Lots of interesting ideas are coursing through Shakespeare’s comedy Twelfth Night, Or What You Will. What is the relationship between love and desire? How may our conceptions of gender distract us from what we would otherwise see, admire, and desire? Might grief free us to explore things that we would not have considered otherwise?

The play explores these themes with a light hand; indeed, it can be enjoyed purely on the level of comedy. It’s considered one of Shakespeare’s funniest plays. And, as directed by Marissa Wolf and played by a fine cast of some of Portland’s best comedic talent, Portland Center Stage’s current production, which runs through December 22, mines every moment for laughs that befit a good holiday outing.

The plot centers on twins, Viola (Lea Zawada) and Sebastian (Tyler Andrew Jones), who are separated in a shipwreck, each believing the other has died. Viola, having washed up on an island where she knows no one and has no means to support herself, dons a male identity, adopting the name Cesario. The lad acquires a job as a messenger for Orsino (Setareki Wainiqolo), a duke besotted with the high-born Olivia (Dana Green). Olivia isn’t interested, however; she has cloistered herself to mourn the deaths of her father and brother.

Orsino and Olivia — the couple perhaps most suited by conventional logic — begin the play strongly committed to incompatible emotional stances: Orsino feels he must have Olivia (though he mainly seems focused on his feelings rather than on any real sense of her), and Olivia insists that grief makes her unavailable, particularly to Orsino. 

Yet Viola-as-Cesario — possibly in ways that never would have happened had she appeared in female form — shakes both of them out of their unshakable stances. Orsino quickly attaches to Cesario, treats the youth as a confidante, and is attracted to him in ways neither quite knows how to process. He sends Cesario off to communicate his pursuit of Olivia, but at the same time evinces a sort of infatuation with Cesario, relying on him as a sounding board and praising his physical parts. Perhaps Orsino’s attraction to Cesario includes an unknowing response to Viola’s ardor for him, which she hides as she feels she must, though perhaps not so well. And perhaps there is something about the young man Cesario that a woman never would have drawn from Orsino.

Olivia likewise quickly finds herself attracted to Cesario, who initially approaches her with buoyant curiosity that presumably never was part of Orsino’s suit. Suddenly Olivia finds she feels she must have this young man, surprising though that might be in terms of their differences in age and apparent class.  Her dedication to an ascetic life in response to her grief disappears, and she becomes the pursuer — all of which Viola-as-Cesario finds comical, though a bit perplexing, a tangle they must leave to gods to unravel. What Olivia finds appealing in Cesario might have been less likely to find in a person who has spent his life gendered as male.

Zawada is an able Viola/Cesario, brightly navigating all of Shakespeare’s witty comic turns. I missed seeing Wainiqolo’s take on Orsino, as he was out sick when I saw the show over its first weekend (La’ Tevin Alexander ably stepped into the role that night); watching Cesario and Orsino play out their attraction will surely be one of the pleasures of this production. Green is a fine Olivia — by turns imperious and desperate, quite unmoored by an attraction which she wasn’t expecting and which she finds herself pursuing even while it unsettles her. 

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The twins begin interacting with others before they find each other, so Olivia pursues Sebastian thinking he is Cesario — yet one wonders if his twin may have captured Olivia’s heart in ways he might not have done on his own. Though Viola means to have built Cesario out of her conception of the twin she believes she has lost, Viola may also have reached for freedom she has lacked in female form in ways that her brother needn’t have reached for. That reaching may be essential to Cesario’s appeal.

Meanwhile, some of the play’s most uproarious moments belong to members of Olivia’s household. Her uncle, Sir Toby Belch (the always agile Andy Perkins), amuses himself by overindulging in alcohol and egging on his uncomplicated pal Sir Andrew Aguecheek in his doomed pursuit of Olivia. The endlessly versatile Treasure Lunan imbues Aguecheek with comic touches uniquely their own. 

Smarter than both is Olivia’s servant Maria (Nicole Marie Green), who impresses Toby with her wit and who, for their collective amusement, hatches a plot to humiliate the self-important Malvolio (Darius Pierce), who considers himself superior to her (and everyone), and who annoys with his humorless imperiousness. I can’t ever convince myself that Malvolio deserves what he gets in this play — but Pierce brilliantly plays his very drawn-out moment of supposed revelation that his employer has romantic designs on him for every ounce of hilarity.  No laughs are left behind.

Joshua J. Weinstein brings energy to a variety of roles, and Andrés Alcalá glides knowingly through the play’s various contexts like any good Shakespeare fool, who wisely sees more and takes less seriously than anyone. Choreography by Muffie Delgado Connelly helps to capture the emotional currents moving underneath the play’s action, which run deeper than what the characters summon in Shakespeare’s sharp and clever dialogue. There is more to think about here if we wish to — or, one can simply accept this production’s invitation to play, and to laugh.