Michael Kahn speaks in a soft, gravelly baritone and punctuates his conversations with a mischievous little laugh: the telltale sign of a man who enjoys what he does. That joy has been apparent over a theatrical career whose capstone achievement — the Tony-honored Shakespeare Theatre Company — is soon to start a wholly unique chapter in its 33-year history. That is to say, an existence without him.

The Brooklyn-born Kahn, now at 81 the dean of artistic leadership in Washington, is the chief reason citizens of the nation’s capital can boast to play-loving friends elsewhere that they live in a city offering some of the most incisive and comprehensive classical theater on the continent. Since his local start in 1986 with a production of “Romeo and Juliet” at what was then the Shakespeare Theatre at the Folger Shakespeare Library, Kahn has turned the Potomac into a veritable tributary of the Avon. Where bardolatry is concerned, he’s the enabler-in-chief: From high school English students to retired Supreme Court justice Sandra Day O’Connor, Kahn has been the guy enticing audiences with an Elizabethan fix.

He’s about to unveil the final directorial effort of his tenure in Sidney Harman Hall, the aesthetically elegant, though tough to fill, 775-seat theater erected in 2007, at the height of the company’s self-confidence. After this, the job passes to Simon Godwin, from London’s National Theatre, who takes over in August.

And true to sly form, Kahn has decided not to sign off with something by Shakespeare; he’s reaching back further, to Aeschylus’s ancient tripartite tragedy, “The Oresteia,” in a translation by Ellen McLaughlin. This is, among other things, a nifty way of reminding us of one of the cornerstones of Kahn’s term as classical man-at-the-wheel: attempting as often as possible to drive in an unexpected lane.

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“I liked to do impossible plays,” Kahn said recently, reflecting in his office in the company’s administrative suite on Capitol Hill. “That’s what I would get up in the morning wanting to do.”

To reflect on Kahn’s record is to reexperience some of one’s own pleasures in his spaces, Harman Hall and the smaller — and, in many ways, more satisfying — 450-seat Lansburgh, to which the company moved from the Folger Library in the early 1990s. Before it became voguish, Kahn was inviting to his stage actors with classical chops who had achieved success in other mediums: Stacy Keach, Patrick Stewart, Tom Hulce, Avery Brooks, Hal Holbrook, Richard Thomas, Kelly McGillis. And he installed a cadre of others who became his de facto repertory company: such skilled tragedians and farceurs as Edward Gero, Floyd King, Ted van Griethuysen, Franchelle Stewart Dorn, Helen Carey, Nancy Robinette, Tana Hicken, Wallace Acton, David Sabin, Sarah Marshall, Tom Story, and on and on.

Kahn has directed 63 productions for his company, 36 of them by Shakespeare (including three “Hamlets,” two “Macbeths,” two “Richard IIs” and two “Richard IIIs”). His “Othello” in 2005, with Brooks in the title role, was noteworthy for Patrick Page’s cold, internalized Iago. The performance highlighted one of Kahn’s own strengths — encouraging actors to apply psychological nuance to characters, such stuff as their playwright-creators might never have dreamed on.

In 17 seasons of watching Kahn’s work, though, the pieces that remain most vivid are not the great tragedies and history plays, but those “impossible” plays: an improbable stab at “Lorenzaccio,” a 19th-century French “closet” play; a staging of Friedrich Schiller’s “Wallenstein,” in an adaptation commissioned from poet Robert Pinsky; a compressed version of Eugene O’Neill’s “Strange Interlude,” often regarded as unproducible. None were perfect, and a few, including Christopher Marlowe’s “Tamburlaine,” the drama with which Kahn chose quixotically to open the Harman, were disasters. But a straight diet of chestnuts, even Shakespearean ones, is bad for a theater lover’s digestive system. You need to sample stranger fruit, too, and Kahn allowed us to sample the more exotic selections, even if the results didn’t always enrich the company’s coffers.

As an artistic director, Kahn cultivated some fine younger directors: Rebecca Taichman, David Muse, Ethan McSweeny. Taichman would go on to win a Tony, as director of Paula Vogel’s “Indecent”; Muse and McSweeny, two of Kahn’s former assistants, now run their own theaters. From his concurrent term as head of Juilliard’s acting program in New York, from 1992 to 2006, he introduced a slew of young actors to Washington audiences, none more excitedly than one by the name of Daniel Breaker, who appeared in several Shakespeare Theatre Company comedies (and is now playing Aaron Burr on Broadway in Lin-Manuel Miranda’s “Hamilton.”)

And few collaborations in this country between a classical director and a (living) playwright have proved more advantageous than that of Kahn and David Ives. Ives’s comedic adaptations for Kahn — “The Liar,” “The Heir Apparent,” “The School for Lies” — have time and again proved a major bonus for the company’s patrons.

For me, the best of Kahn’s senses has been his comic one, whether filtered through the farcical constructions of Ben Jonson’s “The Silent Woman” or Tom Stoppard’s elevated wit (in “The Real Inspector Hound”). High-concept, modern-dress Shakespeare can on occasion feel as if a director looked at a cat and decided to dress it like a giraffe, but when a transposition works — as it did for Kahn’s resetting “Love’s Labor’s Lost” amid denizens of the counterculture of the ’60s — the reinvention can be magically delicious.

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“It’s a satire on a bunch of young men,” Kahn said of the 2006 production, which he would end up taking to a global Shakespeare festival in Britain. That little laugh returned to finish off Kahn’s sentence, as he recalled where he thought a scruffy gaggle of risible 1960s types would have trundled off to: “To India!” he declared.

“Shakespeare didn’t care where Illyria was,” he added, referring to the locale of “Twelfth Night”; last season, McSweeny set it — quite beautifully — in an airport departure lounge. “If an idea illuminates something about the people in the play, then that’s good.”

It seems to have become more difficult of late to both fill out classics consistently with the caliber of actors Kahn is after and to bottle the fervor of audiences for works that often require some level of familiarity — if not patience. Several years ago, the company began to add older musicals to its repertory, which boosted the box office and sometimes even registered as inventive, as did a “Camelot” last season, directed by Alan Paul. Still, Kahn’s legacy is unlikely to be embedded with a show tune. It is the play, always the play, whether by Will or Williams, that sparked his imagination.

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“That was always the goal — to get the best people and to do the best work we could do,” he said. Without a trace of a laugh. The work of turning the heads in a city full of smart ones to the texts of great dramatists is serious business. And Washington has Kahn to thank for his rigor and passion, and especially, his dedication to impossible plays.

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