Something that I've avoided during most of my time playing music is singing. The reasons why? I can't really sing in a voice that 1) is tuneful to my ear and 2) doesn't rip up my throat. I've never taken singing lessons and am frankly utterly embarrassed by my attempts to properly sing lead. That's probably why I like doing songs in karaoke where I don't have to properly sing. Doing "Copacabana," "Scenes from an Italian Restaurant," and "It's the End of the World As We Know It (And I Feel Fine)" don't necessarily require pipes; you just have to talk really fast.
Well, something has recently developed where I actually sing harmonies, and I don't feel weird about it.
Playing music with my friend Nick is always something I've enjoyed. We played together in the 11:30s and have jammed for fun many times since then. There's a great degree of comfortability in playing with him, and I don't feel self-conscious about trying different things out. One of those things is backing him up vocally on a number of songs he's been cooking up for the last few years. Since I'm familiar with most of these songs, I figured during one late-night jam to just sing along. Doing that didn't feel weird, so I've kept doing it since then.
I've seen plenty of examples as to why a drummer should not sing. Trying to hold a note in tune is hard when you're craning your neck as you're using your entire body to keep the beat. One very memorable moment I saw firsthand involved a Fort Worth-based band that one of my bands opened for. The drummer had no vocals in his monitor, had his vocal mike pretty high in the mix, and his voice was nowhere close to being in the right key during the entire set. I think I swore off drummer vocal mikes after that, but I've come around.
So, this leads me to where I am now; fine with singing in the background, but really have no interest in singing up in front.