William Shakespeare wrote his first play over 430 years ago, and yet we still consider his work to be some of the greatest writing in the English language. Shakesepare’s plays are beloved for a reason, they truly are masterworks.

We are firm believers that everyone should experience the passion and fantasy of his plays, but it can be intimidating to dive into the work of this literary legend. Elizabethan English isn’t the easiest to understand, and his iconic mastery of language can sometimes make it seem like even more of a puzzle. If that weren’t enough, how does one choose which of his 37 masterpieces to start with?

Fear not, we’ve got you covered! We’ve chosen these five plays because they are easy to follow, frequently performed, and they happen to be some of Shakespeare’s most famous works.

Romeo & Juliet

Written between 1591 and 1596

It’s Shakespeare’s most iconic love story
It’s a classic

”Parting is such sweet sorrow.” Whether you’ve seen the play, the movie, the ballet, the opera, the poem, the painting, we could go on… chances are you know the plot of his one already, which makes it a great place to start if you’re new to Shakespeare.

We’re not ashamed to admit that Elizabethan English can be tricky to understand. With backward phrases and outdated references, it can take a minute for your ear to get used to it. Watching or reading a play with a storyline you’re familiar with is a great way to get a feel for Shakespeare’s famous iambic pentameter, or the rhythmic structure of the lines. Context clues and pop culture references will help you decipher Shakespeare’s clever story like a pro. Plus, the romantic storyline is a classic for a reason.

This production from Shakespeare’s Globe is everything you imagine when you think about this famous love story. This classic production also happened to be Game of Thrones star Ellie Kendrick’s stage debut at just 18 years old.

Julius Caesar

Written in 1599

Short and not so sweet
Based on History

”Beware the ides of March!” Julius Caesar is another great option for your first Shakespeare play.

For starters, you may already be familiar with the story of the tyrannical Roman Emperor whose rule led to the fall of the Roman Republic, which will make the plot easier to follow. Thank you Ancient History 101.

This play is also one of Shakespeare’s shorter plays. Although not the shortest on this list, most people have no trouble getting through it in a little over an hour. Even though it’s about an Emperor who ruled in 44 BC, the story is timeless in the themes that it explores like ethics and politics, fate and free will, good and evil, and tyranny and honor. Plus, if you need any help deciphering Shakespeare’s riddles there are plenty of school guides floating around that will make you an expert in no time.

This production from The Royal Shakespeare Company stars Andrew Woodall as the doomed emperor, and James Corrigan (This England, This is Going to Hurt) as his nemesis Mark Antony.

Much Ado About Nothing

Written in 1599

The Original Rom-Com
Filled with hilarious insults you’ll want to steal

”When I said I would die a bachelor, I did not think I should live till I were married.” Much Ado About Nothing, sometimes called Love’s Labour’s Won, is a great example of Shakespeare’s masterful humor.

The story follows the famous bachelor Benedick, who vows never to marry, and the independent Beatrice who vows never to become a bride, but wait, are they perfect for each other? Their friends think so, and devise a clever plot to help them realize it.

Did someone say Rom-Com? Full of sharp wit and liquid banter, this play is always a joy to read and watch, you may even pick up some new Shakespearean insults along the way.

This production from The Royal Shakespeare Company is a piece of cake to understand thanks to Shakespeare master, and Olivier Award Winner, Michelle Terry’s acting chops.

Macbeth

Written 1606

Shakespeare’s shortest tragedy
Has all the thrill and drama of a modern psychological thriller

”Something wicked this way comes.” This is one of Shakespeare’s most famous tragedies for a reason. Often referred to as ”The Scottish Play” many people consider this tragedy to be easier to understand than Shakespeare’s other celebrated tragedy Hamlet, which makes it a good place to start if you’re looking for a good tragedy to sink your teeth into.

The basic story is about the Scottish general, Macbeth, who is told by three witches that he will be the future king of Scotland, but what must he and his power-hungry wife do to fulfill this prophecy? We’ll give you a hint, it starts with ‘M’ and rhymes with ‘herder’. Ultimately, it’s a classic story of good and evil that will keep you on the edge of your seat. Just be sure not to say the name ”Macbeth” in a theater or you’ll be cursed with bad luck.

This production from The Royal Shakespeare Company is dark, exciting, and wonderfully acted. This production also marked Christopher Ecclestone’s (Doctor Who) RSC debut.

Twelfth Night

Written in 1601

A riotous comedy of mistaken identity and unrequited love
An absolute matrix of love triangles

”If music be the food of love, play on.” Twelfth Night is probably one of Shakespeare’s most beloved comedies. This might be, in part, because the plot makes a lot more sense than some of his other wild plays.

Viola and her twin brother are in a shipwreck, she thinks he’s dead, and he thinks she’s dead. She pretends to be him and goes to work in the house of an aristocratic woman, Olivia, who falls in love with Viola ( now called Cesario), but Viola is in love with the Duke, and the Duke is in love with Olivia. Ok so maybe it’s a bit more complicated than we let on, but once you’ve sorted out Shakespeare’s complicated love triangles, Twelfth Night is a breeze. Ultimately, it’s a classic story of mistaken identities that’s both tragic and hilarious, and it’s the kind of show you’ll enjoy regardless of how much Elizabethan English you know.

This production from The Royal Shakespeare Company is set in the late Victorian Period and features a stunning set that feels like a movie.

No matter which Shakespeare play you choose as your first, you’re in for a whirlwind of entertainment. Want to test the waters before your trip to the theater? You can watch full productions of Shakespeare’s plays on Marquee TV in our Shakespeare Collection.