Yes it sounds like it means but then was turned into a funny joke in NY and NJ. Started around the summer of 2002 by a kid in south NJ. Saying it is most of the time meaningless and is meant to be oddly funny. The phrase "give me a dollar" is funny because hardly no one ever says that or ever will to be serious.
You now hear "Give me a dollar." in middle schools and spoken by bored teenagers throughout the northeast of the USA. Another use by saying it is to shut people up.
"Give me a dollar!"
"Give me a dollar, bitch!"
There are many other ways of saying it.
12 step recovery jargon referring to someone new who talks about how great life is, now that they'resober. Usually meaning that the person is out of touch with reality.
The new guy seems pretty happy for a dude who has no job, no money and no family. He must be on a pink cloud.