Need help- sleep

Ok so my guy started sleeping through the night very early on until about 6 months. Then nightmare for about 2 months. And then doing ok with just waking up once. However he still is unable to soothe himself to sleep. He does it sometimes if he wakes up in the middle of the night or from a nap too early but he absolutely refuses to do it to go down initially.

We have tried cry it out it doesn’t work. This kid is so stubborn he will literally either 1) cry forever (over an hour) until he’s so tired he’s falling asleep sitting up but refuses to lay down to sleep and will just keep doing this and crying. Or 2) will cry for a while play for a while cry repeat repeat with the same outcome.

Any tips. ?