When @cryotosensei posted about Shakespeare last month, I noted that great as reading the plays is, nothing beats experiencing them, since they were written to be performed, not read1.
Live performances have been the best. Sadly, by definition, they're the hardest to share with folks. I was lucky enough to live for a long time in areas with a lot of colleges and local indie theatre troupes, which in turn meant a lot of cheap and innovative takes on the Bard. I've seen a Twelfth Night set at a Woodstock-esque music festival, with Feste as a wandering pot dealer. I've seen Hamlet played by two actors at once, a man and a woman switching off lines and actions. I've seen another Hamlet where Rosencrantz and Guildenstern are also the heads of the Players. There was A Midsummer Night's Dream in a local park that drove home the play's setting. The Taming of the Shrew that somehow incorporated "Gangnam Style" into it. Etc. And, of course, there are tons of more "traditional" takes on all of the plays, each with their own variations.
But while stage versions are the best, movies and TV are easier to find. Some that I really recommend:
Much Ado About Nothing (1993). Arguably the best comedic adaptation. Branagh was at his best as a director here, and the cast is fantastic (with the exception of Keanu Reeves, though he's not nearly as bad as some folks claim). Every scene is a delight, and it's just an incredibly re-watchable film.
The 2012 version by Joss Whedon is also a blast (and often overlooked), with some surprisingly deep performances from the cast.
Hamlet (1990). Mel Gibson started to phone in his acting performances in the late '90s, but this was before then, and while a lot of folks went in with a "oh, this is an mis-cast action star" attitude, that was, frankly, bullshit. He'd already demonstrate acting ability, and Franco Zeffirelli got a great performance out of him and the rest of the cast. Yes, Glenn Close is barely older than Gibson and playing his mother, but she's too damned good to even really mind that. Hamlet's always better on stage than screen, but this is the best version I've seen on the latter.
Romeo and Juliet (1968) and The Taming of the Shrew (1967). Okay, if it's Franco Zeffirelli, you should see it. Full-stop. Having Liz Taylor and Richard Burton in Shrew was arguably stunt casting, but it works.
(Aside: I don't love Baz Luhrman's Romeo + Juliet, but I do think it's worth a viewing, and the acting is fantastic.)
Henry V (1989). Branagh, like Zeffirelli, is always worth seeing (and there are more than just the two I list), but this was what put him on the map. Shakespeare's histories don't always hit as hard as his other plays, but this is a fantastic play adapted wonderfully.
Richard III (1995). This is the other one of Shakespeare's histories that tends to get seen a lot, at times closer to a Macbeth-style tragedy (though with more dastardly villainy). You've heard Richard's opening and closing lines ("Now is the winter of our discontent" and "A horse, a horse, my kingdom for a horse!") out of context a million times, but everything in between is fantastic. This is one of the few films that really takes a serious risk in changing the setting, but Richard Loncraine gets fantastic performances from Ian McKellen, Annette Benning, and the rest of the amazing cast.
Titus (1999). Julie Taymor's adaptation of Titus Andronicus (an incredibly brutal play, almost grand guignol in nature) is riveting and disturbing, at times closer to a horror movie than a proper tragedy (though I'm not sure any story in Shakespeare is as tragic as Lavinia's). Not for everyone, but I adore this movie, and the performances of Anthony Hopkins, Alan Cummings, Harry Lennix, and Jessica Lange.
Note that there's not a single Olivier movie listed here (other than his vocal cameo in Zeffirelli's R+J). I think Olivier was a great actor, but his Shakespeare performances seem to epitomize how not to adapt something to film. They feel painfully like filmed versions of stage plays, without the energy that a live performance brings. I can appreciate the soliloquies on YT, but can't enjoy the entire experience.
There are also a TON of great films that are inspired by Shakespeare. A few that I love:
Throne of Blood
10 Things I Hate About You
Kiss Me Kate
Rosenkrantz and Guildenstern are Dead
Ran
West Side Story
My Own Private Idaho
Scotland, PA
Forbidden Planet
I'm also a huge fan of the Canadian TV show Slings and Arrows, which follows a festival (modeled on the Stratford Festival) as it puts on performances of Hamlet, Macbeth, and King Lear. Absolutely some of the best TV ever made. The BBC also did a series called ShakespeaRe-Told that had some fascinating updates and takes (and a great cast).
I'm sure other folks have recommendations I'm either forgetting or have never seen (or even heard of). Let me know some fantastic ones to keep an eye out for, or nifty local productions you've seen.
Footnotes
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Shakespeare famously barely used stage directions, other than noting characters entering and exiting the stage. And with the exception of the famous "Exit Pursued by a Bear" line, few are even interesting. Compare this to A Streetcar Named Desire, which begins with a Hart Crane epigraph followed by three full paragraphs plus a bonus setting the scene, followed in turn by a paragraph bringing Mitch and Stanley onto the stage and describing them. Tennessee Williams assumed someone would read his play, even if they never saw it on stage or screen. To be clear, Streetcar is a masterpiece; this just demonstrates the different approaches. ↩