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Sin and Syntax: How to Craft Wicked Good Prose

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Today’s writers need more spunk than Strunk: whether it's the Great American e-mail, Madison Avenue advertising, or Grammy Award-winning rap lyrics, memorable writing must jump off the page. Copy veteran Constance Hale is on a mission to make creative communication, both the lyrical and the unlawful, an option for everyone.

With its crisp, witty tone, Sin and Syntax covers grammar’s ground rules while revealing countless unconventional syntax secrets (such as how to use—Gasp!—interjections or when to pepper your prose with slang) that make for sinfully good writing. Discover how to:

*Distinguish between words that are “pearls” and words that are “potatoes”

* Avoid “couch potato thinking” and “commitment phobia” when choosing verbs

* Use literary devices such as onomatopoeia, alliteration, and metaphor (and understand what you're doing)

Everyone needs to know how to write stylish prose—students, professionals, and seasoned writers alike. Whether you’re writing to sell, shock, or just sing, Sin and Syntax is the guide you need to improve your command of the English language.

320 pages, Paperback

First published January 1, 1999

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Constance Hale

13 books45 followers

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5 stars
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487 (21%)
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43 (1%)
Displaying 1 - 30 of 246 reviews
Profile Image for Leslie.
142 reviews
March 8, 2008
Much better than The Transitive Vampire, I think. I'd give it more stars, but to do so with a grammar book would be to offer my inner dork far more exposure than I'm comfortable with.

I'm sorry; I mean, "far more than that with which I am comfortable."
Profile Image for Jennifer Sommersby.
Author 5 books318 followers
February 25, 2011
~Reprint from March 2006~

NONFICTION BOOK REVIEW
© Jenn Sommersby Young ~ 2006-2011


SIN AND SYNTAX: How to Craft Wickedly Effective Prose
by Constance Hale
Pub. Broadway
ISBN 0767903099 / 978-0767903097
2011 update: available for Kindle

There are three absolutes for the reading writer upon his/her decision to ingest Constance Hale’s Sin and Syntax:

(1) Buy your own copy. Do not borrow the library’s edition, my friend, because you will not be able to resist the urge to dog-ear, highlight, scribble, or underline the imperatives dished out as canapés before the brandy. Wordsmiths rejoice and pedants repent, Hale lays out the rules and then rips wheelies all over them.

(2) Read through the book once, allowing your pen to merely fondle the text, consenting to only sporadic gratification with the occasional “*” or “!” Savor the book. Force yourself to pay attention. Don’t be scared or intimidated by Hale’s genius. (Thank heavens there is SOMEONE who understands direct objects, participles, dangling whatzits and thingamajigs). And don’t get caught up on the sentence diagramming stuff or else you might scurry away in terror, leaving your poor pen unfulfilled and frustrated.

(3) Read through a second time and take as many notes as possible before writer’s cramp tangles your fingers. Your pen will bask in the afterglow and might even buy you dinner.

Adroitly constructing her tower block by block, Hale pours the foundation in the sections she calls Bones (a bit of a remedial in grammar school tedium) and Flesh (explaining the connection between the grammar and the prose). But if you snooze, you lose. Hale quickly moves past the snore-a-thon “sermonettes” and dives headlong into the power tools you need to fortify your writing, progressing ever onward and upward to the higher stratum that will house the plumbing and ventilation systems of colorful, imaginative prose.

Hale is a stylistic seductress. The most delicious pieces of each chapter, Cardinal Sins and Carnal Pleasures (honestly, who could resist flipping past the teachy-preachy parts to sneak a peek into the book’s naughty bits?) give context to the earlier lessons by exploiting real world examples of bumbled goober-speak. One of Hale’s favorite targets is President Bush Sr., though she doesn’t discriminate—politicos, academics, and pompous “purple prose” authors are fair game. And once she demonstrates why, it becomes so obvious! Hale warns against treading in “The Danger Zone” the Stuffed Shirts seem to frequent, or you’re risking grammatically inept, slobbery writing—and that’ll do nuthin’ but make yuh sound dumb (or Texan).

