I have a number of staff in my team, and I'll take the occasional friendly dig like anyone else, but you might want to remember a few tips (which apply to everyone really).
1. Check the mood of your boss first, he has demands you probably know nothing about, so be aware.
2. Be careful when playing to an audience, if the boss thinks you are undermining his position (especially in front of his boss), you'll be shut down real quick.
3. There's a fine line between negging and workplace bullying, and that line can change depending on point 1. You could be taking your first step into dismissal territory.