I've read many posts about picking recommenders. I've had people mail me and call me about my tips on picking the recommenders.
My own strategy for my recommendations was simple.
1. Pick those who I know really well, and whom I trust to write positively about me. I chose a former boss and another colleague who had watched my career grow. Both knew me well in professional capacity.
2. They did not have to be the CEO or the VP (I could get my recos from both). I wanted my recos to have substance and bolster my case. Not generic "I know him and he's the greatest since Isaac Einstein*"
You may be surprised, but apart from asking my recommenders to be nice to me, I did not write my recos, I did not see what they wrote, and I did not ask what they wrote. All they did after filling the recommendations online was to say briefly that they wrote good things and I left it at that. And I am absolutely certain they were professional and kind in their words. This sort of comes to a point that it is important to build solid, reliable relationships at the work place. There are times you get to work with great colleagues, competent bosses - and those are times you make sure you work well with them and create a network that lasts.
Getting a recommendation from the current boss can be tricky for obvious reasons, but I suppose it varies from people. I recently approved vacation to a team member so he could study for his exams. My reasoning was simple - he is a great performer and he was honest with me. My expectation was that he be committed to his job as long as he stayed. So now, he is committed and knows I supported him, and I know that I will not be blind sided by his decisions. If you have such an equation with your boss, he may be the right person as well. Of course, you would not gloss aside the fact that I empathised with him as I knew what he was aiming for (and so am I).
Given favorable circumstances, I think it is good to choose recommenders whom you trust and who know you well in a professional capacity. The titles and designations come later - I don't think adcoms of top business schools would be impressed by high sounding titles. Just as a personal perspective, I have interviewed candidates who got their recommendation letters from ministers. If nothing else, it cast a doubt on their candidature than strengthen it and it did absolutely no good to them. You want your recommenders to paint a compelling picture of you, not some hotchpotch modern art. With due respect to modern art ;)
*yes, I really meant Isaac Einstein.