Not just humor, but the overall tone of your application essay is remarkably important. It's also difficult to get right. When you are asked to write about your accomplishments, those 750 words on how great you are can make you sound like a braggart. Be careful to balance your pride in your achievements with humility and generosity towards others. You also want to avoid sounding like a whiner -- use your essay to show off your skills, not to explain the injustices that lead to your low math score or failure to graduate #1 in your class.
Use your best judgment on who you decide to ask - there is no set formula for who should be your recommenders. We know it is not always possible to have a direct supervisor write your recommendation – we would not want you to jeopardize your current position for the application process. Look at the questions we are asking recommenders to complete. Find people who know you well enough to answer them. This can be a former supervisor, a colleague, someone you collaborate on an activity outside of work. How well a person knows you should take priority over level of seniority or HBS alumni status.