(Note: We also have a list of memorable non-Sondheim musicals.)
Stephen Sondheim is at the top of our list of favorite composers and lyricists. We’ve traveled great distances (once in an ice storm) to see productions of his works. Often, a Sondheim production is what prompts us to try a new theatre, whether in Chicago or some other major U.S. city. For example, in 2002 we made our first theatre trip to Washington, D.C., for the Kennedy Center’s six-play celebration of Sondheim’s 70th birthday (Company, A Little Night Music, Merrily We Roll Along, Passion, Sunday in the Park with George, and Sweeney Todd). Sondheim productions also account for our first theatre experiences in Chicago (A Little Night Music at Goodman in 1994); Milwaukee (A Little Night Music at Skylight in 1995); Indianapolis (A Little Night Music at Edyvean, Merrily We Roll Along at Footlite, and Company at Phoenix, all in the same weekend in 1998); and St. Louis (Into the Woods at St. Louis Rep in 1999).
We always look forward with a special sense of anticipation to our next Sondheim show, and enjoy reminiscing about previous experiences. So for other Sondheim enthusiasts, we offer our list of favorite productions of each of his shows.
(in the order in which the musicals were written; the number following the title indicates how many productions we’ve seen of that show)
Quick links: Saturday Night West Side Story Gypsy Forum Anyone Can Whistle Do I Hear a Waltz Company Follies Night Music Frogs Pacific Overtures Sweeney Todd Merrily We Roll Along Sunday in the Park Into the Woods Assassins Passion Road Show Revues and Anthologies
Saturday Night (2)
Saturday Night was Stephen Sondheim’s first professional score, written in 1955, but was not produced at the time because the producer died suddenly at the age of 40. The two productions of Saturday Night we’ve seen are tied for most memorable, but for very different reasons! The first was the inaugural U.S. production, presented by Pegasus Players in 1999, directed by Gary Griffin, with music direction by Thomas Murray and choreography by Marc Robin. Sondheim actually wrote two new songs for this American premiere, while paring an hour off the London production’s three-hour running time. (An interesting side note: Recently, while looking at the program from this production, we noticed that Philip Dawkins was in the cast. His bio noted that he was a freshman at Loyola, but failed to mention that he would become a fabulous playwright—one of our favorites!). Incidentally, the New York Times review of the production, while not totally favorable, had kind words for Philip’s performance: “Philip Dawkins brings polish and an old-fashioned show-biz spirit to his solo number Exhibit A.”
We subsequently saw Saturday Night in Milwaukee in 2003 by Boulevard Ensemble (a small scrappy company with a knack for memorable productions of infrequently performed plays). They had planned to do a full production, but ran out of money for costumes and set. Rather than cancel the show, they charged ahead in street clothes and with handmade cardboard signs indicating what the set would have depicted. Thanks to the extremely talented cast and a fully supportive audience, the performance delightfully captured the spirit of the material.
West Side Story (7)
This landmark masterpiece combines a number of striking elements—athletic and balletic dance, Leonard Bernstein’s poetic and symphonic music, Sondheim’s innovative and clever lyrics, and a Shakespearean plot—to tell a distressingly timeless story of doomed love amid clan (now gang) warfare. The best productions manage to harness all of these diverse elements to form a coherent whole. Perhaps because of the huge demands of the piece, we’ve had the opportunity to see relatively few productions. Here’s what stood out in our favorites:
Stratford Festival in 2009: Directed by Gary Griffin and starring Chilina Kennedy and Paul Nolan, this was by far the most athletic, go-for-broke dancing we had seen at the time—in any musical, not just West Side Story. Choreographer Sergio Trujillo brilliantly adapted Jerome Robbins’s choreography for the thrust stage of Stratford’s 1,800-seat Festival Theatre.
Drury Lane Oakbrook in 2015: Directed by Rachel Rockwell and choreographed/associate directed by Rhett Guter, this production was very different stylistically from Stratford, but equally affecting. The actors playing the two lead couples presented an unusually
introspective, foreboding reading of the characters. The dancing, which had its athletic moments, was thought-provoking and polished, exemplified by Bernardo as played by Lucas Segovia, a member of the Joffrey Ballet (and a fine actor). Overall, the production demonstrated that there are different ways to convey the depth of this beautiful and unforgettable show.
