One of the best successes I had when I participated in organizing the occasional office party was hiring a comedian. I guess many people think “stand up” when I say comedian, but this isn’t so.
Whip open your Yellow Pages or Google Local Business. Find a comedian who does parties. Call a few. I found that comedians were more expensive than having a magician (magicians are great for kids parties) but it was well worth it. Call a few more and get quotes for a party. Interview at least three comedians and determine the best one for your group.
We found a comedian who, during the interview, brought us to tears without even cracking a joke. The idea is that the office party was to be held at a local restaurant reception hall with waited staff. The comedian was to blend in as a server and just be totally moronic about it, get the patrons (yes, this could be your boss) orders wrong, and short of starting a fight, had a victim for every joke he pulled, but in good taste.
When we signed him on, we provided a list of employees’ names, their latest photo, and their biggest gripe or running gag. The comedian fully exploited these “little character flaws” and it took about an hour before everybody realized he wasn’t really a server. It was classic. At that point, everybody wanted to be served by him and be the butt of his jokes. Then he opened the full canons and organized the sixty of us into about us into groups of about six and just had us do the most embarrassing dares and challenges for another couple of hours, all the while making it “good taste” funny and hilarious. We talked about it for weeks after.
Expect to pay about $400-$800 for a good comedian for about 3-4 hours of entertainment.