Shakespeare is said to be the greatest poet-dramatist of all time. His plays have a range and quality to them which have been unmatched since his time.
One reason I find his work fascinating is seeing how the English language has evolved since his time. Apart from the changes in spellings (which were not standardized back then), some of the words and phrases also have retained the same spelling, but changed in meaning. For example, “silly” originally meant happy and blessed.
The other interesting reason is how he masterfully weaves his sentences and words together to produce a rich depth of meaning.
For example, in All’s Well That Ends Well, the Countess of Rosillion describes Helen, who she has been taking care of after the passing of the latter’s father, below. She proclaims that Helen has every right to love who she desires :
Faith, I do: her father bequeathed her to me; and
she herself, without other advantage, may lawfully
make title to as much love as she finds: there is
more owing her than is paid; and more shall be paid
her than she’ll demand.
In the above, Shakespeare gracefully interleaves the meanings of economics and love.
On the subject of classical works as a whole, I think there is a treasure trove of literature in some of the classic Kannada and Sanskrit works. It is interesting to read such texts from the source and discover their nuanced meanings.