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My absolute favorite play is Hamlet. I haven't read it for 15 years, but I can still quote it - it really stuck with me.

Hamlet is both the longest and the most linguistically difficult of all of them so it might not be the best place to start.

Of the tragedies Julius Caesar is the shortest and most accessible one when it comes to readability.

The histories usually feature a great number of characters and it's not easy to keep track of all of them, not to mention their interconnectedness.

Generally, the popular comedies are quite readable and to the point so maybe you could check their summaries and see which one appeals to you the most.

I think Othello is quite accessible, and so is Hamlet. King Lear would be a next choice, while I'd leave Macbeth for later.

My best advice would be to get your hands on a serious edition, providing detailed notes. Arden is the go-to choice for most scholars.

To me As you like it is one of the best plays to start with
As You Like It

I agree with finding an edition with detailed notes. I think 'As You Like it' is wonderful and funny, whilst 'Romeo and Juliet' is very accessible, followed by 'Hamlet' and 'Macbeth' (these last two follow similar thematic concerns).

I agree with Chris, that Hamlet can be a difficult and tedious read when you're not familiar with Shakespeare's verse. I do suggest you should try it once you feel comfortable with the dialect and writing style though, as many of the soliloquies are incredibly beautiful and relevant to the human experience.

For reading your first Shakespeare play, I think it comes down to your personal preference. I think Julius Caesar is a good play when you enjoy history. It's based on the rise and fall of Julius Caesar, but is also is to a certain degree a fictional recreation of it that is really interesting.

If you enjoy comedies, you may start with Twelfth Night or Midsummer Night's Dream. Twelfth Night is more commonly parodied in modern life, but I think Midsummer Night's Dream is more accessible if you have no prior knowledge of Shakespeare. It's what I started with, and is never supposed to be taken to seriously. Most of the verse is easier to understand, or meant to make the language more beautiful rather than to give crucial plot information.

If you do prefer to read a drama, Romeo and Juliet is a safe place to start. However, If you are feeling ambitious, Macbeth may be a more interesting one to start with. I think both are accessible. Everyone knows the story of Romeo and Juliet, so that makes it easier to follow. Macbeth is a much grittier and psychological, which in my opinion makes it more interesting. If you are interested in Hamlet, I would read Macbeth first to get a sense of what kind of drama you would be preparing for.

There are tons of Shakespeare companion guides that will assist you with the language as you read. No Fear Shakespeare is the obvious one that changes the entire script to be modern, and also includes definitions for some of the more difficult wordings. You can access it online and it's very convenient to follow along with. If you want a hard copy to read from, I'd suggest finding a Folger edition for whichever play you want to read. It has the show on the right pages, and definitions for that page on the left.

I hope this helps you get involved in Shakespeare!

The Merchant of Venice is easy Shakespeare reading and a very enjoyable play.