A Guide to Shakespeare: The 15 Best Plays Ranked

Another year, another ranking! I was going to write a poem SAVAGING Sen. Pat Toomey’s cowardly ass, but that might have to wait until I figure out how exactly I should do that. I’m taking on a somewhat weird project, to try to rank some of Shakespeare’s plays. But I think it will be a useful exercise for those of you wanting to read or see a Shakespeare play, but unsure of where to start. So while I’ll try to keep my descriptions brief, I also hope to give you an idea about the experience of reading each of these plays. Shakespeare can be challenging, but also incredibly rewarding. The language is mind-blowing, the plots are thrilling. If you have the time and patience for close reading and rereading, anyone, regardless of what you typically read, can get a lot out of a Shakespeare play.

1. Hamlet

Kenneth Branagh in Hamlet

The British actor and director Kenneth Branagh holding a skull in his hand in Hamlet. 1996 (Photo by Mondadori Portfolio via Getty Images)

With a gripping plot, brilliant language, haunting imagery, memorable characters, and philosophical investigations that will follow you long after the play’s conclusion, Hamlet has it all. It’s often said that we see ourselves in Hamlet (the character)–that we’re all caught up in this fantastic experiment called life, with no notion of where it’s going or how to make the most of it. So, we try. We try and we try to resolve our relationships, our careers, our talents, our problems–oftentimes we try to the uttermost verge of our hearts and our sanity. The tragedy of Hamlet is that we can try, and still fail.

2. King Lear

Lear is the saddest of the major Shakespearean tragedies (Hamlet, Lear, Othello, Macbeth), occupying a crushingly dark world that allows a constant ray of hope that disappears without conciliation at the conclusion. This persistent chance of a happy ending drags us along, keeping us at the edge of our seats from start to finish. Where Hamlet is closed and interior, within a single family and singular minds, Lear is exterior, dealing with multiple families, where we see the same mistakes repeated and reflected in different circumstances. A challenging play with a complex structure and the breathtaking language of storms and some radical politics on top of it all, Lear is another undeniable paragon of Shakespeare’s brilliance.

3. A Midsummer Night’s Dream

Featuring arguably the most beautiful poetry of any Shakespeare play, A Midsummer Night’s Dream tells a romantic, clever, funny, and wonderfully timeless tale that has been loved generation after generation. Every moment of the play is enjoyable, from the problems of an overbearing father at the beginning, to a petty fight between fairy King and Queen, to the chaos of love potions and couple-swapping, and of course the unforgettable Nick Bottom. A Midsummer Night’s Dream will always be worth a read.

4. The Winter’s Tale

The Winter’s Tale feels in part like a structural exercise, with the first half of the play being a tragedy and the second half a comedy. Sexual jealousy forms the core of the tragic plot, culminating in the shocking demolition of a family, and the infamous stage-direction “Exit pursued by a bear”. But the second half explores redemption with a comic and endearing sensibility, creating an idyllic pastoral setting that, free of the politics and corruption of the city, leads towards a reconciliation that seemed impossible. Yet this fusion of flavors lends The Winter’s Tale a feeling of its own: the feeling of a story that grows and evolves for its own sake. The Winter’s Tale combines Shakespeare’s tragic and comic skills into a single, marvelous work.

5. Twelfth Night


Grown out of Shakespeare’s five years of writing comedies, Twelfth Night weaves together all of Shakespeare’s best comedic elements. A witty fool, drunken idiots, long-lost twins and divided families, a romantic idiot of a man after a woman that’s way better than him, and hardcore gender-bending. Twelfth Night has it all. And it also feels like it has a powerful emotional spine in the story of Viola and Sebastian. Bound to make you laugh, but without foregoing any art or drama along the way, Twelfth Night is Shakespeare’s comedic masterpiece.

6. The Tempest


About an usurped magician-prince living with his daughter and a cannibal on a deserted island revisiting those who betrayed him, The Tempest is Shakespeare’s final play, and really feels like it.  Its poignant poetry, rehashing and redrawing of plots and themes explored over his career, and its captivating use of sorcery (as a symbol for art and writing) create a powerful sense of conclusion. The Tempest is also a fascinating work of literature, as one of first pieces of English literature about the colonial encounter, and due to its relentless and inventive use of symbolism and allegory. The plot in itself is a romantic vignette and a dive into the mind of a master artist. But seen in the context of the rest of his work, this play is important because it concludes Shakespeare’s line of thinking about revenge. Countless plays, from Titus Andronicus to Hamlet, are about revenge, and in The Tempest, Shakespeare at last shows a path to escape from its violent course.

7. Macbeth

The shortest of the tragedies besides Romeo and JulietMacbeth is a whirlwind tour of ambition, murder, and madness. Strangely, despite his reputation of villainy, Macbeth has a strong moral compass, and yet he is still driven to unimaginable acts, which makes a thrilling arc to watch. Combine his arc with a vivid picture of historical Scotland, and the witches with their tumultuous and awesome speeches, and you have an unforgettable play.

