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If “All’s Well That Ends Well” is, as some critics insist, a “problem comedy,” then director Drew Martin, by setting the play in the Mafia-land of television’s popular series, “The Sopranos,” has smeared, if not completely erased, the comedy’s challenges by darkening the dramatics and upping the merriment, giving Stage Left Theatre a most happy surprise.

In this contemporary setting, it is easier to believe that such a Shakespearian heroine as Helena would be not only allowed, but assisted by familial figures, to publicly pursue, marry and then trick into marital consummation the recalcitrant, reluctant, callow youth of her choosing. Melanie Derleth makes the momentous task of playing Helena seem like a walk in the park; every moment is real and sure, and for the little time she is offstage, the world is a gloomier place. Luke Daigle throws himself fervently at the playing of the most despicable leading youth in the canon; Daigle plays Bertram’s reformation from the heart.

Rich Logan’s King is elegant and earthy, kind and killing, replete with kissable ring and an Italian suit. Sandy Elias is a warm-and-fuzzy Lafew with a backbone, and Sean Sinitski’s hysterical, knowing Lavatch is a lesson in acting Shakespeare’s wise clowns. Michael Reyes both amuses and frightens, expertly delineating the roles of the Duke and the Astringer.

Perhaps the most ubiquitous success of the production is Jeremy Trager’s Parolles. Expert at playing an undercurrent of malevolence, Trager makes believable Parolles’ transition from cocksure self-absorption to defeated self-awareness. Trager is the rare bird who built a career as a character actor before he was sufficiently of age, and is making the leap into his majority with great agility.

If Martin’s bold move to have Bertram draw a pistol on the King and yet live left me unnerved, his boldness in playing for “Jersey Shore”-comedy the Diana/Widow scenes succeeds mightily; Heather Chrisler and Kimberly Logan, respectively, out-Melanie Griffith Melanie Griffith in “Working Girl.” (Aaron Hunt)

Stage Left Theatre at Theater Wit, 1229 West Belmont, (773)975-8150, stagelefttheatre.com, $20-$30. Through May 24.