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.
Such a solid comment n your passion for Shakespeare shines through your words. Your point about Hamlet not having multiple plots stuck out. I read and watched A Midsummer’s Night Dream and was hopelessly lost in its meandering plot haha