Pay no attention to the whale. He's a blowhole, and can't help it.

I think you might be packing the weed in too tight. Try breaking it up a bit better before jamming it in there. You're don't want to just have huge blocks, you'll want it rather fine - no stems or seeds. Additionally, make sure that you haven't completely sealed one end - that makes it very very difficult to smoke.

Ditch the Backwoods and whatever other ridiculous cigars you've tried. Buy a Padron 4000 maduro.