I guess it's probably different for diner servers or something tho. Some people have worked long enough in the biz to make 50-100k a year and are no longer willing to take that for a pack of smokes and a 40. The finer the restaurant the less likely the server is to tolerate that I figure.

I'm thinking like, if i worked at a place with $8 entrees and $3 beers, where your tab would be around $60 and that $20 is actually a 33% tip, I'd probably be more likely to play along with someone trying to show off if it results in a good gratuity for me.

Here a $20 tip for a party of 4 would be realistically 8-12% max, so I'd basically lightly tell the person to go fluff themself. Not worth the egotistical BS.