I'm a couple days behind everyone else, but I don't think that will matter too much.
Day #1: Your favorite play
I love starting off with a no-brainer. King Lear, hands down.
I can't tell a lot of the details, they will come out in other answers, but in 1985 I came home from school after reading my first Shakespeare play and announced that I liked Shakespeare. My mother *flew* to the telephone. I think she had the Oregon Shakespeare Festival on speed dial just waiting for the day I was old enough to be interesting.
She had the whole trip planned out, then came down with a horrible case of the shingles. She was better enough to make the drive, but between that and the fact she doesn't do well in hot weather, she was absolutely miserable.
We got to our first play, All's Well That Ends Well, performed outdoors on the big Elizabethan stage...and I *HATED* it. Absolutely hated it. I couldn't follow the plot at all. I could only keep track of one character, and that was because he wore an eye patch. Then, halfway through the damn play, some of his friends pulled some kind of prank to prove he wasn't a brave war hero and HE TOOK THE FUCKING EYE PATCH OFF!!!
At this point, I was done with Shakespeare.
Between the 8 hour drive and all the other plays she bought tickets for us to see, Mom was sweating bullets. First thing the next morning we go to the Tudor Guild bookstore and buy a copy of the Stories of the Plays the Festival puts out every year. It gives a scene-by-scene synopsis of each play, character sketches, some background and history of the plays - pretty much everything that's right up my alley. I poured over it while we ate and I was feeling reasonably secure heading into matinee.
Sure enough, I had good reason to feel that way. The entire first scene, I had a good idea of who everyone was! I kept nudging Mom to tell her who was who (and to keep her awake, she was so sick she really should have just dropped me off, the poor dear).
Then something wonderful happened.
Act 1, scene 2, this guy walked on stage and he was gorgeous. Very Italian, very chiseled, and he commanded everyone's attention. Edmund the Bastard, villain of the play, had every one of us in the palm of his hand as he explained why he was going to be the villain. He hit the lines:
"I grow; I prosper:
Now, gods, stand up for bastards!"
and the audience gave him a standing ovation.
Once again, a standing ovation for the villain in his first scene.
It was all over for me. I was head over heels for the actor, the character, the play, the playwright and the lifestyle.
King Lear is why I am where I am today.
Day #2: Your favorite character
Day #3: Your favorite hero
Day #4: Your favorite heroine
Day #5: Your favorite villain
Day #6: Your favorite villainess
Day #7: Your favorite clown
Day #8: Your favorite comedy
Day #9: Your favorite tragedy
Day #10: Your favorite history
Day #11: Your least favorite play
Day #12: Your favorite scene
Day #13: Your favorite romantic scene
Day #14: Your favorite fight scene
Day #15: The first play you read
Day #16: Your first play you saw
Day #17: Your favorite speech
Day #18: Your favorite dialogue
Day #19: Your favorite movie version of a play
Day #20: Your favorite movie adaptation of a play
Day #21: An overrated play
Day #22: An underrated play
Day #23: A role you've never played but would love to play
Day #24: An actor or actress you would love to see in a particular role
Day #25: Sooner or later, everyone has to choose: Hal or Falstaff?
Day #26: Your favorite couple
Day #27: Your favorite couplet
Day #28: Your favorite joke
Day #29: Your favorite sonnet
Day #30: Your favorite single line