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25 Great Sentences and How They Got That Way

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Virginia Woolf, Toni Morrison, Neil Armstrong, Jack Kerouac, Yoda: these are just a handful of the writers and speakers whose words are parsed in this diverting romp through sentences culled from poems, essays, speeches, songs, fiction and film.


In chapters titled for distinctive features, such as “U-turn” and “impossibility,” master teacher Geraldine Woods deftly reveals the underlying craft that goes into the creation of a memorable sentence. Literature lovers will be delighted to discover new authors and revisit favorite passages from a fresh perspective. And writers who want to stretch their skills by following the prompts in each chapter may well find themselves feeling as Henry James did when he wrote, “I have many irons on the fire, and am bursting with writableness.”


This is a must-read book for any resister of grammar-bound, sentence-diagramming analysis who wants to understand the art that lifts a sentence from good to great.



256 pages, Hardcover

Published August 18, 2020

84 people are currently reading
475 people want to read

About the author

Geraldine Woods

89 books25 followers
Geraldine Woods has taught English at every level from fifth grade through Advanced Placement, most recently at the Horace Mann School. She is the author of numerous nonfiction books for adults and children, including 25 Great Sentences and How They Got That Way. She lives in New York City.

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5 stars
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54 (34%)
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45 (29%)
2 stars
14 (9%)
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Displaying 1 - 30 of 35 reviews
Profile Image for Sirah.
3,048 reviews27 followers
September 12, 2025
It would be easy to confuse this book for a collection of categories. But that's not quite what it is. Each of the 25 chapters starts with a sentence that does a particularly good job showcasing a writing technique, such as repetition or the use of multiple verb tenses. The author explains the context of the sentence and waxes on enthusiastically about some of the hidden ways the sentence interacts with itself and with the rest of the piece whence it came. Other examples of each technique are then paraded in front of the reader, followed by some writing prompts/challenges to see if you can use the technique yourself.

This book is quite the deep dive into some pretty subtle techniques. The first few chapters confused me (I'm still not sure quite what constitutes a pocket sentence), but I appreciated getting to see the author analyze each sentence from a variety of angles. Since I do a lot of literary analysis, I found this example quite useful. Did this book inspire me to read any of the books/written pieces mentioned? No. Did it inspire me to write using any of these techniques? Not specifically. However, I am walking away with some new ways of thinking about sentence construction and the value of both knowing the rules and understanding what the effects might be if the rules are bent or twisted a bit. I wouldn't call this book a must-read, but if you get as deep in the weeds with your literary analysis as I do, you'll likely find this book a valuable resource.
74 reviews2 followers
Read
March 29, 2021
Fascinating for writers. How these great pieces developed. Genius at work.
Profile Image for Jimmy.
Author 6 books283 followers
April 16, 2021
Here is a list of the different kinds. You will have to read the book to see the actual 25 sentences and learn how they grew.

Part I: STRUCTURE
1. Pocket
2. Crossed Sentence
3. Parallelism
4. Reversed Sentences
5. Surprise
6. Questions

Part II: DICTION
7. Valuable Verbs
8. Tone
9. Word Shifts
10. Coinage

Part III: SOUND
11. Onomatopoeia
12. Matching Sounds
13. Repetition

Part IV: CONNECTION AND COMPARISON
14. First Person
15. Second Person
16. Contrast
17. Negativity
18. Creative Descriptions
19. Synesthesia

Part V: EXTREMES
20. Marathon Sentences
21. Simplicity
22. Contradiction
23. Time
24. Impossibility
25. Visual Presentation
Profile Image for Sandra Groom.
Author 2 books1 follower
December 31, 2020
Books about the craft of writing typically fall into two camps; those which focus on the detail and technical aspects of writing, such as punctuation, point-of-view, or narrative; and those which take a more meta-view, such as inspiration, creating a distinctive voice, or story structure.

25 Great Sentences and How They Got That Way appears at first to fall into the first camp. Its very title tells you that author and English professor Geraldine Woods is concerned with what she considers the building block of any writing (fiction, non-fiction, prose or poetry), the sentence. But I soon discovered that this book also encourages readers to think about the 'why' as well as the 'how'. What are you trying to achieve with your writing, and how might carefully crafted sentences help you achieve it?

