It depends on what youre into. his essays like consider the lobster or this is water are pretty literal but still reflective and "deep." infinite jest pale king and brief interviews w hideous men(kinda) are fun but intellectually kind of relentless and difficult if you read it quickly. If you have a lot of time infinite jest is a good intro, but if you don't an essay is prob better.

It sounded boring to me, and it is boring in some sections, but that's also kind of the point? I'll say I bounced off it twice over the years, but when it finally clicked it clicked hard ("rang my cherries" to quote DFW himself describing his description of reading Barthelme for the first time). I do love his essays and short stories (I also have an unhealthy addiction to reading/watching his interviews), and they'll certainly give you a good sense of his concerns and style, but really IJ is its own beast. I say give it a shot, and if you don't vibe with it, keep it on your shelf and try again later. Eventually it will be the right time.