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It Was The Best Of Sentences, It Was The Worst Of Sentences: A Writer's Guide To Crafting Killer Sentences

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Great writing isn't born, it's built--sentence by sentence. But too many writers--and writing guides--overlook this most important unit. The result? Manuscripts that will never be published and writing careers that will never begin.
In this wickedly humorous manual, language columnist June Casagrande uses grammar and syntax to show exactly what makes some sentences great--and other sentences suck.
With chapters on "Conjunctions That Kill" and "Words Gone Wild," this lighthearted guide is perfect for anyone who's dead serious about writing, from aspiring novelists to nonfiction writers, conscientious students to cheeky literati. So roll up your sleeves and prepare to craft one bold, effective sentence after another. Your readers will thank you.

"From the Trade Paperback edition."

226 pages, Kindle Edition

First published January 1, 2010

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June Casagrande

5 books79 followers

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5 stars
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Displaying 1 - 30 of 178 reviews
Profile Image for Anita.
1,825 reviews39 followers
April 1, 2016
This book is not for everybody. If you are a writer, a grammar snob, word lover, or picky reader this might be for you. It is a reference book disguised as a fun, self-help writing text.
Before you rush out for this one you should know that I spent my last day before vacation looking up the rule for the following scenario: Why do we say: "Turn the television on," but not "Turn on it."? (There is a rule--I found it--and ESL students are always desperate for the rules. I hope someone else asks me about this before I die so I can use this knowledge more than once.) That being said, I found this book delightful, but sometimes above my head. Sort of like grammar calculus. She uses lots of examples from real writers, and explains not only how to edit, but the rules behind it. I also liked how she separated grammar from usage and from style.
She covers all the basics and then goes on to really difficult stuff. Dangling participles, misplaced modifiers, copular verbs (I call them linking verbs) are all discussed thoroughly and wittily. My head was sometimes spinning. That's why it is good to read it a little at a time.
My only bone to pick came on semicolons. She is an anti-semicolonite. She stated her bias up front, and I agree with her. The only reason people use them is to show off grammatically. That is exactly why I teach them. If my students can learn how to use a semicolon, they feel smarter. If they can use them correctly and know that "a lot" is always two words, they are smarter than 80% of the American public.
On the whole I give this book an 85--a good beat, easier to dance to than Warriner's (that old high school grammar book we all hated), but not quite as catchy as Eats Shoots and Leaves (a very fun grammar book). This book has a place on my shelf next to The Elements of Style and The AP Stylebook. Come borrow it when you have those pesky sentences that you can't seem to fix.

Profile Image for Antigone.
542 reviews772 followers
January 11, 2017
Yes, I confess, my eyes crossed. My mind wandered. My will faltered several times. You would think, wouldn't you, that the mechanics of communication would be the one area in which we might expect understandable explanations? I mean, if you're good at this, an expert in the field, you should be able to express the knowledge in an inviting and accessible way, yes? Only no. No one does. No one can. Inscrutability is the order of the day.

Casagrande brings a warm, modern-era tone to the mix. It's clear she wants to calm all fear and lower those walls of resistance. Unfortunately, the science of word organization isn't designed to assist her with this. It's not her fault. It's the fault of whatever sadist got the cheapest of thrills out of labeling the terms of the enterprise. Copular verbs. Participial clauses. Modal auxiliaries. Subordinating conjunctions. (A cruel and calculating creature who, no doubt, went to his grave with a sneer and an arthritic gesticulation.)

As a guide to sentence construction, this is a perfectly satisfactory offering. It's comprehensive, it's informative, and it's kind. Her Appendix 2: Punctuation Basics for Writers is, on its own, well worth the price. I took issue with only one element of the material that is directly attributable to its author, and that was her assertion that the reader was the most important consideration in writing. To quote: "Thy Reader, Thy God." Well, no. I won't agree with that. Comprehension is important. Deifying the reader, in my experience, proves profoundly debilitating in the long run.

That said, if at some point in your writing life you foresee an exchange with an editor? Casagrande's work will give you a fine idea of what you'll encounter there.

