I have my eye on a couple of Spider-Man stories. I'm sure I'll get to them eventually. If you want to try Batman, I would suggest going to the library! 
Year One by Frank Miller is probably a good place to start, though I could give you some more recommendations (with more recognizable villains) if you want.
I'd love to read Sam & Max but I doubt I'll find them at the library 
I think I like Batman because he's not super (no "powers") but he's not mundane. Other than Batman, though, I don't think the DC catalogue is interesting at all (I'm sure there are some exeptions). If I do branch out much, I'm sure it will be into Marvel territory. If you could recommend just two trade paperbacks, what would they be?
Yes, Matt, you are the only one. I bet Miller doesn't even like it I thought the whole thing was a hot mess. (Well, the bit about the Flash being stuck in a giant hamster wheel to provide power to the whole country was a cool idea.)
I saw Spider-Man Blue there! But...I didn't get it because I already a bunch of stuff. I'll look again next.
I'm definitely going to read Sandman because I love Neil Gaiman's work, and they do have it at the library. They just never have the first volume there. If it's not available next time I go, I'll put a hold on it.
If it's free, why not 
I'm still missing an NES and N64. actually, but I'm not going to complain. I've missed this 16-bit goodness!
Wow, that sucks. Best of luck of figuring out the best solution. I guess if you're expecting the worst, it can only get better...?
Ah, good ol' Frank Sinatra. Classic
This guy also has a jazzy rendition of the ending theme from Chrono Trigger. You'd probably like that one too
