Hmmm....he's going through a lot at this stage. Does he have his 2 year molars yet? My son teethed without a problem until he got his 2 year molars and that was a rough time with lots of night waking.
Definitely do not turn on the TV! That is just not conducive to relaxing at all. If he is taking milk then he might be hungry? Maybe a last minute high protein snack before bedtime would help? A bit of peanut butter on crackers? Yogurt? String cheese?
It is a phase and one that will pass! I never understand moms who respond who will tell you that he should be trained to sleep....people (kids and adults alike) wake all of the time. We have the ability to go pee, get a drink, a snack if we are really hungry, or just lie quietly and think about our day, our stressors, etc....He doesn't have that ability and relies on you to help.