Doing your homework can be overrated because actually you tend to lose context rather than gain it. Going through a 'Best Albums Of All Time' list or a 'Best Films Of All Time' list can be counterproductive to me. Much better is that your tastes evolve organically, with one thing leading naturally to another i.e. you get into The Clash which subsequently leads you to Joy Division and then Wire and then Sonic Youth and then My Bloody Valentine and then Slowdive and then Cocteau Twins and then Beach House and then The Weeknd etc.
Going throughn 'Best Of' lists becomes boring and unnatural, and you don't even like the albums as much as you hoped because you go in with such high expectations. It is very hard to be blown away when you are told before you even start that this film or record or match is one of the greatest of all time. The first time I watched 6/3/94 was a major disappointment. I watched it again a couple of years later going through AJPW in order and it made much more sense and was incredible, having the combined advantage of lowered expectations and a natural lead in to the match. Rather than putting the DVD in expecting to watch the best match of all time.