Paramount Theatre in 2016:
Director Jim Corti and choreographer William Carlos Angulo took a fresh, clear-eyed look at every element of this classic, shedding years of patina, to create something piercingly relevant to today. As Angulo said, “I hope we can help the audience re-examine the subject matter in the piece: the hate, the anger.” Mission accomplished, thanks to direction, choreography, singing, acting, and staging that captured the uncontrolled passion, energy, and tragedy of the piece. Lead actors Zoe Nadal (Maria), Will Skrip (Tony), Mary Antonini (Anita), and Alexander Aguilar (Bernardo) were spellbinding in this visceral production that seemed to take place in gang-infested Chicago in 2016 rather than gang-infested New York in 1957.
Gypsy (11)
On only two occasions in our theatre-going lives, we’ve seen productions of classic plays that caused us to recalibrate our expectations of the play’s potential to resonate, thrill, and plumb the depths of our souls. The first was Hans Fleischmann’s Glass Menagerie in 2013 (details in our list of definitive productions). The second was Porchlight’s 2018 production of Gypsy with E. Faye Butler as Madame Rose.
The qualities that made this Gypsy a singular experience started with Butler’s characterization of Madame Rose. The usual brashness and toughness were there, to be sure, but so were a hundred deeper layers of a woman who’d experienced rejection, abandonment, vulnerability, uncertainty—and somehow managed to hold on to her dreams. Butler’s exquisite singing was matched by her inspired and meticulous acting.
Similarly, the rest of the cast was spot-on in capturing their characters’ essence. Even the young children in the cast acted with remarkable authenticity and depth. Daryn Whitney Harrell played Louise, surely one of theatre’s most demanding character transformations from an unassuming pre-teen into Gypsy Rose Lee. We had never seen this role played so believably throughout every scene. In the crucial and very tricky role of Herbie, José Antonio García heartbreakingly captured his character’s ambivalence between hope and resignation.
Porchlight’s beautifully sung production was music directed by David Fiorello, who re-orchestrated the score for seven musicians—easily the fullest sound we’d ever heard from a septet. We’d also never heard a music theatre orchestra sound so different depending on the demands of the scene, whether playing for Uncle Jocko’s kiddie show, the “You Gotta Get a Gimmick” strippers, or the climactic “Rose’s Turn.” And Gypsy is a musical with a lot of scenes! Director Michael Weber, in collaboration with scenic designer Jeffrey D. Kmiec, was somehow able to use the ingenious set (moved by members of the supporting cast) to pull off complicated set changes in what seemed like milliseconds. And Bill Morey’s costume design was a dream from start to finish.
Prior to Porchlight’s Gypsy in 2018, we had experienced nine previous productions, most of which sank or swam with the casting of Rose and her agent and sometime love interest, Herbie. Fortunately, we have seen a number of remarkable actresses successfully embody Rose, including Paula Scrofano (Theatre at the Center 2003), Rebecca Finnegan (Porchlight 2005), Klea Blackhurst (Drury Lane, 2012), and Louise Pitre (Chicago Shakespeare 2014), and several equally capable Herbies, including David Girolmo (Theatre at the Center 2003), Mick Weber (Porchlight 2005), David Kortemeier (Drury Lane 2012), and Keith Kupferer (Chicago Shakespeare 2014). A relatively minor, yet potentially show-stealing character is Tulsa, a role we have seen played to perfection by Matt Crowle (Drury Lane 2012) and Rhett Guter (Chicago Shakespeare 2014). Oddly, the roles of the two daughters on whom Rose lavishes her attention, June and Louise, have tended to be less crucial and less memorable, at least to us, possibly because they were simply overshadowed by Rose.
Special mention should be made of the production of Gypsy at the Shaw Festival in 2005, in which Nora McLellan was cast as Rose, but in the performance we saw we happened to catch her alternate, Kate Hennig (also a fine playwright), who we thought hit the role out of the park. Ric Reid made an appropriately poignant Herbie, in another of our favorite productions of this classic show.
A Funny Thing Happened on the Way to the Forum (24)
We’ve seen many productions of Forum, but few that have successfully mined all the possibilities in this deceptively difficult piece. Interestingly, our favorite production was in 1999 by the University of Illinois student union (their annual show for “Dad’s Weekend”—theatre for dads who aren’t excited about Illinois football). There were inventive sight gags, great physical comedy from the Proteans, and easily the best staging of “Pretty Little Picture” we’ve ever seen.
