Character descriptions:
Viola: 20s, any gender. Our plucky protagonist who survives a shipwreck, finds work with a wealthy club owner, and then finds themself in the middle of a love triangle. Clever, practical, resourceful, charming, and resilient. Cautiously optimistic about the world, very good at thinking on their feet. Must be able to handle a weapon with confidence!
Orsino: 20s–early 30s, masc. A wealthy speakeasy owner and idle rich cad who pines after first Olivia, and then Viola. Very much a Jay Gatsby type–wistful and romantic, but also jaded and misguided, more in love with the idea of love at first.
Olivia: 20s–early 30s, femme. Orsino’s ex, a high society girl still mourning her brother’s death. More Jordan Baker than Daisy Buchanan–spirited, witty, sensitive, and does not suffer fools gladly. Finds herself falling in love with Viola’s alter ego and slowly starts to re-emerge back into the world because of it.
Sebastian: 20s, any gender. Viola’s twin, though dead after the shipwreck and now trying to reunite with them somehow. More serious than Viola, determined, fiercely loyal, and hot-headed. Inspires a great deal of loyalty from their loved ones in return. Must be able to handle a weapon with confidence!
Feste: Later 30s–40s, any gender. A street musician and friend of Olivia’s father, confidante to her and later Viola. Takes pride in being a “fool” and takes very few things seriously, but is always the smartest and savviest person in the room. Exudes “eccentric uncle” energy. Must be able to sing and play an instrument!
Toby Belch: 30s–40s, masc. Olivia’s cousin who mooches off of her while brewing and selling moonshine while her back is turned. Fancies himself a mentor to Andrew. Constantly drunk, loves a good party, and seems not to have a care in the world, but has a vindictive streak a mile wide. Must be able to handle a weapon with confidence!
Andrew Augecheek: 20s, masc. Toby’s protege, an “upper-class twit” who keeps getting dragged into trouble because of some questionable taste in friends. Naive, earnest, and impulsive–tries to believe the best in people no matter how much evidence to the contrary. Must be able to handle a weapon with confidence!
Maria: 30s–40s, femme. Olivia’s housemaid and chaperone. Close associate of Toby, Andrew, and Feste. No-nonsense and practical on the outside, crafty and willing to spearhead all kinds of shenanigans on the inside. Usually quite patient, but can only be pushed so far.
Malvolio: 20s–30s, masc. Olivia’s valet and Toby’s nemesis, a legacy hire whose family has served Olivia’s for generations. Holds himself above the rest of the household and feels entitled to Olivia’s love because of it. A huge narc who’d never dream of breaking any rule (unless it suited him, of course). Stuffy, dour, and almost allergic to fun.
Antonio: 20s, any gender. A recently-arrested pirate on the run from both the law and Orsino. Even more loyal and hot-tempered than Sebastian, desperately looking for any safe foothold in life and will cling to it for all they’re worth. Hopelessly in love with Sebastian after they showed them kindness, would kill for them in a heartbeat. Must be able to handle a weapon with confidence!
Curio: 20s–40s, any gender. Orsino’s valet and potential “fall guy”. Enjoys a very tense relationship with both him and Viola, but never lets their true feelings show. Quiet and unassuming, but also extremely observant and clever.
Captain/Bouncer: 30s–50s, masc. The Captain of Viola and Sebastian’s ship/the Bouncer at Orsino’s speakeasy. Strong, reliable, and unfuckwithable man of few words.
Ensemble: Any ages, any genders. Illyria’s partygoers and resident jazz band, providing a lively atmosphere to all the club scenes, occasionally providing backup for Feste. Must be able to dance and/or play and instrument!