From my friend:
Othello is good, probably one of the easier tragedies. The easiest tragedy would probably be Romeo and Juliet. Easiest comedy would probably be Twelfth Night or Taming of the Shrew. Hamlet, however complex, has the advantage of having a full, unedited film version (w/ Kenneth Branagh).
My recommendation is to find an UNABRIDGED "book-on-tape" version of the play (iTunes is good for that), and read along with it. I do that when I have to teach a Shakespeare play, and I find it very, very helpful (I can pause and make notes in the margins, and it's so much easier to understand monologues when hearing them too).
Also, look at the No Fear Shakespeare series online (
http://nfs.shakespeare.com/). NFS has the Shakespeare on the left, and a "modern translation" on the right. It's a legit way of understanding it - I use this with actors all the time.
For a pre-1900 play, I would look at something Anton Chekhov wrote before 1900 (he's Realism, so easier to understand). There's also Racine's "Phedre," and Edmond Rostand's "Cyrano de Bergrerac" (there's a great film version with Gérard Depardieu).
Hope this helps!
[URL="http://nfs.shakespeare.com/"]http://nfs.shakespeare.com/[/URL]
nfs.shakespeare.com
Oh, and Cyrano de Bergerac and almost all of Chekhov's works can be found online. Good luck!
Hope this helps.
