I'm going to address the second question first. I have a couple of songs that will pump up my energy based on my mood. The "Power Song" I have set on my MotoActv is "Stronger" by Kelly Clarkson. I downloaded it a few months ago when I was having a rough time and needed something to boost my mood. I really like "Freebird" by Lynyrd Skynyrd for the end of a run. I also find that "I'm Shipping Up to Boston" by the Dropkick Murphys (from The Departed soundtrack) and "I Know You Want Me (Calle Ocho)" by Pitbull put my pace solidly around 9:15min/mi (I run between 10 and 11 normally).
Okay... Playlists.... I have several based on my mood and length of my run. I have some that shuffle and some that don't. I have one that is just called "Running" and has 65 songs on it and randomly shuffles. I have one called "45 Minute Classic Rock" and it is about an hour of music from 20 or more years ago. It kills me that "Mysterious Ways" by U2 is played on our local classic rock station, but it does fit in more there than in my "60 Minute Pop" playlist. That one is full of Katy Perry, Pitbull, and similar stuff. It also is the home to the songs I like from Zumba. Then I have one for a 120-minute run that is a mix of everything.
I haven't decided to what I am going to listen for my Ragnar runs. My guess is I will go with a straight shuffle for my 7.9-mile leg and 5-mile leg and do the pop playlist for my 2.2-mile leg. I top-loaded that one with my speed-inducing songs ;)
What's on your playlist?