MAC Full Coverage Foundation, MAC Studio Finish Skin Corrector, MAC Pro Longwear, and MAC Studio Fix plus SPF. How bad is the shaddow?
Sometimes a little red or orange lipstick under your foundation /concealer will do the trick.
Benefit erase paste concealer, and Benefit Big Easy Face Perfecter foundation. MAC and Benefit are really good "full coverage" makeups.
I use MAC Pro-Longwear Concealer with Studio FIX Liquid foundation. Then set with Studio FIX Powder. It is good for cover up on an average day. Bad day, I use the Benefit erase paste, Big Easy foundation, and Kate Von D contouring pallet. It'll pretty much cover anything short of a full beard.
If your 5 O'Clock is actually stubble, Pancake is the only real way to kill it. It'll be heavy and it's definitely going to try and clog your pores. So have a really really good facial cleansing routine.
Hope it helps!