But Hale doesn’t just make fun of stumbling speakers and ballooned blowhards. She regularly injects examples of Mark Twain’s spirited prose to illustrate her maxims, inducing a few ‘So-that’s-what-she-means!’ sorta moments. Even Thoreau was a wordy fella and often mucked through six or seven rewrites before lighting on a final version. “You’d be surprised how little you need to get your points across. Strip sentences down. Clear out the clutter,” Hale writes. ‘Nuff said.

Hale dispels some common controversies in written English (Never end a sentence with a preposition, Never split infinitives) and shovels advice on the proper use of grammatical Malvolios (who vs. whom, bad vs. badly, and the English preoccupation with and chronic abuse of the word ‘like’). Though she diagrams sentences with wild abandon and laces the boudoir with antecedents, high energy verbs, and saucy nouns, Hale’s kindler, gentler side entices writers to find the Music, Voice, Lyricism, Melody, and Rhythm in their work. Grammatical accuracy, while a noble objective, should not overrule the natural voice and rhythm in your writing, especially if your characters speak in dialects or distinctive language sets.

If I had more room, I would eagerly compile lists of Hale’s Do’s and Don’ts, the words to politely avoid and words to torch at all costs, and the multiple examples of beauty risen from the swamps. The writer who absorbs Hale’s opus will, at first, wrestle in fits and starts with old habits fighting for their last sucks of oxygen. Let them suffocate. Sin and Syntax is a style manual for the modern writer, a diuretic for written bloat, preoccupied with a sole objective: truth in prose.



Profile Image for Rose.
1,896 reviews1,068 followers
July 4, 2013
Initial reaction: This was definitely well worth the purchase. Considering this takes apart prose piece by piece for function, it's definitely well worth using to see trouble spots in one's edits, as well as how to enhance the prose while breaking a few rules.

Full review:

I'm really glad I picked up Constance Hale's "Sin and Syntax" because I think its a wonderful examination into how the parts of a sentence contribute to the strengths in one's writing, and not only shows the rules for what you can do with your prose grammatically, but also shows where you can bend and break the rules and still have an effective way of drawing your audience into the narrative. Hale cites several helpful examples and I especially liked her expansion on nouns, verbs, and adjectives in terms of how to best punctuate the narrative using them. There are expansions on adverbs, subjects and predicates, prepositions, conjunctions, simple sentences, cadence, voice, among other dimensions that contribute to the narrative you create. I think of this as an immensely valuable resource for writers, and would highly recommend perusing it.

Overall score: 5/5
Profile Image for Emma Sea.
2,198 reviews1,123 followers
Shelved as 'dnf'
February 11, 2014
Quit at page 69.

The self conscious "hippest grammar guide ever" tone pissed me right off.

The examples of poor writing were taken from politicians and academics. Talk about going for the low-hanging fruit.

The examples of good writing I didn't like all that much. The habit of embolding words all through the examples irritated me.

Might have got better: can't be bothered waiting to see.
Profile Image for Marissa van Uden.
45 reviews24 followers
May 2, 2017
"Capturing the zing of conversation requires attentive listening and painstaking revision. It comes from connection,
from the narrator subtly reaching out to the reader and saying, 'We’re in this together.'”

Sin and Syntax: How to Craft Wicked Good Prose, by Constance Hale, is one of those rare grammar guides you can take pleasure in reading front to back because it’s so engaging, witty, and illuminating.

I own plenty of grammar manuals, but this is a far more inspiring creature that goes beyond just the rules. It teaches not only how the cogs and inner devices of sentences work, but how they can be fitted together to create beauty, suspense, and drama.

“Phrases can build grace into sentences. Taut declarations lend clarity, but too many of them can start to sound like a Dick-and-Jane story. A strategically placed phrase can turn a staccato burst into a more lyrical sentence. This is what we mean by ‘turning a phrase’ — using our command of language and mastery of the rhythms of a sentence to affect style as well as substance.”

“Sometimes we don’t so much want a seamless flow, or a drum of random ideas punctuated with commas and ellipses, but rather hard pauses, high tension, urgent twists and turns. Then we bring in subordinate clauses.”

Just like with everything else, it takes a lyricist to reveal the Truth: metaphors just fit better into the human mind.

