When do they stop crying πŸ˜‚

My son was rocked to sleep up until this month. I figured enough is enough. I rocked him to sleep because he would scream and cry so much any other way. He's 14 months now and I gave in and I have been putting him down awake but drowsy, as recommended by our dr. He absolutely SCREAMS like bloody murder. He now only screams for about half a minute(at first it was 15 minutes then less each night) then falls asleep but it breaks my heart. And I wait until he's very tired...But he hates being put down like this. I know I shouldn't have waited so long but I never agreed with cry it out and now I felt like he was stuck not knowing how to fall asleep. He cries for a short time but it's so loud and sad. How long **typically**until they stop crying when you put them down? Any other tips for me? He's sleeping so much better now! I just wish he wouldn't scream such a sad scream when I place him in bed πŸ™ I've always tried to do anything he needs but the Dr feels I spoiled him