That was a tweet from Matt Yglesias, so here goes:

The best, in order

The Henriad (as a unit!)

King Lear

Hamlet (even if it is a bunch of cliches, strung together)

Measure for Measure

A Midsummer Night’s Dream

Merchant of Venice

As You Like It

Twelfth Night

Winter’s Tale (underrated)

Love’s Labour’s Lost

Anthony and Cleopatra

Othello (slightly overrated)

Richard II + III

Pretty flawed, but I still want to call underrated

Cymbeline

Coriolanus

Troilus and Cressida

OK, and would be pretty awesome from anyone else

Comedy of Errors

Much Ado About Nothing

All’s Well That Ends Well

Overrated, though you still can think they are pretty good

Julius Caesar

Macbeth

Taming of the Shrew

Just not that good

Henry VIII

Two Gentleman of Verona

Merry Wives of Windsor

Timon of Athens

King John

Let’s not even get into the possible co-authorships.

The bottom line

Shakespeare is very likely the deepest thinker the human race has produced, so these are worth careful study! I am a fan of the Folger Library editions.