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Were tip jars common in NYC before Starbucks popularized them? I don't remember them at all but maybe it depended on the type of place?

I would say they were common enough per my memory of 2000s, certainly not ubiquitous like the POS tipping options today.

It was common enough to be part of Seinfeld, at 1m10s:

However, I do not feel like there was any cultural expectation of tips for counter service. Or I did not notice because I never used cash anyway.

Oh that's a great catch, and that episode was 1996, so wouldn't have been a response to Starbucks.

Now it's really got me wondering how far back those plastic tip buckets at mom and pop shops like pizzerias and deli counters go.

No. People would have stolen them.