Given Second City's larger than life reputation, perhaps I was expecting too much. Or maybe the magic of improv (and this is improv style, and I think the scenes may have started as improv, but they're basically all scripted) lies in being in the room. Either way, I'm disappointed. And yes, a lot of the cultural references are from the 90s, but I don't think that's the problem either (unless you're too young to remember the 90s). It's just not very funny. The fun part is hearing the voices of people who went on to make it big, notably Stephen Colbert. The unfun part is that it's really not very funny.
Not a lot to say: There's a magic to informal live theater and improv/comedy. I can imagine this having been a great experience in person, but I'm not sure. On audio though, I found it fell flat. If you're smarting from a firing, you might find more here than I did. Some fun details, but I can't really recommend it.