Chicago History Through Theatre

We love Chicago and find its history fascinating. Even before we moved to Illinois, we regularly made the ten-hour drive from Tennessee to enjoy the architecture and culture of Chicago (remember Rose Records and Kroch’s & Brentano’s Bookstore?). We have since gained a lot of our knowledge of Chicago’s history from plays set in Chicago, so we thought it would be fun to outline a history of Chicago through theatre. Accordingly, in compiling this list we have limited our selection to plays that illustrate some significant chapter of Chicago’s history or an important aspect of its ethos, as opposed to stories that could have happened anywhere, or at least any large city.

(in roughly chronological order historically)

Scene from Underscore Theatre's Haymarket
Scene from Underscore Theatre’s Haymarket (photo by Evan Hanover)

Haymarket: The Anarchist’s Songbook by Alex Higgin-Houser and David Kornfeld, directed by Elizabeth Margolius, produced by Underscore Theatre Company in 2016: Sometimes you have little idea what to expect when you enter a theatre. In this instance we had no prior knowledge of the authors, director, or producing company, and only a vague awareness of the subject matter, the infamous Haymarket affair of 1886. Much of the story is conveyed through songs in a variety of styles typical of the period but with more sophisticated lyrics, and with the actors providing instrumental accompaniment on guitars, banjos, and the like. Parts of the story are told from the perspective of former slave Lucy Parsons, wife of defendant Albert Parsons, who had moved to Chicago from Texas because of intolerance of their interracial marriage there. Repercussions of the Haymarket affair were felt nationally and internationally, and led to the establishment of May Day as the international celebration of labor and various related social and political causes. As often happens, theatre enlightened us about a significant slice of history while also entertaining us, in this case with a powerful and fervently performed musical.

Scene from the 2015 production of Burning Bluebeard
Scene from the 2015 production of Burning Bluebeard (photo by Evan Hanover)

Burning Bluebeard by Jay Torrence, directed by Halena Kays, produced by The Ruffians in 2013 and The Hypocrites in 2015: The Iroquois Theatre fire of 1903 was the deadliest single-building fire in Chicago (or U.S.) history, with more than 600 killed. In 2011 The Ruffians had the inspired idea of recreating the fateful matinee performance of Mr. Bluebeard that was interrupted by the outbreak of fire, and complete it as a tribute both to the performers (almost all of whom survived) and the audience in attendance (hundreds of whom died). The vaudeville/burlesque style of the original show was a perfect match to the acrobatic, clowning style of The Ruffians, performed mostly in pantomime. The show was a great success with both critics and audiences, leading to a remounting at Theatre Wit in 2013 and again in 2015 in conjunction with The Hypocrites at The Den Theatre’s Heath Main Stage. We saw both of these remounts, which hauntingly captured the mirth of the original performance style juxtaposed with the pathos of impending doom. This magical presentation was truly a gift to the audience. (Another historic Chicago tragedy, the 1915 Eastland disaster, is included in our list of memorable ensembles.)

Scene from Oracle Theatre's The Jungle
Scene from Oracle Theatre’s The Jungle (photo by Joe Mazza)

The Jungle by Matt Foss, adapted from the novel by Upton Sinclair, directed by Matt Foss, produced by Oracle Productions in 2015: In the late 19th and early 20th centuries, Chicago had its share of greedy capitalists who exploited laborers working in inhumane conditions, which in turn spawned exposes by muckraking journalists. One of the most famous of these was Upton Sinclair, who took on Chicago’s meatpacking industry in his 1906 novel The Jungle, which was adapted for the stage and directed by Matt Foss for Oracle’s production. Staged in Oracle’s tiny performance space with their trademark intimacy, the desperation of the mostly immigrant workers and the brutality of their working conditions were viscerally conveyed. The slaughter of livestock was cleverly represented by slashing outlines of cattle stamped on rolls of brown meatpacking paper, the seemingly endless supply of which also suggested the monotony of this mind-numbing job. The Jungle received Jeff Award nominations for best production, ensemble, direction, adaptation, and original music.

PJ Powers and Terry Hamilton in Timeline Theatre's The Front Page
PJ Powers and Terry Hamilton in Timeline Theatre’s The Front Page (photo by Lara Goetsch)

The Front Page by Ben Hecht and Charles MacArthur, produced by TimeLine Theatre Company in 2011: Chicago has long been a home of many colorful journalists, from crusading muckrakers to lurid sensationalists. This classic comedy mixes three Chicago specialities: crime, politics, and journalism. For playwrights Hecht and MacArthur, the play was an affectionate tribute to their own careers as reporters in Chicago and the colorful characters they encountered in all three categories. The story has been the subject of many permutations on stage and in films, including the classic movie His Girl Friday, but our favorite production of the original stage play was produced by TimeLine in 2011, directed by Nick Bowling. The large cast of many TimeLine regulars, led by Terry Hamilton as editor Walter Burns and PJ Powers as ace reporter Hildy Johnson, masterfully executed the rapid-fire dialogue and mined the script for every laugh while also effectively conveying the spirit of the times.

