Identify this game please

Cafe Society
#1

Where does this “actual unmodified screenshot” come from?

I’m guessing it’s some computer game or other.
http://www.galactanet.com/comic/99.htm

#2

Earth and Beyond.

#3

I’m a huge fan of Casey and Andy, but I don’t get it.

#4

Well, I’ve never heard of Earth And Beyond, but the joke is obvious - the route takes a huge detour instead of the direct route. Obviously, some flaw in the AI programming.