My best advice is to go swatch crazy. Your best red is going to depend on your coloring and what intensity you're really looking for. MAC has some really great reds, but you'll find a pretty large selection across most brands. I'd hit up Sephora or department store counters myself.
I approach this a different way--red is a logistical nightmare. It smears SO easily. So the texture of the lipstick is much more important than with other lipstick.
For me, wine colors are really unflattering, but they may work for you.
Slightly matte reds will stay better than cremes or glosses. MAC's regular lipstick is way too cremey for practical wear. Their 12 hour stuff may work, but I usually stay away from the super long wear with red because it can flake and that is really obvious in a dark color.
I actually do like the texture of Channel lipstick for dark colors. One of my favorites (and less expensive) is Sephora brand long wear--it comes in a tube that looks like thinner Chapstick.
I also like using lip primer for a nice even texture.
I usually wear my red lipstick with a little bit of very neutral eye shadow and somewhat heavy liner. Red lipstick makes my eyes really bright which is fun.
I just got the clinique intense chubby stick in chunkier chili and I really like it. It's red without being too obnoxious but you definitely look like you have color on your lips.