I shaved my head in May of 2000. I was tired of trying to make my hair do what I wanted while my hairline climbed steadily up and over.
Best move EVER! This was a year or so before it was trendy. I had quite a few women tell me they thought it was sexy as hell. Not only did (do) women find it sexy, it is the easiest hair style in the world. Every few days I shave my head. Other than that, no combing, shampooing, or worrying. I can wear a hat for half a day and not have "hat hair". I can go from sound asleep to dressed for work in 5 minutes flat. And I can drop the top or roll down all the windows on my way to someplace important and still look good.