Cast of Happy End by Brown Couch Theatre
Cast of Happy End by Brown Couch Theatre

Happy End by Kurt Weill, Bertolt Brecht, and Elisabeth Hauptmann, adapted by Michael Feingold: This “melodrama with songs” is about gangsters in Chicago in the 1920s (or at least Chicago as imagined from Weimar Germany) who become involved with a Salvation Army mission (echoing Major Barbara and anticipating Guys and Dolls) while pulling a bank heist. We first saw a production at the Shaw Festival in Canada in 2003, where it was so popular with audiences that it was remounted for their 2005 season (and we saw it again). The only time we’ve seen it in Chicago was a resource-limited but spirited production in 2006 by Brown Couch Theatre Company, which benefited from the intimacy of the Raven studio space and a highly capable cast that included Andrea Prestinario and Heather Townsend, plus sterling piano accompaniment by Andra Velis Simon. Another favorite musical in a similar vein is Kander and Ebb’s classic Chicago.

Scene from the premiere production of A Raisin in the Sun
Scene from the premiere production of A Raisin in the Sun (photo from Friedman-Abeles Collection)

A Raisin in the Sun by Lorraine Hansberry: Housing has been a thorny social, economic, and political issue throughout much of Chicago’s history. Prior to enactment of the federal Fair Housing Act in 1968, restrictive covenants were used in Chicago to limit where ethnic minorities could reside, especially African-Americans who had migrated from the South following the Civil War. The result was intense overcrowding and often squalid living conditions in dilapidated tenements. Against this backdrop, playwright Lorraine Hansberry wrote the classic A Raisin in the Sun based on her own family’s experience in seeking a better life, even it that meant moving to a white neighborhood where they might be unwelcome. The play also examined other issues, such as an absent father (in this case due to his premature death) and the yearning by some African-Americans to reconnect with their African heritage. The play premiered in Chicago in 1959 before going on to a successful run on Broadway, making Hansberry the first black female playwright to have a play on Broadway. For an account of our favorite productions, see our list of definitive productions. The success of Raisin has spawned a number of spin-offs, including Genesis, a prequel about the Younger family by U of Illinois alum Mercedes White, and Clybourne Park by Bruce Norris, about the white family who sold their home to the Youngers. For more on productions of Clybourne Park, see our list of surprises.

Sandra Delgado in La Havana Madrid
Sandra Delgado in La Havana Madrid (photo by Joel Maisonet)

La Havana Madrid by Sandra Delgado: Teatro Vista’s “coming soon” description of La Havana Madrid made us eager to see the show, but in no way prepared us for the epic, heroic, and deeply affecting stories of the people who frequented the nightclub La Havana Madrid in the 1960s (located at Belmont and Sheffield, just south of Wrigley Field). Playwright and lead actress Sandra Delgado grew up near there, and the inspiration for the play came from her parent’s reminiscences about the club. The play recreates its ambiance and its music (led by the legendary Roberto “Carpacho” Marin), while depicting true stories of Cuban, Dominican, Colombian, and Puerto Rican immigrants who moved to Chicago at great personal risk in search of opportunity. Playwright Delgado, the inspired cast, and director Cheryl Lynn Bruce wove those individual narratives into the most beautiful history lesson we’ve ever experienced in a theatre, with the fabulous music of La Havana Madrid as the soundtrack.

Scene from The Project(s) at American Theater Company
Scene from The Project(s) at American Theater Company (photo by Michael Brosilow)

The Project(s) by PJ Paparelli and Joshua Jaeger: Chicago’s (often failed) attempts to provide public housing for the disadvantaged is tellingly recounted in The Project(s), a brilliant piece of oral history and documentary theatre exhaustively researched and distilled by PJ Paparelli and Joshua Jaeger, directed by Paparelli, and produced by American Theater Company in 2015. We were blown away by the ability of the eight-person ensemble cast to inhabit the many personalities and convey the compelling stories of residents, planners, social workers, and academic researchers, aided immensely by the choreography of Jakari Sherman and the musical direction of Aaron Benham.

Scene from I Sailed with Magellan at Victory Gardens
Scene from I Sailed with Magellan at Victory Gardens

I Sailed with Magellan by Claudia Allen, adapted from the book by Stuart Dybek, produced by Victory Gardens Theater in 2007: This warmly nostalgic coming-of-age play is based on Stuart Dybek’s experiences growing up in Chicago in the 1950s and 60s. Rather than a chronological narrative, the play consists of a series of disjointed vignettes going back and forth in time, recalling both pleasant and bittersweet memories. The outstanding cast was led by Bubba Weiler as young Perry, Marc Grapey as his father, and Lance Baker as his alcoholic jazz musician uncle. The play is rich in Chicago lore of the period and provides fascinating insights into the shaping of a writer. The story of how we unexpectedly came to see this show is recounted in our list of surprises.