Profile Image for Tanu Gill.
574 reviews263 followers
July 12, 2016
It's a fun book. I really loved the author's examples and ways to unsnarl a wonky sentence. I admit there were times I got cross-eyed. But overall, a good read. :-)
Profile Image for J.C..
Author  2 books75 followers
July 8, 2013
Before reading this book I took a grammar course that lasted five months. Yet, what I couldn't understand in that whole five months I was able to comprehend with a lot more ease with this little book. Everything is put in clear terms with plenty of examples, and at the end there's at least three appendixes on grammar, punctuation and word usage that is very useful.

I highly recommend this book not just to creative writers but to anyone who wants to improve their understanding or usage of the sentence.
Profile Image for Thomas Edmund.
999 reviews71 followers
November 4, 2017
Oh God, I need to use all the things I just learned to craft good sentences to review this book!

JK, Casagrande pens an amazing succinct and enjoyable book on the craft of sentences. I particularly liked the chapters on adverbs and semicolons.

At times the learning was hard going and while a shortish piece I took my time to absorb, and I suspect I'll come back to it again for grammar help (darn gerunds are the bane of my life)

Highly recommended for writers of all ilk, and of course those who hate semi-colons
Profile Image for Brenda.
562 reviews27 followers
April 1, 2015
Great little book full of excellent information. I disagree with her regarding semicolons, but everything else in this book I know I will refer to time and again. Especially when I am revising.
Profile Image for Navneet Kaur.
18 reviews5 followers
July 12, 2016
I really liked this book. The author has a way with words that is incomparable. It got a bit too technical for me at some points, but overall, this is one great book. :-)
Profile Image for Kris.
1,425 reviews203 followers
October 4, 2014
Quick, useful, and practical.

Whether you are a teacher, or a tutor, or a student who writes, you need this book. If you write at all in life, you need this book.

Granted, I already knew most of the grammar rules, and grammar is sort of my hobby (it gives me a reason to scold naive students with the rap of a rulebook). So some of these explanations might go over your head. But there's incredibly valuable grammar rules, style advice, and basic writing lessons in here. Know your audience. Write to suit the reader. Get rid of filler words... Great stuff tucked into a tiny volume.

There's a few random (and new?) grammatical names scattered in here that seem overly complicated and pointless, but on the whole this is basic stuff that every writer needs to know. Most people don't place much value on knowing how writing really works, when honestly, come on, it's a part of our everyday lives! Why shouldn't we study and appreciate the nuances of our own words? The way we communicate influences everything in our lives! This book shows the importance of studying language, and how we can get carried away with our ego instead of concentrating on crafting the best sentences possible.

This author is a minimalist when it comes to her own copyediting, and it shows through in her advice. Yet she allows for exceptions and doesn't simply discredit the use of long sentences. I found her practical voice refreshing.

I think everyone needs to take a chapter out of this book to heart at some point.
Profile Image for Miranda Davis.
Author  5 books271 followers
October 24, 2012
Honestly, I didn't know what a verb was until studying a foreign language (damned late 1960's "I'm OK, you're OK" elementary educational experiments) so the whole issue of speaking and writing grammatically passed me by when it would have been painless to learn it. Argh. Fortunately, one woman with a good grip on the gnarly weirdness of English and a compassion for the accrued errors in common parlance has weighed in to help. I voluntarily took myself to my college's Center for Academic Assistance to learn many of the lessons in this book, but not all of them stuck so I am thrilled to have a great, concise generously-illustrated guide to grammar. Of some of the mistakes discussed, I said to myself, 'I knew THAT.' While reading too many others I'm ashamed to say I thought, 'What the hell is wrong with that?' Short of having a grammar nazi review every piece of your writing and explain your own personal grammar problems, this is pretty darn wonderful.

I will enjoy reviewing this to brush up my English. Thank you, Ms. Casagrande. I owe you an apple.
Profile Image for David.
9 reviews
March 7, 2018
Never thought a book about grammar and prose could be a delightful read! I can't put it down.
Profile Image for Lynda Dietz.
57 reviews14 followers
June 28, 2017
I can’t recommend this book strongly enough. Not only is it informative, but it’s presented in such a way that it’s not tedious. Dare I even say . . . fun?

