Bobbi Brown Long-Wear Gel Eyeliner will wear the longest, is waterproof and works in the waterline of the eye. But you have to use a brush. Get over it. Yes, it takes more time and yes, you have to practice to get it right but the results are bar none the best.
Oh hey, this is the brush you should use. Yes, it feels like a pitch when the Bobbi girl/gay says it has to be Bobbi, but what they mean is it has to be synthetic. If you use a natural hair brush it will gum up, be difficult to control, and ruin your brush to boot. Bobbi made the brush specifically for the liner, so cough up.
EVERYONE HAS ONE: (but not as good, or way expensive)
The easiest and gentlest way to get your face clean is with a wipe. If these things didn't exist, I would never wash my face before bed. As it is, I rarely wash my face before bed. But you should. Do as I say not as I do I really like Mac Wipes. They are so soft and big and you can get a shit ton of them for $26. I think they have vitamin E and I swear I will buy anything that has E in it..
Also good, but for an oilier skin, Shiseido Pureness Gentle Cleansing Sheets. Although I have dry ass skin and have used them quite a lot with no ill effect. There are only 30 in in here for $17 but they smell real good.
The ones in my bathroom at the moment are Estee Lauder Take It Away Towelettes. Lauder wants me to wash my face with cleanser after I wipe, but I say screw it and go to bed. $17