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Richmond Shakespeare Theatre’s practice of “doubling” — having each of its actors play two or three roles in a show — has always led to some interesting juxtapositions. Its current production of “Measure for Measure” may present the most fascinating and artistically rewarding combinations yet.

In this complex consideration of moral gray areas, Andrew Hamm portrays both the strict Duke’s deputy, Angelo, who must crack down on the reprobates of Vienna, and the unfortunate gentleman Claudio, who gets cracked down upon. Both of these characters are fraught with inner conflict, and it’s a tribute to Hamm’s considerable skills that he is able to make each man’s trajectory riveting and distinct. He even throws in for good measure an amusing comic turn as an elderly constable.

Hearing that Claudio has been sentenced to die, his novitiate sister, Isabella, leaves the nunnery to plead for his life. Angelo makes her a devil’s bargain: If she sleeps with him, he’ll free her brother. As Isabella, Liz Blake is convincingly enchanting and proves her acting mettle in the extreme emotional rollercoaster her character must ride.

Spurring the plot into greater complication is Vincentio, the Duke (David White), who disguises himself as a friar to spy on the proceedings. White doesn’t quite do enough to differentiate the Duke from the pimp Pompey, but he salvages his performance in some exceptional final scenes.

In other supporting roles, Julie Phillips makes her biggest impression as the bawdy Mistress Overdone, and while John Moss’ near-farcical take on the opportunistic Lucio sometimes seems to belong in a different play, it’s also consistently hilarious.

As is befitting one of Shakespeare’s “problem” plays, this production has some issues with the mix of comic and melodramatic elements. But the overall effect is a bracing — and gratifying — journey down a murky moral path. S

Richmond Shakespeare Theatre’s “Measure for Measure” at Second Presbyterian Church, 5 N. Fifth St., runs Thursday-Saturday at 8 p.m. through March 2 with Sunday matinees at 2:30 p.m. Tickets are $24. Call 232-4000 or visit www.richmondshakespeare.com.

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