Hi R., my 19 mo. old has been doing the same thing -- crying L-O-U-D. I think it started when he had teeth coming in and would wake up in pain and got used to us coming in to soothe him. Check his gums, see if he is currently teething. If so, Children's Motrin last for 8 hours (longer than Tylenol) try that before bed.
If he's done teething, then he got used to the "new" routine of being soothed when he wakes. Everyone wakes up 3-4 times a night and we re-position ourselves and go back to sleep. He's waking up, not happy that he's awake, despairing, and wanting to be soothed. Perfectly normal! But not so pleasant for Mom and Dad.
I do not advocate the "cry it out" method. You can read the following article from Harvard University re: why. . . http://www.hno.harvard.edu/gazette/1998/04.09/ChildrenNee...
What we've been doing: we go in the first time he wakes. No talking/reading/singing, only gentle soothing "Shhhhh" and lay him down with his blanket and paci, then rub his back. If he pops back up to be held, we hold him for a short while. . .5 minutes tops. Then, lay him down (as before) again. Then leave, even if he cries. If he continues to cry, wait 5-7 minutes, go back and try again. Continue until he goes to sleep, lengthing the "cry" time by a few minutes each time.
We do the same if he wakes a second time. However, if he wakes a third time or more, we don't hold him anymore. He just gets the gentle "shhh" and so on. It seems to be working and he is crying for us less.
This method is soothing and reassuring, yet clearly tells him "it's bed time and I mean business".
Good Luck and God Bless!