1. To choose something very carefully to ensure that the best option is chosen, perhaps through means that provide one an unfair advantage or from a selection that others do not have ready access to. I can't believe he left the company and then cherry-picked the best employee in my department! Yes, you will get to cherry-pick all the equipment that goes into your studio.

2. slang In sports such as basketball and soccer (football), to position oneself away from the current play on one's opponent's defensive end for an opportunity to receive the ball and score an easy basket or goal. We might not have gotten scored on if you had actually been playing defense instead of cherry-picking!