In each of the 25 chapters she highlights a sentence exemplifying the point she wishes to make, for example repetition, cross-over, exaggeration, onomatopoeia, etc. Each chapter ends with a series of exercises for the writer to practice the new-found skill.

As a writer, I found this book the perfect combination of inspiration and instruction. It encouraged me to experiment with word order, with word choice, with punctuation even. While I recognised many of the examples given in the book as beautiful, or compelling, or memorable sentences, Geraldine Woods explores what makes them this way, and how you can apply similar techniques to your own writing.

For anyone who wants to improve their writing, or enhance their reading pleasure, I highly recommend this book.
9 reviews
April 7, 2021
Had mixed feelings about this book. On one hand, Geraldine Woods collected examples from a wide variety of genres and provided interesting vignettes about the authors, the works, and the circumstances in which the chosen sentences were crafted. It introduced me to authors I would not otherwise come across and heightened my appreciation for the writing craft.

On the other hand, I did not feel like I really learned anything new or useful/applicable. The first few chapters reminded me of a Music Theory class I took in college: we learned to reduce complex works (sonata or symphony movements) to a progression of few notes, and while I could see the logic and learn the technique for how to do it, I was mystified by its purpose. I am certain that Beethoven did not start with a five-tone reduction and then developed it into Eroica. Just as I am certain that Virginia Wolf did not say, Let's use a pocket sentence here, and thus started "Mrs. Dalloway."

One example provided a true revelation. Wood unpacked a masterful sentence from Jane Austen's "Northanger Abbey," it took three pages to explain three short lines, and the depth of its meaning took my breath away. Some other expositions, though, seemed to read into the text more than what was there.

The "For the writer" exercises at the end of each chapter were designed to "improve your ability to write," as she says in the Introduction, and I suppose they can be helpful in that.
Profile Image for Cheryl.
13k reviews484 followers
September 27, 2025
I've no desire to be an author, but I'm going to do a few of these exercises anyway. Most, however, are aimed more at students or writing groups, it seems. The main text is more interesting, but I'm not sure how well I'll be able to take that which I'm learning here to texts that I read in the future. That is to say, when I come across something that seems especially well-written, will I be able to say, 'oh yes, that was an excellent use of a pocket sentence' or 'second-person was indeed the most effective voice for this story' or whatever? I doubt it.

No, mostly I'm here for the samples of great writing. And yes, I am being introduced to authors and works I didn't know before. Not a lot, but enough. Overall the book is worth reading, or at least browsing through, imo.

Bad Mouth: Fugitive Papers on the Dark Side by Robert M. Adams has the sentence "History does not unfold: it piles up." Good thought. Woods includes this in a chapter she calls "Contrast." I question the use of the colon... but I can see why it might be more effective, at least for some readers, than a semi-colon. (Apparently I'm too fond of semi-colons, according to some.)

Zora Neale Hurston has a great sentence in the Contrast chapter, too: " I do not weep at the world - I am too busy sharpening my oyster knife."

The song *Amazing Grace* was written in 1779 by "John Newton, a slave trader who became an abolitionist and cleric."
"I once was lost, but now I'm found / 'Twas blind but now I see."
(What a wonderful thing to learn, that someone can reform himself like that!)

I'm glad to learn other things, too. For example FDR's 'fear itself' exhortation was about the Great Depression, not WWII as I always assumed.

Ronald Reagan said "How can we love our country, and not also love our countrymen?" So, Reagan would be considered a moderate nowadays?

Edna St Vincent Millay wrote "I like humanity, but I loathe persons." That's backwards for most people isn't it?

Anyway, pretty good book in my personal opinion. You might love it, or think it a waste of time... but if you're interested, I do hope your library has it so you can see for yourself.
Profile Image for Solomon.
13 reviews
April 16, 2024
A delightful book. A good author sharing her passion.

So many writing books are really more about editing than the act of creation itself. That's where this one stands out. Each great sentence--and the myriad examples that follow--models a different way you can communicate your ideas to the world. Tired of being told that a sentence is subject-predicate-period, Woods set out to show all of the other structures, sounds, and techniques that can create a "unit of discourse."

Her great sentences come from just about everywhere--British classics are frequent sources, but so are Yoda, "The Little Engine that Could", and Hamilton (the musical). Some sentences excited me more than others, and some chapters were better than others. The whole structure section was fantastic, for example, but her treatment of tone and verb choice were more cursory. And I often felt that certain authors were snubbed (the chapter on coining words skipped both Tolkein and Orwell???). But that's not the point. The point is she got me thinking about all of the other places I'd seen these techniques used before, and how they improved the writing, and how I could use them in the future.

