Madonna, 'True Blue'
It's been a long time since Madonna has released an album that connected with a mass audience, and her live show tends to be divided evenly between huge hits and brand new tunes much of the arena doesn't know. Why not break out of that cycle by re-staging a classic album like True Blue? Songs like "Live to Tell," "Papa Don't Preach" and "Open Your Heart" have aged remarkably well. It would be a huge event that would really fire up the Madonna faithful. From there, she could do Ray of Light and Like a Prayer. It would be the perfect way to give her career a huge jolt.