This would depend on your definition of what is dark and gloomy is. Blues and folk music are pretty much entirely based on all that is gloomy. Blue brothers - shotgun blues Bob Dylan - I shall be released, and it's all over now baby blue. Jimi Hendrix - the wind cry's Mary Eric Clapton - tears from heaven When I think dark, I think metal. Some of the darkest shit I've heard, Portal. If you can't handle black metal, Danzig and Slayer have a lot of songs that fall into the category of dark music.