I picked up this book looking to grease my mental wheels after not writing for awhile, and that's exactly what it did. I even found myself doing most of the short writing exercises she suggests. Her passion is contagious. It's clear she could hardly contain her excitement as she piled more and more examples into each chapter, like a living room cluttered with stacks of books that could never fit on the shelves. Count me among the inspired.
Profile Image for Kristin Boldon.
1,175 reviews45 followers
March 2, 2023
The author loves writing and has many examples of sentences from a variety of venues, not just literature, to illustrate her examples of things like Time, Impossibility, Contradiction, etc. The sheer delight of the range of sentences could be fun, but could also be tiring, like she was using up her index cards of example sentences. I feel like this would've made a good, shorter book with more carefully curated choices. She includes writing prompts, and they seemed fine but I didn't use them. In the end, despite some good analysis and a smile at one of two particular sentences, this felt like being lectured to by an English teacher, and one who had a grey-haired sense of humor. Not one for the keeper shelf.
Profile Image for Jennifer Holmes.
579 reviews20 followers
January 16, 2026
An easy-to-read, under-the-radar book for writers and readers who want to think more about the literary devices that take a sentence from good to great. A short course in how to read more critically.
Profile Image for Eileen.
58 reviews4 followers
February 2, 2021
A very good book if you are a writer, thinking of being a writer, or learning, or learning to help others write.

This book should be read a second time for implementing the ideas into words.
79 reviews
November 21, 2022
Very insightful book that prompted me to think about stories on a sentence-by-sentence and word-by-word level. Has some interesting writing exercises too!
Profile Image for Tandava Graham.
Author 1 book64 followers
October 24, 2020
My personal collection of “great sentences” is geared more towards sentences that stand alone as being impressive, beautiful, clever, etc. in their own right, even out of context, like poetry in miniature. From that perspective, Woods’ “great sentences” weren’t all winners, and often tended to be more just illustrating a technique, or being effective in context. But what I liked was that the 25 sentences referred to by the title were just the first examples, one per chapter, and they were followed by many others in each category, from books, poetry, songs, and other sources—Monty Python even made a cameo with a line from the Dead Parrot sketch. The format was very good: each chapter starts with a detailed examination of the leading sentence and the concept it embodies. Then we get lots of other examples, with less commentary. And finally, there’s a section “for writers,” which offers some ideas and inspiration for writing your own sentences with the same qualities. You might not want to bother with these exercises (I read them, but didn’t actually do them myself), but they could be useful for teachers, for example.
Profile Image for Miles Jaffee.
27 reviews
January 12, 2025
An exciting new way to tell you all about exactly what you already know subconsciously.
Had its occasional good bits, but so English-teachery.
Exercises were very paint-by-numbers, I feel like the only real exercise for most of the sentence types would just be "write a story that uses a bunch of these."
Condescends to include "low art" like tv and song lyrics in addition to poetry and literature, but only looks at the most surface-level stuff, not the actual great lines that can be found there if you know where to look. Like, they brought up Bob Dylan's mediocre, tossed-off "Lay Lady Lay" in the section on alliteration, but had none of the poetic surrealism that made him the only songwriter ever to win a Nobel prize, even when there were two lengthy sections on surrealism/contradiction... ditto with Orwell being in that contradiction section for "strength is weakness" but gettinh snubbed in the chapter on coining words when coining words was an academic field of research for him.
Good read before bed though, got me in that peaceful sleepy unstimulated mood.
Profile Image for Margaret Perkins.
261 reviews1 follower
February 21, 2023
Finally done! I bought this at a little indie bookstore and thought it looked perfect for me - a book analyzing great sentences from literature and teaching me how to write killer sentences of my own? But in actuality it wasn't as good as it sounded. It gets a solid three stars for the sheer number of writing exercises; I did try several and they were pretty fun and helpful. But I wasn't happy with most of the sentences featured, and the whole thing turned into a bunch of chapters on types of sentences rather than true close reading of noteworthy, literary sentences (if that makes any sense). The beginning chapters were more interesting to me but I really didn't gain many new insights from it overall. It's still a valuable book, but maybe a little young for me.
Profile Image for Agnes.
713 reviews2 followers
July 27, 2023
What's with Cocaine, Geraldine?