8. The Merchant of Venice

The Merchant of Venice is often neglected for its questionable portrayal of the moneylending Jew Shylock. However, this play might be Shakespeare’s most thought-provoking comedy, not for just its look at how society deals with diversity, but also for its strong heroine Portia and a fresh look at relationships and marriage. Shakespeare feels far ahead on issues of gender equality for a late 16th century male poet, and is just as likely to portray idiotic husbands as shrewish wives; The Merchant of Venice is no exception. This is a play exploring the implications of a capitalist, globalist society on our familial and social relationships, flirting with homosexuality and poetry along the way. Its shocking, brutal conclusion also forces us to reconsider how we treat the “Other” in our society.

9. As You Like It

A carefree poetic fantasy, As You Like It is Shakespeare’s ultimate rural play, featuring a merry band of Robin Hood-like woodsmen, a perfect pair of sisters, and the miserable nihilist Jacques. As You Like It does not focus on building to any logical conclusion (the ending is as nonsense as they come), but rather takes a reader on a ride through betrayal, seduction, idyllic pastoralism, philosophy, wrestling, and of course, gender-swapping.

10. Henry IV Part 1


Henry IV is a complex play that is difficult to understand at times for different reasons. Shakespeare’s presentation of the outbreak of rebellion in England in the wake of Henry IV’s seizure of the throne reveals great insight about political authority, English-Welsh relations, the creation of modern politics, and the mechanics of revenge on a national scale. Meanwhile the presentation of the inimitable Falstaff and his world of drinks and tricks thrills with its endless jokes and reminds a reader of a whole other side to the English state, and a darker side to England’s great ‘hero’, Hal/Henry V. The two-sidedness of this play is what makes it enjoyable, balancing epic warfare with tavern jokes.

11. All’s Well That Ends Well

One of the “problem plays”, All’s Well is a comedy that feels way too dark to be a comedy. It presents a world that is irredeemably flawed, characters that are truly corrupt and morally bankrupt, and yet allows the logic of a comedy to take place with witty and sexual banter, coming of age, bed-swapping marriage tricks, and a redemptive ending. Parolles serves as the fast-talking scoundrel that tempts the doofus/stud Bertram to an ill-advised military career; the whole play sits on the backdrop of an aging state with the younger generation unable to compensate for the fading of the older. Familiar tropes are revisited and dissected, as even the wholly impressive heroine Helena has her moments of baffling stupidity. All’s Well That Ends Well is a fun read, but at the end, you’re left wondering why you laughed.

12. Much Ado About Nothing

Much Ado feels like it defines many of the elements that we love about Shakespearean comedies. There’s the unforgettable Dogberry and his malapropisms, the infinitely witty love story of Benedick and Beatrice, a head-over-heels romantic in Claudio, and the wholly unexpected concluding redemption that leaves all involved smiling, celebrating, and married. Much Ado simply doesn’t push beyond these typical elements, but is still a lovable play beginning to end.

13. Romeo and Juliet



Featuring stunning poetry and an insistent exploration of the mechanics of revenge, Romeo and Juliet is a more intelligent play than many would make it out to be. Nevertheless there’s something about it that feels youthful and stupid… Hm… oh wait, I know, it’s the idiocy of not just the title characters, but all the characters. Verona is in a perpetual, pointless urban turf war, old Capulet and Montague wheezing and waving their canes at one another. The tragic ending is as much of the result of mere chance as it is of the ruthless workings of unchecked violence, and while the play is hardly nuanced, the intelligent ideas beneath this unforgettable romance make it an impressive early accomplishment.

14. Measure For Measure

Measure for Measure is a brilliant examination of the city and political authority. How should authority in a city function? What moral standards should its rulers, its citizens be held to? How should a governor engage with the populace? Duke Vincentio asks these questions about his city-state Vienna, disguised as a Friar in order to get a first-hand look. He sees the corruption and deterioration of the city, and yet at every turn makes wrong assessments and questionable judgments in order to have fun at “playing god” in his own city. Featuring bed tricks and head tricks, Measure For Measure poses the strongest critique to the logic of comedies, instead crafting a world that is hauntingly realistic.

15. Antony and Cleopatra

Featuring the most scenes of any Shakespeare play, Antony and Cleopatra is a wild ride through Rome and Egypt, war and peace, and a bizarre love story. Staged more like a fast-paced thriller, Antony and Cleopatra exaggerates as much as it exhilarates. But what holds it together as an excellent play are the title characters- both compellingly torn between beliefs and motivations, and yet in the end, they do love each other. It’s an adult version of Romeo and Juliet– true love, but divided up by political realities and engaging complexity of emotion.


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