Here are my picks:
1. The best song to start with: Buy Wyclef Jean's Welcome to Haiti. "Ou Marye" (track 8) is my single favorite song these days, sadly I cannot find it on YouTube but you can download it. Start there. This one also has strong Haitian influence. This is a kind of Haitian rap, with a good video. Here's a super-fun mix of ragga and compas, with Buju Banton and T-Vice.
2. Three groups which are best seen live: Ram, Boukmans Eksperyans, and Tropicana. Tabou Combo is another.
4. The best recent Haitian group and recording: Ti-Coca. I like all their CDs but my favorite is a blue and orange one I bought in Paris which I don't see on Amazon. I think they're better on disc than live.
5. Best Haitian musical star to dance to: Sweet Mickey. For a while he was selling cell phone cards, but he has returned to the world of music.
6. The classic father-figure of Haitian music: Nemours Jean-Baptiste. Try this song on YouTube.
7. The most comprehensive historic collection: Alan Lomax in Haiti, 9 CDs, of highly varying quality but always interesting.
8. Best-known Haitian songstress: Emeline Michel, sometimes called the Joni Mitchell of Haiti. Here she is doing "Many Rivers to Cross."
9. Best Haitian rara collection: That's the noisy. discordant music they play leading up to Carnival. This would be my pick. Overall it's a vibrant genre.
10. What else?: Haitian children's songs are often quite good, Haitian rap I barely know, and Haitian gospel is a vital area, though hard to capture on disc. Here is the Wikipedia entry on Haitian music.
11. Non-Haitian contributors: The group Simbi, a mizak rasin band founded in 1987, is made up of Swedes, who play an exact copy of Haitian voodoo rock.
Some of you may recall the third and fourth sentences in my book Creative Destruction: How Globalization is Changing the World's Cultures (now on Kindle by the way):
"The founder of Kassav, the leading Antillean group in the funky style of zouk, stated: "It's this Haitian imperialism [i.e., the popularity of the groups] that we were rising against when we began Kassav." Governments responded with protective measures to limit the number of Haitian bands in the country."