I am currently obsessed with Dan Clowes.
Once you start filling in the islands there are some basic technical approaches for reorienting your perspective. One of my favorites revolves around the idea that while the past continually recedes, the relationships between historical moments remain relatively intact, so that roughly 15 years will always separate 1995 from both 1980 and 2010, for example. Applying this relatively portable frame to various eras allows you to approximate the maturation and decay of various trends and other cultural entities, not to mention the inflection points around which history appears to speed up or slow down. This in turn liberates the perspective from generational constraints and reinvigorates the past.
For example, when we were children, World War I was still roughly 60 years in the past and its traces occupied a certain stratum in contemporary life, had a certain resonance or echo. Nowadays, World War II occupies the same relative position and (barring outside factors) its reverberations should be diminishing at roughly the same rate. When we were children, the ghost of 1958 was roughly 20 years gone, which means that the world of South Pacific or "Great Balls of Fire" was as present for our parents then as Twin Peaks or "Out of Time" is to us now. The Eisenhower recession ... the 1987 crash ... the credit crunch. Today 1958 is barely relevant but they're remaking Wall Street. In 20 years, where will we be? And so and so forth, adjusting for inflection points of course. If everything else is equal, comic book collecting today should be roughly as mature as stamp collecting was around 1910. (And if it isn't, it points to the presence of previously invisible external forces.) This also has a constructive application, as 1958, for example, can be approximately reconstituted as the dot product of all the historical relationships that constitute 2010, only slid back about a half century and holding constant terms constant.
The effect is similar to the invention of artificial spatial perspective with its web of gazelines. When you start thinking in these terms it gets easier to put scattered historical accounts in their places -- to navigate the otherwise endless sea of time, memory & junk in search of terra that's firma -- and construct your own. Watch pop coagulate, backward through the bobbysoxers, cylinder recordings, vaudeville, Napoleon, nursery rhymes, commedia, vanishing point ("tradition").