We never let any of our children cry it out. My advice is to get the child into a schedule so that they are very tired come bed time. Meaning they must be up from the nap at least six hours before you want them going to sleep for the night. For some kids it might take 7 hours.
The point is that you get them into a schedule where they are falling asleep in your arms and then you just put them down in their crib.