Though I already knew many of the basics that dealt with punctuation and grammar, I bought this book with the intention of honing my editing skills. Sentence structure is something I’m always on the lookout to improve while editing, so I truly enjoyed the chapters that dealt with word-by-word dissection of ad copy, paragraphs, opening lines, and more. I have to admit, I looked at some of those and thought, “Well, that’s not so bad,” and then cringed at how many things had to change to make the clearest sentence possible. As I continued to read, though, the errors became more and more obvious, and I didn’t feel nearly as lacking in my observational skills.

If you’re a writer, you need to read this. Perhaps more than once. It can only help you in making your writing tighter.

If you’re an editor, this little book should be on your reference shelf as one of the handiest guides you’ll ever own. The very end of the book, in fact, is one of my favorite parts: an appendix that lists the most incriminating errors you can make—the ones that will brand you as a hack and tell your readers “the writer is out of her element,” according to Ms. Casagrande. They’re the misused words that drive grammarphiles insane, and the very stuff that will drive an Internet argument off-topic and down the road of personal insults in a heartbeat.

If you’re a homeschooler, you need to get this for yourself and your kids and start them off right, with an instructional book that won’t bore them to tears.

After all, with chapter titles such as “Antique Desk Suitable for Lady with Thick Legs and Large Drawers,” how can you go wrong?
Profile Image for Karolyn Sherwood.
451 reviews34 followers
July 23, 2013
I call myself a writer. I've been at it for over five years. Yet this tiny little book still taught me big lessons. Mainly, I learned to stop using semicolons. I also learned to write short sentences.

No, I'm not trying to be facetious here, this really is a powerful little book. June Casagrande does an excellent job of illustrating her points with both bad and good examples. She walks us through the basics, and shows us how to spot—and how to fix—bad writing. It's easy to think a sentence is a few words followed by a period, question mark, or exclamation point, but we all know there's more to it than that. She explains it all.

This book would be very valuable for any writer who's trying to improve her writing, be it fiction or nonfiction. I highly recommend it.

My only question is: If I stop using semicolons, how will my Reader know I've gone to college?

Five stars.
Profile Image for Lee.
Lee
226 reviews61 followers
January 12, 2014
It was the best of grammar books, it was the worst of grammar books, it was full of wisdom, it was full of silliness, it apologetically introduced complex grammar terminology, it never made much use of all this notation, it concentrated on The Sentence, it concentrated on most aspects of writing since writing is made up of sentences, it had everything to get you started, it had references to get you finished, our writing was going direct to Heaven, our writing was all going direct the other way – in short, the book was so far like every other witty short grammar book, that some of its noisiest authorities insisted on its being received, for good or for evil, in the superlative degree of comparison only.
Profile Image for Johannes.
128 reviews2 followers
December 11, 2018
If you think adverbs are the "best kept secrets" in English grammar and that an appropriate response to semi-colons is to "hate" them -- this book might still be not for you. There is some wisdom here, yes, but I couldn't stand the way too cheery, I'm-your-best-buddy tone. Also, there's a lot of grammar, most of which is tedious and too simple for anybody with experience of languages.

Other than that, it's not too bad, and the chapters are short.
Author  5 books661 followers
January 20, 2013
Yes! YES! I had a gift certificate! I got the latest June Casagrande romp! If you haven't read her, she's a goddess! If you have read her, she's still a goddess -- you just didn't need me to tell you! Don't let the title put you off. Even if you're not a writer, READ THIS BOOK.
Profile Image for Victor *Nothing Happened*.
157 reviews98 followers
March 30, 2017
I made it!

Getting through the last 40 pages felt like I was crawling over broken glass and I still have a pencil in my eye but this is a book that I will have to get a copy of and keep by my desk. I feel so much smarter now and I don't have to use semicolons to prove it.
Profile Image for Filip.
486 reviews51 followers
May 6, 2020
This review originally appeared over at my blog, The Grimoire Reliquary.

