If you sit at the bar or go to the bar for your drinks you should tip the barman each time. I worked in a bar in Manhattan and the barmen always hated tourists who wouldn't tip per drink but only at the end, sometimes they would even point that to the person! The barman will be more inclined to buy you a drink back if you tip this way.
Working as a waitress my weekly wage was ridiculously small, if I remember correctly it was $120 but I made alot in tips! Same goes for chambermaids etc.
You don't always have to tip in cash either, I was often tipped by credit card, the person would add my tip on to the credit card and then the barman would put it through at the end of the night! Sounds dodge but was commonplace.
Most people also tip taxi drivers.