I con­fess, I pre­fer Faulkn­er to Hem­ing­way and see noth­ing wrong with long, com­plex sen­tences when they are well-con­struct­ed. But in most non-Faulkn­er writ­ing, they are not. Stream of con­scious­ness is a delib­er­ate effect of care­ful­ly edit­ed prose, not the unre­vised slop of a first draft. In my days as a writ­ing teacher, I’ve read my share of the lat­ter. The Eng­lish teacher’s guide for par­ing down unruly writ­ing resem­bles a new online app called “Hem­ing­way,” which exam­ines writ­ing and grades it on a col­or-cod­ed dif­fi­cul­ty scale. “Hem­ing­way” sug­gests using sim­pler dic­tion, edit­ing out adverbs in favor of stronger verbs, and elim­i­nat­ing pas­sive voice. It promis­es to make your writ­ing like that of the famous Amer­i­can min­i­mal­ist, “strong and clear.”

Of course I couldn’t resist run­ning the above para­graph through Hem­ing­way. It received a score of 11—merely “O.K.” It sug­gest­ed that I change the pas­sive in sen­tence one and remove “care­ful­ly” from the fourth sen­tence (I declined), and it iden­ti­fied “unruly” as an adverb (it is not). Like all forms of advice, it pays to use your own judg­ment before apply­ing whole­sale. Nev­er­the­less, the sug­ges­tion to stream­line and sim­pli­fy for clarity’s sake is a gen­er­al rule worth heed­ing more often than not. Broth­ers Adam and Ben Long, cre­ators of the app, real­ized that their “sen­tences often grow long to the point that they became dif­fi­cult to read.” It hap­pens to every­one, ama­teur and pro­fes­sion­al alike. The app sug­gests writ­ing that scores a Grade 10 or below is “bold and clear.” Writ­ing above this mea­sure is “hard” or “very hard” to read. Which prompts the inevitable ques­tion: How does Hem­ing­way him­self score in the Hem­ing­way app?

In a blog post yes­ter­day for The New York­er, Ian Crouch ran a few of the master’s pas­sages through the online edit­ing tool (a con­cept akin to John Malkovich enter­ing John Malkovich’s head). The open­ing para­graph of “A Clean, Well-Light­ed Place” received a score of 15. Hemingway’s descrip­tion of Romero the bull­fight­er from The Sun Also Ris­es also “breaks sev­er­al of the Hem­ing­way rules” with its use of pas­sive voice and extra­ne­ous adverbs. Does this mean even Hem­ing­way falls short of the ide­al? Or only that writ­ing rules exist to be bro­ken? Both, per­haps, and nei­ther. Style is as elu­sive as gram­mar is con­strict­ing, and both are mas­tered only through end­less prac­tice. Will “Hem­ing­way” turn you into Hem­ing­way? No. Will it make you a bet­ter writer? Maybe. But only, I’d sug­gest, inas­much as you learn when to accept and when to ignore its advice.

Relat­ed Con­tent:

Sev­en Tips From Ernest Hem­ing­way on How to Write Fic­tion

Jack Ker­ouac Lists 9 Essen­tials for Writ­ing Spon­ta­neous Prose

Crime Writer Elmore Leonard Pro­vides 13 Writ­ing Tips for Aspir­ing Writ­ers

Josh Jones is a writer and musi­cian based in Durham, NC. Fol­low him at @jdmagness

Every­one I know has a list of least-favorite words. For var­i­ous rea­sons, “moist” always seems to make the top three. But per­haps it takes a writer—someone who savors the sounds, tex­tures, and his­to­ries of pecu­liar words—to com­pile a list of their most-favorites. A few I’ve placed in keep­sake box­es over the years—little cor­ru­gat­ed min­er­als that remind me of what words can do: “palaver,” “obdu­rate,” “crevasse,” “super­fe­cund”….

I could go on, but it’s cer­tain­ly not my list you’ve come for. You’re read­ing, I sus­pect, because you well know the con­sum­mate care and atten­tion David Fos­ter Wal­lace lav­ished on his prose—his rep­u­ta­tion as a smith of end­less cre­ativ­i­ty who, Alex Ross wrote in a series of McSweeney’s trib­utes, spent his time “keen­ly observ­ing, forg­ing acronyms, rean­i­mat­ing life­less OED entries, and cre­at­ing sen­tences that make us spit out our beer.”

Ross’s men­tion of the Oxford Eng­lish Dic­tio­nary, that ven­er­a­ble repos­i­to­ry of the vast breadth and depth of writ­ten Eng­lish (sad­ly kept behind a pay­wall), helps us appre­ci­ate Wallace’s list, which fea­tures such archa­ic adverbs as “mau­gre” (“in spite of, notwith­stand­ing”) and obscure adjec­tives as “lacinate” (“fringed”). Who has read, much less writ­ten, the Anglo-Sax­on “ruck” (“a mul­ti­tude of peo­ple mixed togeth­er”)? And while the equal­ly rock-hard, mono­syl­lab­ic “wrack” is famil­iar, I have not before encoun­tered the love­ly “prima­para” (“woman who’s preg­nant for the first time”).

Anoth­er page of Wallace’s list (above—click images to enlarge) includes such trea­sures as “taran­tism,” a “dis­or­der where you have an uncon­trol­lable need to dance,” and “sci­olism,” a “pre­ten­tious air of schol­ar­ship; super­fi­cial knowl­edga­bil­i­ty.” While it is true that Wal­lace has been accused of the lat­ter, I do not think this is a com­pe­tent judg­ment. Instead, I would describe him with anoth­er of my favorite words—“amateur”—not at all, of course, in the sense of an unpaid or unskilled begin­ner, but rather, as it meant in French, a “devot­ed lover” of the Eng­lish lan­guage.

These pages come to us from Lists of Note (and the Har­ry Ran­som Cen­ter at UT-Austin), who writes that they are “just two pages from the hun­dreds of word lists he amassed over the years.” Per­haps one day we’ll see a pub­lished edi­tion of David Fos­ter Wallace’s favorite words. For the nonce, head on over to Lists of Note to see this min­im of his lex­i­con tran­scribed.

Relat­ed Con­tent:

David Fos­ter Wallace’s Love of Lan­guage Revealed by the Books in His Per­son­al Library

David Fos­ter Wal­lace Breaks Down Five Com­mon Word Usage Mis­takes in Eng­lish

David Fos­ter Wallace’s 1994 Syl­labus: How to Teach Seri­ous Lit­er­a­ture with Light­weight Books

30 Free Essays & Sto­ries by David Fos­ter Wal­lace on the Web

Josh Jones is a writer and musi­cian based in Durham, NC. Fol­low him at @jdmagness