Many of us leave school convinced that Shakespeare is difficult, dusty, and not really meant for us. That is a shame, because the truth is the opposite. Understanding Shakespeare is far more achievable than most people expect, and the reward is some of the richest storytelling ever written. This guide offers a warm, patient way in.
Why Shakespeare Still Matters
William Shakespeare wrote more than four hundred years ago, yet his stories keep returning because they are about us. Jealousy, ambition, young love, grief, betrayal, and foolishness have not changed. A teenager falling for the wrong person, a leader undone by pride, a friend who cannot be trusted: these feel current because they are timeless.
He also shaped the language we speak. Phrases such as “break the ice”, “wild goose chase”, and “in a pickle” come from his plays. When you read him, you are not visiting a museum. You are meeting the source of everyday English.
Perhaps most importantly, his plays were written for ordinary crowds, not scholars. The original audiences ate, drank, heckled, and laughed. Shakespeare wanted to entertain, and that generous, popular spirit is still there for anyone willing to look.
The Language Feels Hard at First
Let us be honest about the barrier. The language can feel strange because English has drifted over the centuries, and because Shakespeare wrote much of his work in verse. A few gentle tips dissolve most of the difficulty.
- Read for the whole thought, not the line. Poetry breaks lines for rhythm, but meaning often runs across several lines. Follow the punctuation, especially full stops, rather than pausing at every line end.
- Learn a handful of words. “Thou” and “thee” mean “you”. “Wherefore” means “why”. “Anon” means “soon”. A small vocabulary unlocks a great deal.
- Say it aloud. These are scripts, not novels. Speaking the words, even quietly, makes the sense and the jokes surface.
- Do not chase every word. You will still follow the story even if a few phrases slip past. Trust the momentum.
Read or Watch? Do Both
You do not have to choose between reading and watching. They help each other.
The plays were written to be performed, so seeing them brings out humour, tension, and feeling that are hard to catch on the page. A good production makes the meaning obvious through tone, gesture, and pace. In Singapore, major arts venues such as the Esplanade regularly host theatre, and visiting companies sometimes bring Shakespeare to local stages. Watching a recorded performance at home is an equally valid start.
Reading, meanwhile, lets you slow down, reread a beautiful passage, and sit with the ideas. Editions with modern notes on the facing page are a beginner’s best friend. The table below compares the two approaches so you can pick a starting point.
| Approach | Reading the Text | Watching a Performance |
|---|---|---|
| Best for | Savouring language and detail | Grasping story and emotion quickly |
| Pace | You control it | The production sets it |
| Support | Footnotes explain hard lines | Actors clarify through delivery |
| First-timer tip | Choose an annotated edition | Read a short summary beforehand |
| Ideal use | Deep study and rereading | A warm, enjoyable introduction |
The friendliest strategy is simple: skim a plot summary, watch a production, then dip into the text for the moments that moved you.
A Gentle Map of the Plays
Shakespeare’s works are usually grouped into three families. Knowing them helps you choose what suits your mood.
Tragedies
These follow a great figure toward a downfall, often through a single fatal flaw. They explore ambition, jealousy, and revenge, and they end sombrely. They reward readers who enjoy intense emotion and moral weight.
Comedies
Lighter and playful, the comedies revolve around confusion, disguise, mismatched lovers, and misunderstandings that untangle happily by the end. They are full of wit and are a lovely place to begin if you want to laugh.
Histories
These dramatise England’s past kings and their struggles for power. They blend politics, warfare, and vivid personalities, and they appeal to anyone who enjoys stories of leadership and consequence.
You do not need to read them in any order. Pick the family that appeals, and follow your curiosity.
There are also the sonnets, a collection of short poems separate from the plays. If a full drama feels like too much at first, a single sonnet takes only minutes to read and offers a compact taste of his language and wit. Many readers keep one nearby and return to it, finding something new each time.
How to Choose Your First Play
A kind way to start is to match a play to a feeling. If you want romance and mischief, reach for one of the sunnier comedies. If you crave drama and high stakes, a famous tragedy will grip you. If you love history and power, the history plays await.
Whatever you choose, prepare lightly. Read a one-paragraph summary, note the main characters, and give yourself permission to enjoy rather than analyse. There is no test at the end.
A Few Reassurances
- You are allowed to use help. Summaries, notes, and modern retellings are tools, not cheating.
- Confusion is normal. Even lifelong lovers of the plays reread and puzzle over passages.
- It gets easier fast. After one or two plays, the language stops feeling foreign and starts feeling musical.
Understanding Shakespeare is not a talent you are born with. It is a friendship you build one play at a time. Start small, stay curious, and let yourself be entertained, exactly as his first audiences were. The door has always been open, and you are very welcome to walk through it.
Explore more: Theatre in Singapore: A Guide · Buying Theatre Tickets in Singapore · Local Theatre Companies in Singapore
Frequently Asked Questions
Which Shakespeare play is easiest for a first-time reader? The comedies are a friendly start if you want to laugh, with their disguises and mix-ups that resolve happily. A well-known tragedy suits those who want drama. Whichever you pick, read a one-paragraph summary first and use an annotated edition.
Is it okay to read a modern translation or summary instead of the original text? Yes. Summaries, notes and modern retellings are tools, not cheating. They help you follow the story so you can enjoy the language when you return to it. Many readers use them first, then dip into the original for the passages that moved them.
Why does Shakespeare use words like thou and wherefore? Those words were ordinary in his time. Thou and thee mean you, and wherefore means why. English has drifted since, so they look strange now. Learning a small handful unlocks a great deal, and the rest becomes clearer once you read aloud.
Should students watch the play before studying it for school? Watching first often helps, because the plays were written to be performed and a good production clarifies tone and humour. Then read the text for the scenes you need. Check with your teacher about which edition or version your syllabus expects.
Are Shakespeare’s sonnets easier to start with than the plays? They can be, since a single sonnet takes only minutes to read and gives a compact taste of his wit and language. Plays reward you with story and performance, so many readers enjoy dipping into both rather than choosing one.
Further reading: Shakespeare in the Park Singapore: What to Bring and Expect