Speaking of Speak Now's poor transitions, I made an alternate playlist a while back that I don't think I ever posted here...
1. Enchanted
2. Speak Now
3. Back To December
4. Mean
5. Never Grow Up
6. Sparks Fly
7. Dear John
8. Ours
9. Mine
10. The Story of Us
11. Haunted
12. Last Kiss
13. If This Was A Movie
14. Long Live
15. Better Than Revenge
16. Innocent
17. Superman
I think this transitions better because it's country pop -> country -> country pop -> pop. Innocent as a bonus track because it completely kills the momentum of the album, BTR as a bonus track because it's just so pop. I also separated BTD and DJ with 3 uptempo songs so that the 2 long ballads don't weigh down the album's first half so much.
This also works because:
Mean's "someday I'll be livin in a big ole city" is followed by Never Grow Up's "... in the big city... it's so much colder..." and Sparks Fly's "you captivate me baby just like a fireworks show" is followed by Dear John's "shining like fireworks..."
