It's a song of romantic and kindred love about a man reminiscing about the time he left his home, his close friends and his girlfriend to find work elsewhere. He reflects about his close friendships, despite their poverty (he lives in a poor ghetto, namely the "government yards in Trenchtown"). His imminent departure makes his girlfriend cry; and the man comforts her ("little sister don't shed no tear; no woman, no cry" meaning "please don't cry").

The song is from Bob Marley's real life. He assigned the lyrics copyright to his friend so that he could continue to "cook corn meal porridge" for the poor residents.

The song has a political implication, due to its frankness about poverty and its celebration of people's strength in that situation. That's the point of comparing "hypocrits" to the "good people".

The meaning of the repetition of "no woman, no cry" isn't apparent from reading the lyrics. If you listen to the song you'll hear it start as a request (as in "please don't cry") and end as a statement of women's strength (as in "you are so strong you never cry"). Note that the woman is the strong person here: she is being left behind in the ghetto, presumably to keep their home whilst he sends her his earnings.

The multilayered meanings, the subtle messages despite the simple lyrics, the subtle but simple-sounding playing -- all are reasons why this song is still so loved, despite being over 40 years old.