Looking back at my high school English classes, it's kind of funny how we all got introduced to Shakespeare with the same handful of plays. The ones that have really stuck in the public mind—and on classroom syllabi—are the major tragedies. 'Hamlet' is probably the peak. It’s got that indecisive prince, the ghost, the existential ‘to be or not to be’—it’s the one that everyone seems to reference even if they’ve never read it. 'Macbeth' is another big one, a much tighter story about ambition and guilt. 'Romeo and Juliet' is the tragedy everyone knows first, though I’d argue it’s more famous as a cultural idea of doomed romance than for its actual text.
Then you’ve got the comedies and histories that have their own fame. 'A Midsummer Night’s Dream' is everywhere, from school plays to ballets. Its mix of lovers, fairies, and a donkey-headed weaver makes it super accessible. The histories are dominated by 'Henry V', especially the St. Crispin’s Day speech. But honestly, I think his fame rests most solidly on that tragic quartet: Hamlet, Macbeth, Othello, and King Lear. 'King Lear' is less of a pop culture staple than the others, but among people who actually study literature, it’s often considered his absolute masterpiece. The others are more famous for their iconic characters and moments.
It’s also worth mentioning the sonnets. They might not be ‘books’ in the play format, but Sonnet 18 (‘Shall I compare thee to a summer’s day?’) is arguably one of the most famous poems in the English language. So when people list his famous works, the sonnets belong in the conversation for their massive cultural footprint, even if the plays get top billing.