Has anyone recently removed headrests from '69 B-body bench?
The drivers side came out with a little bump, after it was fully
extended. The pass. not so easy. Is there a trick, I don't want
to break anything?

The headrest tend to stick and you won't break anything by pulling on them hard. The only problem I had once was smashing my hand on the roof and putting a dent in it under the headliner... Sometimes it helps to tilt it forward or rearward when pulling.

I had one that was stuck in my Duster, and when I wrestled it loose, it continued upwards and ripped the head liner when it struck with force. Be careful, probably better to tip the seat forward and work.