There! I got your attention!
I liked this book so much I checked out the author on Good Reads, she has read only 1 book- "Cocaine", which she wrote, but she gave it 1 star???!!!! That's odd!

Anyway, I enjoyed this book- there was diversity in the media chosen and she gave writing exercises with every chapter which I think should have been noted in the title. She is super smart and good at dissecting & explaining things.

I particularly liked- "Are you there God? It's me, Margaret." MLK's "Letter from a Birmingham Jail" and the passage from "Catcher in the Rye."
Profile Image for Audra Neagle.
256 reviews2 followers
May 26, 2024
I bought this because I wanted to to use it in my AP Lang classroom. I tuned out a bit as I was going through it because it started to actually feel like work.

I think I expected this to be a deep-dive into 25 well-known sentences in literature, and while there were some of those in the book, there are many, many sentences that exemplify the 25 composition rules that Woods highlights. This is more about sentence CONSTRUCTION and how syntax creates meaning than it is about breaking down literary symbolism within sentences.

It’s definitely on target with AP Lang, and I was able to use some of Woods’ writing exercises for my classroom. I would not recommend it unless you’re interested in writing as a craft.
Profile Image for Sarah Kelsey.
465 reviews17 followers
December 25, 2021
A good text, worth reading.

Essentially she covers some of the syntax I teach my high school students (anaphora, chiasmus, parallelism...) along with other elements like patterns of sound and figurative language. Each chapter provides several variations of the chapter's focus, each taken from well known authors, and provides analysis and explanation of the effect of each example. Each chapter ends with writing exercises to promote play with the techniques.
Profile Image for Jeff Duda.
50 reviews
June 12, 2023
There are many more than just 25 examples of sentences good authors use in here. Probably more like 500. In my opinion (whatever that is worth) some of thesentences don't work well (i.e., don't seem all that "great") without context. But many do. The chapters all end with myriad exercises for the reader.

Overall, a great tool for an aspiring writer or someone who is looking for some inspiration and a nudge out from behind that writer's block.
Profile Image for Lindsay Smith-Munoz.
161 reviews
Read
June 16, 2021
It was well researched, and it provided so many examples of great sentences, along with thoughtful analysis of what makes them great. It was interesting both as an approach to literature and as an approach to writing. I found that last 1/3 of the book had some ideas that were a bit repetitive with the first 2/3, but not so much that I couldn't enjoy it right to the end.
Profile Image for Mathieu.
197 reviews
April 16, 2025
A really enjoyable read for anyone who enjoys reading. Learned authors welcome, but not just for learned authors! More than 25 sentences presented in 25 chapters in 5 sections to expand your enjoyment, skills, understanding, and breath of approach that many great authors have used to express themselves and aim the thoughts of readers. Fun!
82 reviews1 follower
January 21, 2022
I use 1 star ratings to designate a DNF. Got from the library but didn’t expect to have all of the writing exercises. I may buy this book so I don’t have a time constraint then update my rating and review.
44 reviews
February 16, 2022
It's probably a four star book, but a three star review because I didn't read it correctly. Had I followed the prompts and learned with the book, I'm sure I'd bump it up. But library due dates being what they are, this book was read, mostly enjoyed and gone again.
150 reviews1 follower
July 10, 2022
I’m not a writer and so was surprised but amused by the writing exercises at the end of each identified sentence style. I do hope I can be more cognizant of an author’s emphasis as expressed based on sentence structure.
Profile Image for Emily Fairchild.
31 reviews
February 1, 2024
Overall I thought this book was great for writers and non-writers alike! The writing exercises were very approachable and I appreciated the diversity of featured work (from Mindy Kaling to Shakespeare) in the examples for each chapter.
1 review
February 24, 2021
Good

I found this fun to read! It would be a good source for people wanting to try different writing styles.
Profile Image for Joanna.
765 reviews10 followers
November 17, 2021
An excellent exploration of what makes writing stand out, along with exercises for writers to explore how to use such construction in their own works.
Profile Image for Stephanie G. Lewis.
570 reviews
May 1, 2022
Not what I expected. Not interested at the mechanics...I was looking for magic. It was lost soon after the introduction.
Displaying 1 - 30 of 35 reviews

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