It’s rare that you find a book on sentence construction that has so warm a tone. June Casagrande’s It Was the Best of Sentences, It Was the Longest of Titles is an excellent guide on writing, chock-full of common and uncommon issues that plague the amateur and the intermediate writer alike.

“A writer’s guide to crafting killer sentences,” the cover quips at you, and with good reason — why, only yesterday I wrote a sentence so sharp, my fingers are still bleeding. Casagrande offers so much in this tiny 220-page package; her half-amusing hatred of semi-colons alone makes the price of admission well worth it.

What topics can you look forward to reading about? Murderous conjuctions, unparalleled parallels, gerunds to dream nightmares of, and my favourite – short versus long sentences. Plus, appendixes full of well-explained grammar, punctuation and more. It ain’t Tolkien-level extensive but it’s English, not Elvish.

A small complaint – as someone who has studied English for a long time now, plenty of the grammar explanations were at a very basic level. If you’re a grammar noobie, though, this might offer some extra value!

Jokes aside, I learned a lot from this one. Some of the concepts introduced in the chapters, I knew at an intuitive level. Others were familiar. A few surprised me. Either way, I’m glad to have a deeper understanding than I did before, thanks to Casagrande’s approachable book. I’ll be coming back to it time and again. In fact…

I’m planning on writing a blog post for each chapter of the book over the coming weeks – I’ll need something to do come summer!
Profile Image for Shruti Sharma.
184 reviews20 followers
January 1, 2021
Marvelous book. I've read other books on writing, but this one stands apart. The book goes deep into sentence structures. June has addressed every small detail to make sentence writing delightful, both for readers and writers.
Profile Image for Zachary.
304 reviews
January 11, 2023
Nothing earth shattering here, but this book did clear up some misconceptions I used to believe about comma usage and grammar in general. It also contained some great examples on writing for clarity and with the reader in mind. Overall, reading this book has helped me feel more confident in my own writing. Definitely worth getting, even just as a reference.
Profile Image for Melissa Colby.
506 reviews8 followers
March 17, 2017
If you are interested in writing anything from blogs to novels, stop everything and read this now! Casagrande does an amazing job of explaining what makes a sentence well written. It is hard to pinpoint the errors in many people's sentences, but Casagrande makes it easy to understand and entertaining. Her writing is witty and easy to comprehend. After finishing the book, I immediately ordered it off Amazon and downloaded her book on punctuation. I feel like I will need to read this book again to absorb everything in it, but it was worth the time and it will be worth the time to reread it.
Profile Image for Stan James.
224 reviews6 followers
July 21, 2017
This book is like the perfect date for a grammar geek. It's funny, smart, reasonable, and hates semicolons.

June Casagrande does an excellent job of guiding writers through the pitfalls of crafting a sentence, carefully illustrating the many ways one can fumble with just a few words. She offers solid instruction on how to avoid the pitfalls, be on guard for common errors, and generally improve the sentences that form the foundation for all writing, whether it's fiction or non-fiction.

The book ends with some useful appendices, too, though the first one--humbly titled Grammar for Writers--may cause unpleasant flashbacks to English class, depending on the individual. If seeing "Subject + transitive verb + direct object + object complement" gives you the willies, know that Casagrande explains everything carefully, concisely and with a fair amount of humor.

I tend to intuit what works and doesn't work in a sentence without being able to precisely identify a prepositional phrase or a nonfinite clause, so much of this book felt like a remedial course. I don't mean that as a negative, either. It's an excellent guide and Casagrande repeatedly emphasizes that you don't need to memorize every rule (or variation of the same), that you can--and should--break out a dictionary or two when in doubt, and breaking rules is completely okay, provided you actually understand the rules you're breaking.

Overall, this is an excellent and entertaining guide to grammar. I feel like any grammatical goofs I've made in this review will carry extra shame for me, having read this spiffy primer.
Profile Image for Alisa Wilhelm.
1,167 reviews61 followers
November 2, 2020
I read this book for my professional development action of the month. Five stars because it was a good refresher and a fast read, and now I feel better prepared to do my job.

