Music for a 1/2?

I'm trying to decide what to put in my ipod for the race.
As it is, I generally listen to one 45 min pod cast, and then put my "race music" on shuffle for the second part of the run. Keeps me interested.

However, I run faster and more steadily when i listen to music as opposed to listening to podcasts. If  I go with music the whole way, do I take the time to make a playlist (and download more music for the race) and try to time my songs with where I'll be (and what motivation I'll need) in my run? Or do I just throw a bunch of stuff in a play list and happily let it shuffle away?

Here's who I know will be with me:

Lady Gaga - Bad Romance, Beautify Dirty Rich, Boys Boys Boys, The Fame (Album Mixtape), Just Dance extended remix, shake Ure Kitty, Summerboy, Teeth, Vanity, Sheisse, Money Honey, Highway Unicorn, Hair, Bad Kids, Americano. And I think I need to set Edge of Glory to start playing when i hit my last mile...

P!nk - Raise your gllass, U and UR Hand, CenterfoldI need to add more P!nk

Matthew Sweet- Ultrasuede

Rhianna - Only Girl, S&M, Breakin' Dishes, Disturbia, Do't Stop the Music, Shut up & Drive, Umbrella, boom boom, and my fav: Pon de Replay

Robyn- TBD. I started running w/ her a few months ago but now find myself skipping her tracks when they come up. Same with Katy Perry.

Ke$ha - Yes I'm ashamed, but damn if she isn't katchy

Black Eyed Peas - Party all th eTime, One Tribe, boom Boom Pow, Now Generation, Simple Little Melody, Rockin to Beat, in fact most the album off The End. Silly, yes. Easy to run to, hell yes.

Edna's Goldfish and some Reel Big Fish - cause SKA makes me happy

Ozomotli - Ya Se Fue has got me through more runs than I can count, Lo Que Dice, Mi Alma, Coming War, Cumbia, Donde Se fueron, Oh Le E, Party People, Mi Gente. They'll totally on the list

Jurassic 5 - (can you tell I went to college in LA in the late 90s?) Still have to make my choices off these guys. Too many good songs.

Same for Flogging Molly  - but I Rebels of the Sacred Heart, Tobacco, Drunken Lullabies, Seven Deadly Sins will all be along for the ride

Janelle Monae - If you don't know her, you must watch the videos for Tightrope and Cold War. She'll be in my ears.

I'll have some Beyonce (Single Ladies - I have issues wit hthe song but it's great for running), and I think I'm actually going ot download Britney Spears "Til the World Ends" 'cause damn if it isn't catchy.

Any other suggestions? Clearly I like Female popular dance oriented music, ska, and 90s underground hiphop with a good dance beat.