Family Guy" moment while doing radio checks - we were mimicking the "You must say over at the end of every sentence, over"...."Wait, I have to say over even if the sentence ends in over"....."What, I didn't hear what you said, over".....
Witty responses for when you answer the phone can be fun too. "Hello" or "What's up?" gets old quick.
Quoting Umfolozi (Thread starter): 17. When Leaving The Zoo, Start Running Towards The car park, Yelling
'Run For Your Lives, They're Loose!!'
Humming the Jaws theme at the ocean is pretty fun.
Sitting next to nervous fliers and pointing out at the wing flexing up and down in turbulence and saying things like "you know I could be wrong but I don't think the wing's supposed to be bouncing up and down like that" is fun too.