I just can't decide whether I would have gotten along with David Foster Wallace or been annoyed with him, if I had known him in real life. A Supposedly Fun Thing I'll Never do Again (1997) is my second foray into Wallace's writing, since I read Consider the Lobsters sometime last year. And I had a similar reaction to this latest one I read. I loved some parts and some of the essays, but others were a struggle to finish. Since DFW taught at my alma mater, I already have a predilection for him; and when he hits on a topic that I even have a vague interest in (for instance, tennis, which I've never played and I barely know the players or the rules), his honesty, way with words, unique point of view, and attention to detail are mesmerizing. On the other hand, Wallace can come across as a phenomenal snob, and sometimes I can't help but wonder if he's just throwing in large words, name-dropping authors I've never heard of, and using cutesy and unnecessary abbreviations just to show off his great intellect and creativity.*
I most enjoy reading DFW's work when he simply goes somewhere and does something and describes his perceptions and experiences. I really enjoyed reading about the State Fair, the tennis tournament, and the cruise ship experience. I also enjoyed his essay on David Lynch, although I was somewhat hindered by having only seen David Lynch's Mulholland Drive. I would have loved to have DFW explain that movie to me, but alas, it hadn't come out yet and he instead went into detail on a bunch of movies I hadn't seen. Yet even with this lack of knowledge I found DFW's personal fascination with Lynch, his perceptions of a movie set, and his interpretations of Lynch's work engrossing.
Unfortunately, this was not the case for his essay about television and fiction. I think the main problem is that half of what he was talking about was way over my head. Every author and movement he dropped into the book I had never heard of, and DFW did not explain any of them, which made it very difficult and tedious to try to follow his argument. It was also very dated; that particular essay was written in 1993, seventeen years ago. Even most of the commercials and some of the television shows he mentioned I was not familiar with, although I wished that he was still around to comment on all of the reality shows we have now. On the small sections that I could understand, I would still get caught up in it, but my main memory of that essay was of a painful struggle. Also, there was another essay about "the death of the author" or something, which was short and more understandable but one where my main feeling while reading was frustration. I'm a very concrete thinker, so I find obscure philosophical questions that don't have much grounding in reality very annoying.
I think what is so enticing about David Foster Wallace is that he just puts himself out there on the page, faults and all. He'll tell people that he had to psyche himself up to go to the single's bar on the ship, that he thought he was almost as good a tennis player as the pros--until he saw them play, that he's terrified of amusement park rides, and that he's a snob and an asshole. His honesty is not only entertaining but you feel closer to him when he opens up his life, and it makes him more relatable. But at the same time, David Foster Wallace, is wickedly smart, and writes these amazing, eye-opening things about mundane matters, and the combination is rather irresistible.
*As an homage to DFW, I will throw in a couple footnotes as well. During the description of his luxury cruise, David Foster Wallace was unfortunate enough to stumble upon one of my many pet peeves. Wallace mentioned at the end of his cruise, he grossly undertipped the sommelier and another waiter/helper type (I forget who) because he didn't like them; then he gave the head waiter, who had a masters degree in something, and who DFW did like, all the extra money. And this is after DFW repeatedly pointed out how weird it was to have the mostly third-world employees waiting on all the rich Americans, but then he goes and arbitrarily deprives two of them of their salary. It doesn't matter if you don't like them, tip them at least the minimum. I've been in plenty of situations where people started complaining about the service when it came time to determine the tip, but I've never actually been in a situation where the waiter didn't deserve one. In my opinion, it is [almost always] just an excuse to be a cheap bastard.**
**Surprisingly, I have never worked at a tip-based job, so I'm not sure where all this vehemence comes from.