Scene from Blizzard '67 at Chicago Dramatists
Scene from Blizzard ’67 at Chicago Dramatists (photo by Jeff Pines)

Blizzard ’67 by John Steinhagen directed by Russ Tutterow produced by Chicago Dramatists in 2012: No discussion of Chicago would be complete without mentioning its weather, which was a major adjustment for us when we moved from Tennessee. Although Chicago winters are not uniquely unpleasant, it often seems that way to its inhabitants. Our favorite theatrical riff on this theme takes place during Chicago’s infamous blizzard of 1967, as four average corporate Joes attempt to drive home from their downtown workplace despite the impassible conditions. Though mostly hilariously comical, their conversations and exploits also have a serious side, as the normally competitive protagonists must cooperate to succeed in their perilous journey home. The intimacy of the venue and the simplicity of the set—four chairs simulating a car plus a rear screen for projections of snow, lots of snow—contributed to the effectiveness of this highly verbal comedy.

Scene from Blizzard '67 at 16th Street Theatre
Scene from Blizzard ’67 at 16th Street Theatre (photo by Anthony Aicardi)

In 2017, the 50th anniversary of the legendary blizzard, we saw 16th Street Theatre’s dynamic production of the play, directed by Ann Filmer, with actor Stephen Spencer and scenic designer Grant Sabin from the original Chicago Dramatists production. This wonderful theatrical experience was further enhanced by the lobby display, with 1967 newspaper photos of the blizzard and numerous handwritten reminiscences by audience members. Ironically, one contributor, a Sun-Times photographer, noted that his photo editor on the fateful day had told him not to turn in any “snow photos,” saying that “When our next issues come out a week from today, nobody will even remember it snowed.”

Megan Kohl and Chaon Cross in Proof at Court Theatre
Megan Kohl and Chaon Cross in Proof at Court Theatre (photo by Michael Brosilow)
Charles Newell interviewing playwright David Auburn at the Logan Center; Michael and Mona are in the audience
Charles Newell interviewing playwright David Auburn at the Logan Center, with Michael and Mona in the audience (photo by Robert Kozloff)

Proof by David Auburn: Perhaps it’s due to our own mathematical backgrounds, but our favorite theatrical example of intellectual life in Chicago is David Auburn’s Proof, about Robert, a mathematician at the University of Chicago whose struggle with mental illness has critical repercussions for his daughter Catherine, whose own budding mathematical education has been interrupted in order to care for him. We have seen numerous fine productions of this play in St. Louis, Indianapolis, Milwaukee, Urbana, and Washington DC, plus several more in Chicago. But perhaps the most meaningful and memorable productions both took place, appropriately, on the University of Chicago campus in Hyde Park. First was an outstanding UC production celebrating the opening of the new Logan Center in 2012, directed by Audrey Francis and featuring Steve Pickering as Robert and UC student actors in the other three roles. A highlight of this event was a public interview with playwright Auburn conducted by Charles Newell, artistic director of UC’s Court Theatre, where he would be directing a professional production of Proof a few months later. We’ll never forget Auburn’s reaction when Newell asked him whether the set has to be a back porch (as called for in the stage directions and as in every other production ever mounted). When we attended Court’s subsequent production, we were not surprised to see that the back porch had been abstracted beyond recognition! The superb cast included Kevin Gudahl as Robert, Chaon Cross as Catherine, Megan Kohl as her sister Claire, and Erik Hellman as Robert’s graduate student Hal. And in a magnificent touch, the three student actors from the earlier production served as understudies for the Court production.

Stef Tovar in A Twist of Water at Route 66
Stef Tovar in A Twist of Water at Route 66 (photo by Brandon Dahlquist)

A Twist of Water by Caitlin Montanye Parrish, directed by Erica Weiss, produced by Route 66 Theatre Company in 2011: Chicago has an intimate and longstanding relationship with the two dominant bodies of water that help define it, Lake Michigan and the Chicago River. In this play, episodes in that history are layered on top of an intimate, nontraditional family drama involving loss and disconnection, but ultimately hope. The play is unified by the metaphorical connections between changing the course of a river and changing course in life. A very strong cast, led by Stef Tovar as the grieving father and the narrator of the historical asides, brought out both the pathos and the humor of the script in equal measure. Whether considered as an interesting history lesson (illustrated by Jon Boesche’s beautiful projections) or a touching drama, this play gave us more than expected.