For example, compare these definitions from the Chicago Manual of Style (AKA the “editor’s bible”) with those from Sin and Syntax (the self-described “hip bible and essential covenant for crafting stylish prose”). This is not to say the CMS is bad; I couldn't be without it -- but it has a different purpose. It's an operating manual for editors, whereas S&S is an ode to grammar for writers and readers too.

Pronouns:

"A pronoun is a word used as a substitute for a noun or, sometimes, another pronoun." (CMS)

“Pronouns are proxies for nouns. They stand in willingly when nouns don’t want to hang around sounding repetitive.” (S&S)

Adjectives:

"An adjective is a word that modifies a noun or pronoun; it is often called a “describing word.” An adjective tells you what sort, how many, how large or small, whose, and so on." (CMS)

“Adjectives are consorts, never attending a party alone, preferring to hook themselves on the arm of a sturdy noun. Adjectives embellish their companions, defining the qualities of the person, place, or thing they’re escorting, and sharing relevant details whenever possible.” (SMS)

Verbs:

“A verb denotes the performance or occurrence of an action or the existence of a condition or a state of being, such as an emotion. … The verb is the most essential part of speech—the only one that can express a thought by itself (with the subject understood).” (CMS)

"[Verbs] add drama to a random grouping of other words, producing an event, a happening, a moment to remember. And they kick-start sentences: without them, words would simply cluster together in suspended animation, waiting for something to click.” (S&S)

Sin and Syntax is divided into three parts: WORDS, SENTENCES, and MUSIC. The first two parts deal with the anatomy of language, while the last part unravels the secrets of melody, rhythm, and in a writer’s voice.

I love that Hale uses examples from how humans actually speak in Modern Day as well as well as the more traditional prose of the past, which is what many of the more prescriptive grammar books concentrate on. Hale happily uses examples from everything from the Bible to WIRED magazine and Twitter posts to illustrate the playfulness of how we use words. She doesn’t shun traditional grammar at all, but incorporates everything to give a wider-than-usual view.

There are some great passages on editing and revising too. She did a lot of research to find out how writers actually hone their manuscripts; for example, she pored over Mark Twain’s draft manuscripts preserved in a library to analyse which words he crossed out and what he replaced them with, and then explained why he might have made these choices.

Since I read Sin and Syntax, I’ve been enjoying reading a lot more and just listening to people talk too; it's helped me appreciate even more deeply why people say what they do and the alchemy of language. I highly recommend this book not just for editors and writers, but for readers too... and anyone who loves the art of conversation. Basically, humans should own this book.

Original post at my blog: http://www.marissavu.com/2013/12/sin-...
Profile Image for Jeff.
Author 4 books460 followers
January 21, 2008
This isn't your traditional how-to book for writers. Rather, it's a meditation on the role of grammar and diction in all prose--and it's a really good one. These sorts of books are only as good as the example passages selected, and here we get some very obscure, very spot on stuff (as opposed to a lot of how-tos, which copy the last page of Sun Also Rises and basically say, "This is how to write--now go do it!") Sin & Syntax really changes the way you think about stringing words together, whether you're writing a novel or a thank you letter to Grandma for those birthday socks...
Profile Image for Roni Loren.
Author 46 books3,445 followers
July 30, 2013
Even if you feel you have a good handle on grammar, this book is worth a read. If for nothing else, read it for the chapters on Voice, Lyricism, Rhythm, and Melody and for the fantastic examples of beautiful writing given throughout the book. This book will inspire you to work harder on your writing, to choose words with more thought, and to pay attention to the music of your prose. I plan to keep this one on my shelf.
Profile Image for Ginger Bensman.
Author 2 books60 followers
February 13, 2016
Sin and Syntax is a perfect book for writers pondering the mechanics and structure of grammar and how best to employ "the rules" (or not) to get to the voice, clarity, flow in their prose. It's a rare book on grammar--written with wit and elegance.
Profile Image for Shannon.
Author 1 book11 followers
August 14, 2011
Dangling modifiers. Loose pronouns. Mixed metaphors. Sentence fragments . . . aw crap.

Whatever your sin, Sin and Syntax is an all-purpose grammar guide that helps not only to improve your grammar but also to polish your prose.