It is full of entertaining examples of bad sentences and how to fix them. I'm good at spotting grammatical errors—that's my job. But I need practice fixing flabby and redundant sentences. This book has practical tips for that and Casagrande walks you through the steps to fix those problems. I'm definitely more aware of common pitfalls and keywords to watch out for. I'd like to recommend this book to some of my clients ;)

Author  0 books1 follower
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July 24, 2017
The author presents the rules of grammar and sentence structure with humor, common sense, and clarifying examples. She follows her own advice by keeping the book short and to the point. It's worth a read, pen in hand, to highlight areas for future reference.
Profile Image for Avi Eisenman.
40 reviews9 followers
March 25, 2019
Very helpful book packed with great information on the various grammatical considerations for creating a sentence. It was a bit dense, and less entertaining than I had hoped for, but I definitely plan on reading it again to get a better handle on all of the grammar rules that I had forgotten.
Profile Image for Daniel B-G.
547 reviews4 followers
November 15, 2018
Decent advice on sentence structuring, though similar to a lot of advice I've read before. Refreshingly short and direct.
Profile Image for Cameron Barham.
213 reviews
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December 27, 2022
“Here’s another way to think of this: Your writing is not about you. It’s about the Reader. Even when it’s quite literally about you—in memoirs, personal essays, first-person accounts—it’s not really about you.”, p. 4
1 review3 followers
February 10, 2015
'It was the best of sentences, it was the worst of sentences: a writer's guide to crafting killer sentences' delivers it promise, to a certain degree. The book certaintly helped me write better sentences, that part of her mission was succesful. But to say I now write killer sentences, not really. I still have a long way to go, but June Casagrande's book proved a solid stepping stone on my way.

The book tries to approach the 'boring' subject of grammer in a conversational style. She speaks to the reader and tries to show how fun grammar can be, with examples of sentences that totally failed and ended up saying something completely different than the author wanted to say.

A few times she went a little overboard with her style and attempts at humor, but overall I quite liked the tone of voice.

The author uses different examples to illustrate why some sentences work and others don't. She explains really well how to improve these latter sentences and often shows multiple ways of 'fixing' a horrendous sentence. So if your sentences suck or they aren't yet as good as you want them, then I'd recommend this book to you. However be warned, the book really is only about sentences. She tells nothing about the flow of multiple sentences, how to build paragraphs out of sentences, etc. I find this a shame, because she only studies the sentences in isolation and a sentence hardly ever stands alone in practice.

Let's be honest, most of us do not write one sentence books, one sentence reviews or one sentence emails. Unless it is to that annoying spammer who won't leave you alone and you tell him to go fuck himself. With her laser focus, only studying the sentence in isolation, Casagrande thus loses the context of a sentence: A sentences stands between other sentences. How do these interact? What makes a combination of sentences a good read? Sadly these questions remained unanswered. I'd really have liked more focus on the sentence out of isolation.

Thank you for your book June. My ability to write clear sentences has improved, but I still have a longer way to go before I write killer sentences.


Profile Image for Joseph Carrabis.
Author  41 books105 followers
February 1, 2021
This is a small, short book that will so heavily impact your writing...no, scratch that.


It was the best of sentences, it was the worst of sentences. is a small book that will impact your writing.


Yes, much better.


If you don't recognize the second sentence is better than the first - you may not understand why it is, but if you recognize it is - this book is a necessity.


If you do understand, you've probably read this book.


I didn't write "...don't recognize that the second sentence..." because It was the best of sentences, it was the worst of sentences. teaches lots about when to use that. I didn't write "...probably already read..." because it also teaches lots about flabby speech and misuse of adverbs.


And how to subordinate for effect, such as "If you..."


And lots more, all with examples.


Casagrande's mantra is "Write for the Reader." Writers who say they write to please themselves first miss the point (almost wrote "are missing the point"); they write for a one-reader audience (rewrote that clause three times). Write to be read. Start with one reader, get more by developing your writing. (a missing conjunction, fix it (she demonstrates how)).


I've written more on my blog.

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