Meaning
A man from rural Jamaica — the countryside rather than the town — and, warmly, a friendly term of address, roughly 'my brother' or 'my friend'. To hail a fellow as 'countryman' is to greet him with easy fellowship, and the word can carry real pride in country roots and the honest, rooted life of the land, or a gentle tease about being unsophisticated and green to town ways. It belongs to the whole town-versus-country feeling of Jamaican life, and as a greeting it warmly claims another as one of one's own.
Examples
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Wah gwaan, countryman?
What's going on, my friend?
A warm greeting, not necessarily about where the person is from.
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Him a true countryman, grow pon di land.
He's a real country man, raised on the land.
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Di countryman bring fresh yam come a town.
The country man brought fresh yams to the city.
Origin
A compound of 'country' (rural Jamaica) and 'man'; also the title of a well-known 1982 Jamaican film that spread the word abroad.
How it’s used
As an address it is friendly and inclusive; as a description it marks rural origin, with warmth or light teasing depending on tone.