I think Nite Owl is a great bar in a basement. Therefore of all of the basement bars I have been to it is a four star establishment. I don't think I would really compare it to Broken City or Hop In Brew Pub because those places have food and more than one floor, so don't except that kind of place and you'll be happy.
If you want a nice cozy bar with a great staff, a good liquor selection, and a variety of different events each well then this is the place for you. So far I have only gone in Tuesdays which is the night for live comedy (and sometimes karaoke and sometimes a live band afterwards). Usually it's dead in Tuesdays but it's a great night and a good time to are comedians work through material. I like it because its many of the same guys you will see at Oak Tree or Comedy Monday Night but in a much more intimate setting.
If you're not into comedy Nite Owl is also a great place to get a strong drink and dance on other nights of the week.
The decor is a little interesting with one wall covered in books but that's also a fun conversation starter (I believe the entire World Book from 1986 is on the wall) if you are lacking material on a date night ;-). I find the beer selection to be wanting and expensive with mostly bottles over $7 and only the seasonal Last Best on tap.
All in all, though, its a great place to spend the evening no matter the night you go on.