Seeking musical selections

What songs would you put on a cross-country road trip play list? Making purchases from iTunes soon. Road Tripper #1 likes music she already knows, a.k.a., oldies and/or classic rock. Road Tripper #2 likes the CD101 mix and I’m not sure what else. I like music that keeps me awake and happy on the road. I need a good variety of all of the above.