Setting a classic Shakespeare play in contemporary times is always a gamble, which makes the very idea of a 1950s casino backdrop for Comedy of Errors such a high-stakes bet. And director Bill Rauch bets big with his surprising production, the highlight of the early-season plays at the Oregon Shakespeare Festival.

In Rauch's Comedy, actors adopt style cues from the Rat Pack, decked out in satin dinner jackets and cotton-candy-colored sheaths, pompadours and Aqua Velva-sprayed flips. They filter Shakespeare's language through garish accents stolen from a multicultural grab bag--a mix of Italian mobster, cowboy redneck, urban black princess, Asian saleswoman, even the "golly, gee" wonder of hickster tourists.

The sharp humor begins with the first speech by Solinus, the Duke of Ephesus (Mark Murphey), who cops a Sopranos attitude as he recounts the wild tale of mistaken identity to his trench coat-wearing henchmen. An old cowboy, Aegeon (Clive Rosengren), risks his life by entering a rival country in search of long-lost loved ones: his wife, one of his twin sons, and his son's servant, also a twin. Thus ensues a rash of coincidences: Adriana (Crystal Fox) thinks she's going crazy after strange encounters with a man who appears to be her husband, Antipholus (Ray Porter), and his servant, Dromio; another twin, (Christopher DuVal) is repeatedly boxed for screw-ups he didn't commit. The audience holds the trump card: the knowledge that there are two sets of identical twins wandering through a casino town on this very night.

In less-assured hands, the play's cliché, gaudy gimmicks--all those saturated colors! all those accents! all those stereotypes!--might seem an attempt to trick out Shakespeare for the Clueless generation. Instead, Rauch and his ensemble deliver a raunchy, spirited interpretation that transforms a bauble of a poetic farce into a political comedy still relevant in our grim age.

Gambling, or more specifically, the street hustle, is the language spoken in Suzan-Lori Parks' Topdog/Underdog, which plays through this month at Ashland's intimate New Theatre. Threaded throughout the lengthy drama is the call-and-response of an ongoing game of three-card monte. The patter of the con serves as a chorus to bind--and cheat--brothers Lincoln and Booth, who remain defeated by their personal and cultural history. Working in a cheap arcade, Lincoln is assassinated every night while playing his namesake in white face. "A sit-down job," he emphasizes, "with benefits." His brother subsists on "boosting"--stealing, that is--and boasting about his plans for a sexual reunion with an ex-girlfriend, as well as his schemes to succeed at cards.

Some critics label Parks' plays as "symbol-laden thickets," but in an interview last year the playwright dismissed talk of the mythology embedded in her characters' names as "just a brain fart." That's the risky hot air of Topdog--the play's not completely successful, darting moves between the grit of its hypertuned language and more stagey dips into historical allegory.

The sturdiness of the Ashland production rests in the pairing of the blast-off energy of Kevin Kenerly's dread-locked younger brother, Booth, matched with the slower-to-flare rage of G. Valmont Thomas' big-boned Lincoln. One example of how finely drawn these characters are: Watch how Kenerly subtly portrays his character's neurosis through repeated cuticle biting, each pull of fingers to mouth another chance to telegraph the coming explosion.

There's less subtlety displayed in another duet of family stories, 1959's A Raisin in the Sun, which still plays better than 1927's The Royal Family, a dusty chestnut depicting the Cavendish family, a tribe of actors based loosely on Drew Barrymore's ancestors.

At the center of Raisin is Walter Lee Younger, a flawed son who betrays his family with his hunger for chasing after wealth, and Chris Butler's fluid physicality is all energetic movement, his stylized gestures too big to make his character as sympathetic as needed. That said, Butler's Younger moves well in concert with his wife, Ruth, played with becalmed dignity by Crystal Fox, and is particularly successful in scenes with Aisha Kabia, who offers a charming, intellectually flighty turn as the family's Africa-centric younger sister, Beneatha.

Yet this Raisin and its lesser Ashland cousin, The Royal Family, belong to the grande matriarchs at the heart of each story--Pat Bowie's fiercely loving Lena Younger, and Dee Maaske's preening Fanny Cavendish. Plot aside, maybe that's the most successful message offered by these plays: a reminder of what strong women actors can make of such hearty roles. May history--and the Oregon Shakespeare Festival--continue to provide such meat.

Angus Bowmer Theatre.Through Oct. 31.

Topdog/UnderdogNew Theatre.Through June 25.

A Raisin in the SunAngus Bowmer Theatre.Through Oct. 30.

The Royal FamilyThrough Oct. 30.

Also this season:A rare chance to see the trilogy of Henry VI historical plays, set during the War of the Roses, a battle for the throne of England.

For complete schedules, visit www.osfashland.org , or call (541) 482-4331.