We'll start with Dots (2521 SE Clinton, food 'til 2 am). I often wind up at Dots with friends who are worried about money. The food is greasy and pretty good, but the service is for shit. I'm sure the waitresses are wonderful people, but a little attention and hustle can really reflect in the tip (I don't care how hungover you are). Dots has no windows and it is very dark inside, to the point of you not being able to see your food. Oh, and very smoky, too. So that place sucks.
Next we're off to Holman's (food 'til 1 am weekdays, all night weekends), a bar off of Burnside and SE 28th. The crowd is a mix of hipsters, hicks, and old people. Surprisingly, I find myself eating here quite a bit. The food is super greasy, but great bar food. The Monte Cristo, the Club Sandwich, and the Chicken Fried Steak are all recommended. Killer Long Islands, I might add. There is a non-smoking section and a patio out back. The service is often bad in the non-smoking room. You will probably be forgotten about.
Another place that I actually like is Sweetwater's (3350 SE Morrison, open 'til 1 am on the weekdays, 2 am on the weekends). For some reason I always get resistance when I suggest it. That may have something to do with the endless amounts of reggae and the fact that the food is way overpriced. Caribbean food is the specialty, and it rocks. The Jerk Chicken is a must-have. The side dishes are all vegetarian or vegan and really good. For example, "Smash" is a mashed potato/yam hybrid that is awesome, and the Curried Avocado is worth a try. For appetizers, I recommend Conch Fritters and Fried Plantains. If you think you are a badass, I suggest the Habañero Poppers for a little humbling.
The last place I'll mention is AhSo (720 SE Hawthorne). A weird tanning salon- turned-sushi bar in the Bermuda Triangle. They start serving at 8 pm and are open until 4 am. This place is chock-full of addled strippers, drunk hipsters, and disgruntled service industry types. The selection of sushi is limited, and tailored to the tastes of drunk white people (lots of cream-cheese filling and deep-fried choices). The fish is always fresh, and my impression is that care is actually put into making the food. Far less care, however, is put into waiting on patrons. The place is spendy, but then again, where else are you gonna get good sushi in the middle of the night?