Whatever you go with, always read Shakespeare out loud. That is how you can feel the contribution to English through the prosody of his writing.

It's hard to really recommend what you should read first, since I don't know you. But when I was in high school we read Romeo and Juliet first. Hamlet is pretty great for very young people too, as Hamlet is like 17.

I found Richard III more interesting than Macbeth, personally. Macbeth has more spooky stuff and the theme of guilt whereas Richard III has a lot more to do with interpersonal drama. I'm just going to free-flow ramble about the different ways these particular plays could be connected (and so a sort-of suggestion of how to read them). Always read Shakespeare out loud. You could easily get bored or confused with the text otherwise, and like I said, you start reading out loud like an actor, you'll understand why he's still so celebrated today.

Othello - Hamlet - Macbeth - Richard III : a cycle on tragedy, villainy, choice, hate. Read these in any order; my order has to do with a weird hero vs villain virtue math that I'm still debating with myself over.

Romeo and Juliet - Antony and Cleopatra : there are enough parallels to enjoy these two together

Julius Caesar - Antony and Cleopatra : IMO Marc Antony may have been one of Shakespeare's favorite heroes from ancient times and you see a lot of him in these.

Much Ado About Nothing - A Midsummer Night's Dream : comedies more to do with frivolity, antics, and folly - as opposed to idiocy or lunacy (Shrew)

The Taming of the Shrew : I read this recently, this is a rather standalone play as its comedic literary conventions are (and were historically) rather rough if you forget the induction. I would read the Wikipedia page about this ("Analysis and Criticism" - "Themes") afterword to complement it.

I would pick up a copy of Twelfth Night or even Two Gentlemen of Verona before you read The Taming of the Shrew to get a better idea of Shakespeare's "typical" comedies...Shrew does not have a true "center of good" character IMO, which makes it one of the more challenging of Shakespeare's plays to reconcile with (especially as a comedy): everyone sucks and you are left wondering wtf sort of world is this. The framing technique Shakespeare uses at the start of the play is essential to understanding "the joke" but for a lot of people historically, it is not enough and the play can leave the audience a bit uncomfortable. The movie 10 Things I Hate About You is an adaptation that really brings together the story and modernizes it in a way that is hyper-palatable and lovable.

Everyone has given great suggestions. I echo the sentiment, "it doesn't really matter, just dive in." Your curiosity and reverence for the work will be the only equipment you'll need. I think very fondly of the time I took a college course on Shakespeare. Something that really enriched the experience was to watch an adaptation film as soon as I'd finished reading.

Macbeth. Plenty of intrigue and weird goings on to keep your interest. Watch Roman Polanski's film for a real treat.

Look I would recommend reading them all one by one.

I did it when I was in college. They are all full of knowledge.

If I can go by my personal choices, I would rank tragedies first. The second choice would be to read the comedies. And lastly read tragi-comedy.

Hamlet is my favourite and Romeo and Juliet is just second, the third I can rank is Macbeth and fourth is Julius Caesar.

God, my favorites change constantly, but Hamlet, Macbeth, Romeo and Juliet, Richard III, Antony and Cleopatra, Twelfth Night, and Much Ado About Nothing all strike me as good entry points.

But also, reading Shakespeare is great, but watching it is even better. If there are local performances, try to see some. Twelfth Night is one of the ones I think gets performed the most around here, and is a great first Shakespeare for a lot of folks. The Kenneth Branagh films of Henry V and Much Ado About Nothing are also a blast (and the contemporary Joss Whedon take on Much Ado is surprisingly fun, too).

Then start enjoying how the plays get interpreted and reinterpreted. There are modern takes, sci-fi ones (Forbidden Planet is a twist on The Tempest), etc. There's a fantastically funny tv show called Slings and Arrows about a theatre company in Canada, with the seasons devoted to productions of Hamlet, Macbeth, and Lear, that I just love (but it works best once you know the shows).

In terms of tragedies, Macbeth, Romeo and Juliet, or Hamlet are probably easiest. Macbeth is the shortest tragedy. It moves pretty quickly, and is the most like an action movie of the options. There aren’t very many slow or confusing scenes, although there are 1 or 2 that drag on a little bit. Other than a few moments, it’s generally pretty easy to follow.

(For filmed versions, I really like the National Theater Macbeth, the Baz Luhrmann Romeo + Juliet. I don’t love the Kenneth Brannagh Hamlet, but it’s a good starting place. If that’s not your thing, David Tennant’s Hamlet is also pretty good)

Romeo and Juliet is little longer and more complicated, but most people are familiar with the plot. It’s an interesting play, and it’s cool to draw your own conclusions about such a popular and frequently misrepresented story.

Hamlet is definitely very long, and has some very confusing moments. However, it’s one of the few plays that doesn’t have simultaneous plots. The play is about Hamlet, and every scene either contains him or is about him. One of the hardest parts of Shakespeare is keeping track of countless characters and plotlines, and Hamlet is free of that. It’s also just a really good play.

In terms of comedies, I’d recommend Twelfth Night or Much Ado About Nothing. Both plays have some complicated moments, but neither is overly long. They’re fantastically well written, and have some humor that’s still pretty funny today.

(for filmed versions, the Twelfth Night movie with Helena Bonham Carter and the Much Ado production with David Tennant are pretty good)

That being said, there really isn’t a wrong play to start with. The key is to choose one that interests you, and take your time. I always recommend reading a summary first— you don’t really lose any of the magic by having a few spoilers, and it makes it easier to follow the action when you know basically what’s happening. I also really like using the Sparknotes modern English translations. If you read them online, they’ll give you a side by side comparison of the original and ‘translated’ texts, so you can easily turn to the modern language when you get confused. Finally, remember that the plays were meant to be performed. Read along to an audiobook, movie, or filmed version (part of the reason I’ve recommended the plays above is that all are popular enough to have some great filmed versions). None of these things are cop-outs, and most are what the plays were intended for. Take it slow, don’t be afraid to check the resources available, and try to enjoy them.

Merchant of Venice. At one point I had the entire Yale Shakespeare set. I had purchased it at an estate sale but I donated it when I moved as I didn't want to pack it up and transport it.

I'm not a literature guy. But I like Shakespeare and have read Hamlet, Macbeth, Othello and R&J. I must say these are all very interesting and full of wisdom. I say start with Hamlet.

Read, not teach, right? I feel the shakespear plays are better in the older editions. The flow is better, and it makes you think about what is said.