Constance Hale divides her book into three sections: words, sentences, and music. In words, she defines the fundamental building blocks of grammar (nouns, verbs, prepositions, etc.). In sentences, she teaches sentence mechanics and variation. In music, she explains how to add verve to your writing by experimenting with techniques such as assonance, metaphor, and beat.

Her book, however, is not simply about correcting wrongs. Hale informs writers when you can break the rules and when you look illiterate when you do. Putting prepositions at the end of the sentence? Not a big deal. Peppering foreign words into your story? Sure, just don't go crazy. Nouning verbs and verbing nouns? We have a bit of a problem here.

Hale did her homework. She provides extensive examples from politicians and writers to illustrate her concepts. She references numerous other style guides and also provides a handy list of them in the appendix. Most importantly, however, anyone can benefit from reading her book. She writes at a level that's easy enough for the grammatically-challenged to understand, but she also explains advanced material that's still useful to experienced writers. She doesn't delve too deeply into grammar terminology; she focuses her energies on improving your style all-around.

Frank, clear, and amusing, Sin and Syntax is one of the best grammar guides when it comes to perfecting your craft.
Profile Image for Rhiannon Root.
247 reviews6 followers
July 17, 2020
Content warning: Racial slurs, anti-gay slur, domestic abuse

The third season of “The Golden Girls” features an episode called “Dorothy’s New Friend” and in it, Blanche remarks about Barbara (the new friend) that “she cares more about words than she does people.”

That’s how reading “Sin and Syntax” by Constance Hale read, the book doesn’t care about people and it only cares about words. I don’t know the author, I know little about her beyond the author blurb at the back and the contents of the book. I don’t know if there are other editions and the problems I’m going to talk about have been fixed. I can only look at what’s in front of me and analyze that.

This book not once, but three times has the n-word in it. Twice it’s part of a quote, the other it’s in an essay’s title.

Three times on pages 36, 200 and 253.

The book also quotes an example of European slang for a cigarette that also happens to be an anti-gay slur in the U.S. on page 205. (You know, where the book is being published.)

Hale also references a famous journalism lede by Edna Buchanan where in a wife kills her husband and calls it a “lover’s spat” on 159.

What in the actual fuck?

There’s no warning that this kind of language will be used in each instance. It comes out of nowhere and Hale doesn’t even bother to dash it out.

Before anyone jumps in to say, “But these were all quotes! It’s fine!”

It’s not fine. It’s really not. I’ve read more than a few grammar guides and this is the only time I’ve ever encountered this problem. These are unforced errors. This is not OK.

“But it was published in 1999! That was so long ago! Why do you care?”

Do you mean to tell me that a language professional, one who has an advanced degree from an ivy league university couldn’t possibly come up with other examples without offensive slurs? Do you mean to tell me she doesn’t know any better? Do you mean to tell me that the English language is SO limited that there weren’t any other examples she could have used?

Bullshit.

I’m angry and disgusted. Do better.
Profile Image for Tracie Hall.
696 reviews8 followers
August 8, 2016
I picked this up at a used book sale because I recently finished a MOOC class on grammar and, although I passed with flying colors—oh, I think Constance (author) would suggest I rethink that too oft used phrase…hmm, I passed with aplomb, I didn’t feel like I could by any means teach the subject…so thought this title sounded like a fun way to keep going. I was write! Errr, “Right”! (Now you’re wondering how I passed at all?) This book has it all, and if you didn’t think a book on grammar could be entertaining (as well as instructive), read this one.
Sample? OK, here’s one of many illustrative quotes complete with quippy explanation of the error. This passage is from a section called “Dangling Doozies”:

“Remember, participles exist so that verbs can modify nouns. Dangling participles are adjectival phrases that have come unmoored from the nouns they are supposed to modify and instead modify the nearest noun they can find. Here’s a dangling participle reprinted in the "New Yorker" as a space filler:
In San Diego, the “in” place for years has been McDini’s for corned beef. Thinly sliced and heaped on rye, corned beef lovers won’t be disappointed.”
When was the last time you were thinly sliced and heaped on rye?”

