YES music does help a lot. Research has shown that classical music does help to calm shelter dogs. Attention is always helpful too. Maybe you could play with him inside, just before bedtime? Especially on the weekend.
I am so lucky. Since my dogs were raised in their pens and have everything they need they don't wake me up. I need to get up to feed them, but they still don't bark to wake me. The little one 'groans' and wakes me up!! Today after a bad night, I didn't wake up until 9:20 am!!