Well, first of all, those are two different questions. The answer to the second one, at least, is “yes”; the former? I’m not so sure.
We’re already at a point where there is so much Stuff in the world it’s impossible to keep on top of it all. Whatever media you’re into, be it books, movies, TV shows, music or games, there’s enough Stuff out there to keep you entertained probably for the rest of your life in just one of those formats, let alone if you, like most people, spread your time between several. Even if you spend your time focusing entirely on one genre within a single medium, you’ll never get to the bottom of the pile. You’ll never “finish” culture. You’ll never see everything there is to see.
Depending on your outlook, this is either a fantastic thing or incredibly depressing news. For many, there’s a degree of “shame” over not having caught up on things that are supposedly “canonical” or “essential” for everyone to have read/seen/played/whatever. The very term “pile of shame” (from which the Squadron of Shame takes its name) is used to refer to one’s backlog of entertainment that has been purchased but not consumed — or, in some cases, the definition is stretched a little to include Stuff that the owner of said pile intends to consume at some point in the future, but perhaps hasn’t quite got around to just yet.
With books, it’s fine. Books are passed down from generation to generation; republished and republished. Today, we can keep a book alive forever by converting it to a digital format and scattering it to the four corners of the Internet. Sure, you lose some of the joy of turning paper pages and that distinctive musty smell they have, but at least the important bit — that’s the work printed on those pages, lest you forget — is immortalised. You can read it on your computer; on your tablet device; on your e-reader; on your phone. You can annotate it and share your thoughts with other people around the world in an instant. Books are just fine.
Music, too, has proven itself to be pretty timeless over the years — for the most part, anyway. Throughout history there has been plenty of “disposable” music, but the true greats endure for years. Look how long the works of Bach and Mozart have lasted — people are still listening to, performing and studying these pieces hundreds of years after they were first composed. In more recent years, look at how the music of artists such as Elvis Presley and the Beatles is still interesting and relevant today. In very recent years… well, it remains to be seen which artists (if any) will leave a lasting legacy on culture, but there will almost certainly be some. (And if there’s any justice, it won’t be anyone who has ever won or been involved with The X-Factor.)
Movies, too, have become increasingly timeless with the improvements in technology over the years. While once a movie only lasted as long as the medium on which it was physically printed, now, like books, we can archive and keep movies forever. Sure, some moviemaking techniques now look antiquated and are unpalatable to modern audiences, but those truly interested in the full history of the medium can trawl back as far as they wish and see how it has developed.
Games, though, are arguably a bit more tricky, as they have an inherent “expiry date” due to the numerous proprietary technologies involved. While emulation technology is getting better all the time, it’s still not perfect, and the legal grey areas surrounding it make it something that some people prefer to shy away from altogether. When you consider “PC” games, too, there’s even titles that are ostensibly on the same platform that will no longer run on more modern technology. Fortunately, there are places like GOG.com who aim to keep these titles alive for modern audiences, but eventually even their remastered, tweaked versions will “expire” as technology makes the next big leap forward. What happens when computers become wearable and we don’t use TVs any more? Will we still be able to play classic titles designed for the flat screen?
With all this, it’s easy to wonder how you can possibly get through all those things that you’re “supposed” to watch/read/see. The answer is surprisingly simple: don’t. Accept the fact that you’re never going to read Great Expectations; you’re never going to see Citizen Kane; you’re never going to listen to anything by The Smiths; you’re never going to get caught up on the Assassin’s Creed series. Cherry-pick the stuff you’re interested in, finish what you start, and don’t feel obliged to jump in to things just because they’re brand new and everyone is talking about them right now. Get to them when you have time to appreciate them rather than rushing through them in the ultimately futile attempt to feel “relevant”.
Crucially, enjoy (or at least appreciate) the culture you consume, whatever medium it’s in. Your tastes are your own, and no-one has the right to try and change them. People can share their own opinions, sure, and these may help sway your thoughts one way or the other, but ultimately your feelings about the things you like and dislike are entirely up to you. There’s no “correct” opinion; no gold standard of cultural awareness you need to aspire to; no “checklist” to complete. The sooner you recognise this fact, the sooner you can get on with working your way through that “pile of shame” — because there’s some great stuff in there that you haven’t discovered yet. And the stuff that is shiny and new right now will still be here in a few years time.
Take your time. Enjoy it. It’s the least you can do for the people who have invested their time, money, blood, sweat and tears into entertaining you.