I get that a grammar book probably isn’t your first choice for light summer reading, but if you do happen to enjoy the many quirks of the English language, this is a good one to turn to.
1 review2 followers
May 7, 2012
I consider myself to be a reasonably knowledgeable grammarian; however, my philosophy on the subject is you can never brush up too much. So, with the disclaimer that I happen to find this subject matter interesting most of the time, I will move on to specifics of this book. I'd like to think even those less interested in grammar would find this work at least somewhat enjoyable. If you're looking for technical answers, you'll find them. Hale breaks the topic down into words (the parts of speech), sentences, and music (voice, lyricism, melody, and rhythm), and each subsection is further broken down into the bones (simple keys to grammar), the flesh (lessons on writing), the Cardinal Sins (errors that true grammarians will recognize as those mistakes people make that make us grind our teeth), and the Cardinal Pleasures. This last segment borrows from some of the finest examples of writing I've ever had the pleasure of reading, over half of which I'd never before been exposed to. Whether you have grammar questions you've never been able to fully explain before (I'm feeling much better about using "that" and "which" correctly) or you just derive visceral pleasure from the sentences "Who's and it's are contractions of who is and it is. Learn this or die.", you will find much to make reading Sin and Syntax worth your while.
Profile Image for Laura (Book Scrounger).
753 reviews49 followers
September 4, 2019
3.5 stars

Good reference. I read it through from beginning to end because that's how I roll, but it will be good to look back on for reminders about specific rules of syntax. Many examples from media and literature are included for the correct and incorrect ways to use parts of speech and other aspects of writing. I think the last few chapters, on more nebulous ideas such as "music" and "voice" were especially helpful and more fun to read.
Profile Image for Emily.
167 reviews1 follower
April 16, 2018
I think this book would be incredibly helpful for someone who's just getting into writing or even for old pros who just don't know why some things sound right and others don't. The foundational information about grammar was kind of re-hashing for me because I've studied grammar for years, but it's good information, and it's presented in a way that builds logically and is relatively easy to stay engaged. With helpful examples and especially helpful writing prompts, this book walks writers through what the English language is capable of, and it's always good to be reminded of that, even for a linguaphile like me.

The chapters are structured through the following headers: bones, flesh, cardinal sins, carnal pleasures, and catechism. The bones sections teach the basics of the part of speech or grammatical part. The flesh teaches how to properly use it. Cardinal sins teaches how it's often misused. Carnal pleasures teaches how it's used well. Catechism provides a writing prompt or a challenge to test your understanding of the principles covered in the chapter. This method creates repetition and helps you really understand what's being taught.

If you're going to read a book on grammar and writing, this is a good one to read.
Profile Image for Cameron Quinn.
Author 5 books10 followers
May 4, 2021
Initially engaging, but ultimately not a useful read.

Hale's ridicule of the singular "they" stung, but I was willing to give some leniency on behalf of the 20+ since publication (not great then; inexcusable TERF rhetoric today). However, the frequent, casual inclusion of racial slurs in passages analyzed for unrelated reasons? I can't fathom a justification - then or now - with billions of other published words to choose from.

(I initially gave it a second star, and then I realized I was listening to the "revised and edited" 2021 edition! In addition to being unkind, the text is outright inaccurate.)
Profile Image for window.
506 reviews33 followers
August 19, 2009
For a grammar book, this was actually entertaining! I know, hard to believe but true. A good portion of the book discusses various parts of speech and their correct grammatical use; however, there is also a lot of information on how to improve the clarity and quality of your prose. Trim down those sentences bloated with adverbs and adjectives and trade out those flabby verbs for stronger ones - your writing will be the better for it!
Profile Image for Skylar L. Primm.
446 reviews10 followers
July 27, 2015
Constance Hale is an engaging author, and her irreverent take on grammar is a delight to read. I felt a little bored in the middle (sentences, phrases, etc.), but it starts and ends strong. Hale's advice has already helped to improve my own prose, and I'm sure it will help that of my students, as well.
Profile Image for Jen Compan (Doucette) .
294 reviews3 followers
July 27, 2015
Delightful grammar text? Not an oxymoron.

Constance Hale's overview and insight into the basic elements of language will long impact my writing and the way I read my students' writing.

Simply delightful.
Profile Image for Tammy V.
297 reviews22 followers
June 15, 2022
ok. Maybe 2.5.

Read this book for a 16-week class. About half-way through I was over it (but continued the class so continued browsing the chapters all.the.way.through.).

