For the second show of its inaugural season, the Cary Players chose another classic: Twelfth Night (1601-02). This timeless five-act romantic comedy by Elizabethan dramatist William Shakespeare (1564-1616) presents a number of major challenges for a fledgling community theater to overcome.

They include: finding a sufficient number of local comic actors and actresses who can squeeze all the juice from their plum roles, subduing the Tar Heel twang and polishing the diction of the cast, coaching cast members in the fine points of the flowery and sometimes arcane Shakespearean language, and creating plausibly authentic Renaissance costumes and scenic backdrops for the mythical kingdom of Illyria, where romance is in the air and the immortal bard creates a veritable three-ring circus of lovers and fools.

To add another degree of difficulty, the Cary Players will perform Twelfth Night at the Sertoma Outdoor Amphitheatre in Fred G. Bond Metro Park in Cary, NC. Veteran Triangle actor/director and Cary Players co-founder and president Herman LeVern Jones will have his hands full staging Twelfth Night under the stars. Director Herman Jones says his production team — assistant director Kurt Benrud, musical director Penny Drew, technical director Neil Williamson, costume designers Diana Waldier and David Serxner, and prop master Dave Merritt — is up to the challenge.

“Directors always dream about directing Shakespeare,” Jones claimed in preshow publicity, “and selection of this play for Cary is the fulfillment of a longtime wish.”

Jones added, “Working with the language and the potency of Shakespeare’s comedy is not only challenging, but very thought-provoking and mesmerizing for both myself and the cast. The Cary Players is a professional community theatre group, and I feel we must challenge ourselves annually with Shakespeare. We are very happy to whet our community’s appetite with such a challenging production, and look forward to having everyone share it with us.”

Probably based on the 1531 Sienese comedy Gl’ingannati (The Deceived), Twelfth Night, or What You Will, is widely considered to be one of Shakespeare’s finest comedies. It features some of the Bard’s favorite comic devices: shipwreck, twins, cross-dressing, and forgery.

For example, when a trademark Shakespearean shipwreck off the coast of Illyria separates identical twins Viola (Lynne Guglielmi) and Sebastian (Brian Graves), each assumes that the other perished. A stranger in a strange land, Viola dons men’s clothing, calls herself Cesario, and takes a job in the court of the lovelorn Duke Orsino (David Bland). The duke uses Cesario as a go-between to his beloved Olivia (Jennifer Lukas Joyner), who rebuffs her sovereign’s romantic overtures, but falls in love with the handsome (cross-dressing) stranger.

Viola/Cesario, who by now has a sizable crush on Orsino, finds herself in a pickle about how to reveal her true feelings — and the fact Cesario is really Viola. Then Sebastian arrives — unbeknown to Viola — and is immediately confused with Cesario, and this sublime comedy of mistaken identity scales new heights of hilarity.

Meanwhile, some of the scurvier members of Olivia’s household — the jester Feste (Kurt Benrud), Olivia’s gentlewoman in waiting Maria (Debra Grannan), Olivia’s drunken ne’er-do-well uncle Sir Toby Belch (Wilson Pietzsch), his friend the prissy Sir Andrew Aguecheek (Thom Haynes), and Olivia’s servant Fabian (Kathryn Jenkins Smith) — conspire to play a cruel practical joke on Olivia’s sanctimonious, stuck-up steward Malvolio (Matt Schedler). They plant a phony love letter — ostensibly from Olivia — where Malvolio will be sure to find it. In it, “Olivia” confesses her attraction to the insufferably pompous steward and says that, in order to win her love, he should do a number of things that Maria knows Olivia hates with a white-hot passion. When Malvolio does as he is bidden, Olivia predictably tongue-lashes him and banishes the totally bewildered steward from her sight — while the audience is rolling in the aisles.

Staging Twelfth Night has been a wonderful experience, Herman LeVern Jones told Robert’s Reviews in the telephone interview Tuesday afternoon.. “I love the comedy,” Jones confesses, “and the deception that’s portrayed in this production. It’s just been a delight to work on this production, because of the language.

“In putting this production together,” Jones says, “I’ve had to work with cast in which some of them were more knowledgeable than others. The points of discovery were very genuine and very poignant, because none of the cast had — up until this point — worked on a production of Twelfth Night. Many of them had seen a production of Twelfth Night, but they had not worked a production of this magnitude and scope.”

Jones adds, “Working with the language and the iambic pentameter and discovering the meaning of this [play] was really wonderful, because [Twelfth Night] has great revelry, playfulness, and some serious scenes in it. It’s kind of fantastical, too. It makes the exploration of Shakespeare exciting when you can get all of these elements in one production.”

The Cary Players production of Twelfth Night should please Shakespeare purists, Jones says, “We’re keeping the original setting,” he explains. “We have not cut the script. It’s the full-length Twelfth Night.”

Jones’ directorial philosophy about staging a Shakespeare play is simple: “Let’s do what’s there and take the time it takes to do it,” he says. “Seeing [Twelfth Night] fully done, we will get the full meaning. The language is somewhat archaic; however, I think that the blocking and the choreography will bring the meaning to full light. We also have what we call ‘Feste’s Cheat Sheet’ that we will pass out to the audience that will help them understand these archaic references.”

But Jones admits that “working outdoors, working in an amphitheater” is no stroll in the park.

“The past week has been wet,” he sighs over the phone while band-saws buzz in the background, “so we have to find every available dry moment to put the set together. We’ve got a fully developed set and costumes…. However, that makes it fun, too. We’ve rehearsed five or six days in the rain. Misty and wet, but fun.”

The Cary Players present Twelfth Night Wednesday-Friday, May 28-30 and June 4-6, at 8 p.m.; Saturday, May 31 and June 7, at 2 and 8 p.m.; and Sunday, June 1 and 8, at 3 p.m. in the Sertoma Outdoor Amphitheatre in Fred G. Bond Metro Park, 801 High House Rd. (between Cary Parkway and Northwest Maynard Rd.), Cary, North Carolina. $12 ($8 students and seniors and $10 groups of four or more). 919/836-0866 or tickets@caryplayers.org. http://www.caryplayers.org/newsite/shows.htm.