The 9 best plays of the first half of 2014

This spiky Stephen Sondheim musical is one of the composer's most recently completed works, which seems an odd thing to say about a 24-year-old piece by a man who's still active (we're waiting patiently for whatever it is he's supposedly working on with playwright David Ives). The fantasia about a convention of every individual who's killed (or tried to kill) an American president is also one of Sondheim's most divisive, but one of my favorites, and Kokandy Productions' intimate staging and stacked ensemble hit their target with more precision than I've ever seen. It continues through July 20 at Theater Wit.

I tend not to include touring shows in my year-end best-of lists, since they're usually limited to a ranked top ten and there are almost always ten homegrown shows I'd rather honor. But this mid-year roundup is a new thing for me, and Michael Urie's performance in Buyer & Cellar is: A) not the kind of thing that usually gets a Broadway in Chicago slot and B) the kind of fully-inhabited comic tour de force that doesn't come along every year. If Jonathan Tolins's script, which imagines a struggling, gay L.A. actor hired to play along in Barbra Streisand's private playhouse, has any holes, Urie papered over them with consumate skill.

This spring saw two new plays by young Chicago writers, passionately performed by non-Equity casts, casting light on all-too-real issues in the Chicago Public Schools system via fictional means. Ike Holter's righteous, raucous Exit Strategy, staged by the rising Jackalope Theatre Company and depicting the frustration of faculty members at a high school facing impending closure, got more hype (perhaps because it coincided with the abortive return of Holter's 2012 hit, Hit the Wall). But the hype was deserved, and thankfully led to an impending remount July 30–August 29.

Director Kimberly Senior, soon to make her Broadway debut with Ayad Akhtar's Disgraced, started the year by bringing a new light—and, to a certain degree, a new lightness—to Ibsen's story of stifling domesticity. Nicholas Rudall's expressive translation and Kate Fry's flinty portrayal of Hedda are still, you could say, shooting around my head.

The Hypocrites' reduced-cast production of Sondheim's 1986 fractured fairy tale played up the juvenalia in the first act with balloons and sippy cups, all costume-trunk play-acting. Director Geoff Button's concept might have sounded on paper like artificial coloring, but it made Act II's post–happy-ending destruction all the more harrowing, played out by a game ensemble of singing actors whose quick-changes actually made the story more resonant.

This slippery, compelling study of a massively complicated child-custody case that's further muddied by massively complicated bureaucracy was the sharpest work I've seen from playwright Rebecca Gilman. This fall, director Robert Falls takes the Goodman's production—expected to include the Goodman's entire ensemble cast, led by the superb Mary Beth Fisher as the harried social worker handling the case—to Los Angeles's Kirk Douglas Theatre.

Marisa Wegrzyn's new comedy, about a trio of weathered flight attendants on layover at a crappy O'Hare hotel and the teenage boy who gets roped into their evening, benefited from a tight-knit cast that showed as much affection for their sometimes cynical characters as did the playwright and director Shade Murray. Wegrzyn, Murray and the four actors—A Red Orchid ensemble members Natalie West, Mierka Girten and Kirsten Fitzgerald along with the winning Matt Farabee—illustrated how simply being there can mean the world to someone else, whether or not we’re at the same point on our journeys.

The other dark comedy to take on CPS woes and teachers' frustrations was actually the first to open, by just a few weeks. Written by Joe Zarrow, himself a former CPS teacher, and co-produced by Stage Left Theatre and Theatre Seven of Chicago, Principal Principle dealt not with a school facing closure but a school facing simple realities. Kay, a Teach for America–type who arrives at the South Side's fictional Chinua Achebe High School Academy, serves as our surrogate among the English department's veterans, negotiating ever-changing standardized testing requirements and a principal whose blame-shifting to City Hall provides a proof of the Peter Principle. Happily, Principal Principle has also earned an upcoming remount at Theater Wit, July 17–August 17; it deserves your summer enrollment.

Again, I've tended to exclude touring shows from my year-end top-tens, a policy I think I've applied as evenly to Chicago Shakespeare Theater's invaluable World's Stage series as I have to Broadway in Chicago's commercial projects. But as I said with regards to Buyer & Cellar, this midyear roundup requires new rules, and also, did you see Kneehigh's swoonworthy Chicago debut? It's been suggested to me by knowledgeable peers that the Cornish company's inventive take on this ancient legend actually worked better in CST's Courtyard Theater thrust configuration than it has elsewhere on its extended tour. I'd believe it; the transparent theatricality of Emma Rice's staging and the romance between (as I wrote in April) "stupidly charismatic leads Andrew Durand and Etta Murfitt" was all the more magical because we could see the strings from all sides.