I think we all need a good review of syntax if we are writers. I discovered that some things about diagraming have changed since I learned it (very well evidently since I was the only one in class that really understood diagramming), or maybe in 5th grade they only take you so far. Judging by others' responses, much of what was offered was not explanatory enough for everyone to be able to demonstrate they understood what clause are, for instance, and how they are used. From the chapter Subject and Predicate to the end of the book we have Simple Sentences (where I was introduced to "static verbs" - why here and not in the chapter titled Verbs. And when were they invented because I have *never* heard of them before), Phrases and Clauses, Length and Tone, Melody, Rhythm, Lyricism, Voice and much much much repetition.

I hope there are better books out there on syntax. I would love for your to share your favorite book on syntax if you have one.
Profile Image for Mark.
198 reviews
May 19, 2020
An exceptional highly readable book about clarity and grammar. Hale is the former WIRED magazine editor. the book touches on clarity, and has an underlying theme of how clear concise writing is spiked to death by committee, or overzealous editors. The writing examples are not only from WIRED, but from poetry and literature from Shakespeare and Walt Whitman to the present day (or at least 1999 as the modern day). The sections about adverbs, the subject/predicate, and writing rhythm are exceptional. It's a brisk read at 266 pages (not including the appendix), wide margins and plenty of subheadings. Hale is very funny without over doing it

(Overall: 4.5 stars)
My only disappointment, this book was published in 1999. In tech think, that's 1000 years ago. is that there is not an updated digital version of this book. Language needs saviors now more than ever.
Profile Image for Ben.
624 reviews1 follower
May 12, 2018
A nice refresher of grammar. I don't remember much of what grammar I was taught in grade school. This book took me through the basics in an entertaining way.
Profile Image for Laura.
147 reviews2 followers
Read
January 31, 2021
If I hadn't taken a grammar class within the last year, I think this would have been more engaging and helpful, but, as I have, it was a big of a slog because most of its topics were fresh in my head. The structure of this book is intriguing but didn't really work for me. It's also very clearly of its time (1999), as evidenced by some of the examples used, which I found a bit distracting.
Profile Image for Megan H.
30 reviews1 follower
September 23, 2017
I learned more grammar from this book than I did through all of school, I think. A helpful guide for writers to help learn not only how to craft a world but pay attention to language itself.
Profile Image for Marta.
166 reviews14 followers
April 26, 2016
Writing well, both grammatically and with flair, is an on-going process and can always be improved. I have a degree in English and aced a grammar diagramming class (both decades ago), but I find that I forget quite a bit and need to continue to renew my knowledge. Also, trends in what is grammatically in and out tend to change over time. I tend to read and reread writing books every few years and have just started this cycle.

Some points of grammar tend to be highly personal (I wonder if there have ever been any duels fought over grammar) and I thought Hale carefully covered all the conventional and disputed points. I liked how at the same time as describing the building blocks of the parts of grammar, she illustrated that each part is important and can make a sentence thrilling or a dud. The final section, "Music" pulls it all together like all the parts of the orchestra playing really well together. This part required more attention because of the often subtle distinctions.

So I would recommend this book both to the novice and the experienced writer and/or lover of good writing. It is easy to forget the finer points (okay, or even some of the basics) and I'm sure in rereading this work in the future, I'll have some new aha moments.
Profile Image for Graham.
1,309 reviews64 followers
March 30, 2012
I always remember a piece of advice in Stephen King's ON WRITING, which I read a good few years ago: King recommends that writers get themselves a "writer's toolbox" of skillsets, reference books etc. that they can fall back on and use to enhance their trade.

Ever since, I've been keeping an eye out for really good guides to the nitty-gritties of writing: namely, spelling, punctuation and grammar. SIN AND SYNTAX may well be one of the best of those guides.

The first and foremost thing about this book is that it's an entertaining read. No dry, academic textbook stuff here (and believe me, I've read my share of them). Hale is a witty and involving author, and she makes a potentially unengaging/uninteresting subject positively zing at times.

The book is split into short, manageable chunks that make reading - and learning - a breeze. Language is brought to life in all of its wondrous forms, with equal prominence given to Shakespeare and modern-day rap lyrics. You'll learn a lot from reading it.
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