Scene from My Kind of Town at Timeline Theatre
Scene from My Kind of Town at Timeline Theatre (photo by Lara Goetsch)

My Kind of Town by John Conroy, directed by Nick Bowling, produced by TimeLine Theatre Company in 2012: First-time playwright Conroy is an investigative journalist who managed to condense nearly 20 years of reporting on corruption in the Chicago Police Department into a gripping ten-character drama. The personalized story focuses on a fictional (but representative) death row inmate, Otha Jeffries, who claims that his confession was extracted through police torture, along with the aggressive police detective responsible for his interrogation. By presenting both sides, as well as making it clear that Jeffries is a menace to society even if he did not commit the particular crime in question, the play lets the audience decide whether justice is being served. Searing lead performances by Charles Gardner as Jeffries and David Parkes as the detective, along with a strong supporting cast and incisive direction by Nick Bowling superbly conveyed the moral complexity and dramatic tension of this important story.

The no-frills set of A Steady Rain at Chicago Dramatists
The no-frills set of A Steady Rain at Chicago Dramatists (photo by Jeff Pines)

A Steady Rain by Keith Huff, directed by Russ Tutterow, produced by Chicago Dramatists in 2007: This gritty and absorbing tale of two longtime friends and partners as beat cops on the mean streets of Chicago is mostly told in separate but interwoven narratives from their individual perspectives. What starts out as a diverting buddy story turns into a harrowing drama of violence, tragedy, and betrayal. Randy Steinmeyer and Peter DeFaria seemed utterly authentic and believable as Chicago cops spitting out Huff’s tough, streetwise dialogue. Once again we were amazed by what Chicago actors can convey while simply sitting at a table in a dingy police station. The production was a huge hit and went on to an extended run at the much larger Royal George Theatre, as well as a remount with the original cast back at Chicago Dramatists in 2012. We also saw very credible productions at the Station Theatre in Urbana in 2010 and at the Repertory Theatre of St. Louis in 2012. The play also had a successful Broadway production in 2009 starring Hugh Jackman and Daniel Craig.

Scene from Exit Strategy at Jackalope Theatre Company
Scene from Exit Strategy (photo by Ryan Bourque)
Cast of Principal Principle
Cast of Principal Principle (photo by Emily Schwartz)

Principal Principle by Joe Zarrow, directed by Scott Bishop, co-produced by Theatre Seven and StageLeft Theatre in 2014Exit Strategy by Ike Holter, directed by Gus Menary, produced by Jackalope Theatre Company in 2014: We got a glimpse of life in the trenches for the beleaguered teachers in Chicago Public Schools in not one, but two timely and remarkably affecting plays in 2014. In Principal Principle by Joe Zarrow (himself a former CPS teacher), we see how standardized tests and the rigidly mandated curricula that go with them—not to mention a general lack of resources—sap the initiative and spirit of even the most dedicated teachers, from idealistic novices to jaded veterans. As its title suggests, playwright Ike Holter’s Exit Strategy concerns a CPS high school scheduled for closing at the end of the school year, another au courant hot-button issue for Chicago schools. The two productions had a lot in common besides CPS: both casts were diverse and deeply committed, both plays are tightly focused on teachers and administrators (as opposed to students), neither takes place in the classroom (one in the teachers’ shared office, the other in a dingy teachers’ lounge), both feature realistic and compelling dialogue, and neither posits any easy solutions. One difference is that while Zarrow set out to write a play about CPS, Holter has said that he simply wanted to write about people striving on against the odds and a school closing happened to fit perfectly. These plays should be required viewing for everyone concerned with CPS, including elected officials, but when we attended the audiences were filled with CPS teachers reacting vocally to the action on stage with cries of recognition and (at least figurative) shouts of “amen.”

Sydney Charles and Julian Parker in Jackalope's Prowess
Sydney Charles and Julian Parker in Jackalope’s Prowess (photo by Joel Maisonet)

Prowess by Ike Holter, directed by Marti Lyons, produced by Jackalope Theatre Company in 2016: How far would you go in defending yourself in a dangerous world, and where is the line between self-defense and vigilante justice? These are among the many searching questions raised by this hyperkinetic thrill-ride about four victims or potential victims of Chicago street violence who band together to learn and practice self-defense, and perhaps a bit of revenge. The rapid-fire dialogue was witty and the faux super-hero motif was cool, but the most notable aspect of the production was the Jeff-Award-winning fight choreography by Ryan Bourque, which accounted for a substantial portion of the running time, and the skill and verve with which it was executed by the breathtakingly game cast, Sydney Charles (previously known mainly for musicals), U of Illinois alums Julian Parker and Donovan Diaz, and late replacement Andrew Goetten, whose performance earned a place on our favorite understudy performances list.


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