Other favorites: The 2005 Marriott Lincolnshire production, with Guy Adkins as Pseudolus and Bernie Yvon as Hysterium; the 2009 Stratford Festival production, with Stephen Ouimette as Hysterium, Chilina Kennedy as Philia, and understudy Randy Ganne as Pseudolus, filling in for the injured Bruce Dow.
Anyone Can Whistle (3)
It’s hard to believe that the same person wrote the books for West Side Story and Anyone Can Whistle, but Arthur Laurents had range. Unfortunately, it wasn’t appreciated by Broadway audiences in 1964, so Anyone Can Whistle famously closed after nine performances. Fortunately, the soundtrack recording and subsequent regional productions have kept the wonderful music and quirky story alive. We deeply regret missing the acclaimed 1989 Pegasus Players production, which won four Jeff Awards, including best production, and featured Larry Yando as Hapgood. (We did see their 2004 production, which was less successful; interestingly, it replaced their originally scheduled show The Frogs in deference to the Lincoln Center production with revised book by Nathan Lane.) We have been fortunate to catch two outstanding productions of Anyone Can Whistle: New Line Theatre in 2001, directed by Scott Miller, and Porchlight Revisits in 2013, directed by Christopher Pazdernik with music direction by Aaron Benham.
Do I Hear a Waltz? (2)
This musical, the only collaboration between Richard Rodgers and Stephen Sondheim, is rarely produced, so we jumped at our only two chances to see it. The production at Theatre at the Center in 2005 featured a dream-team cast, headed by Hollis Resnick, Larry Adams, and Paula Scrofano, directed by William Pullinsi. The musical was beautifully sung and acted, but despite a significantly thrust stage, the several-hundred-seat venue seemed too large for the material. Do I Hear a Waltz? is a decidedly small-scale musical, where it’s crucial for the audience to connect with the characters up close and personal. So we were excited when we had the opportunity nine years later to see the piece in a significantly more intimate space, at Music Theatre Company in Highland Park. With Kelli Harrington and David Girolmo playing the leads, along with a superb supporting cast and direction by Dominic Missimi, the performance was exquisite, and the venue was ideal (a few dozen seats, on the same level as the stage). We thoroughly enjoyed both productions, and the contrast in venue gave us some insight into one of the reasons that this interesting-but-imperfect piece is rarely performed and was not well-suited to Broadway.
Company (18)
Company is a very challenging piece, starting with the central character (Bobby), who is a bit of a cipher emotionally and spends most of the show reacting to those around him rather than setting his own tone. Some actors fall into the trap of treating Bobby’s big second act solo “Being Alive” as a power ballad, with no range of emotions and certainly no trace of vulnerability. Besides a well-acted Bobby, another element that has characterized our favorite productions is superb acting from Amy (the reluctant bride in “Getting Married Today”) and April (the flight attendant who sings “Barcelona” with Bobby). And bonus points for members of the male supporting cast who are able to go beyond wisecracking and build credible characters. Our favorite productions of Company have featured not just excellent music, but top-notch acting as well.
The Pegasus Players production of Company in 1997, our first, was directed by Gary Griffin, with choreography by Marc Robin. The show incorporated a few updates from Sondheim and George Furth. The cast was uniformly excellent, and included always-wonderful Laura T. Fisher as Joanne. Brian Stepanek as Bobby captured every ounce of emotion and self-discovery in his rendition of “Being Alive.” Just three months after the Pegasus production, we saw an excellent Company at Phoenix Theatre in Indianapolis. The Jonathan Berry-directed production by Griffin Theatre in 2010 featured some dynamite performances, including Dana Tretta singing “Another Hundred People” and Darci Nalepa’s rendition of “Getting Married Today.”
In 2016, four years after his resplendent A Little Night Music, director William Brown brought another Sondheim gem to Writers Theatre. Even though we had seen 14 prior productions of Company, we had never seen one where Bobby’s emotional arc was so well motivated, and where the sketches that make up the book were like pieces of a single puzzle that clicked into place as the show progressed. We had always loved the music and lyrics in Company, but had found some parts of the book to be more engaging than others. In the Writers Theatre production, everything was part of the same logical fabric, thanks to the cast of heady actors assembled by Brown and their shared conception. Ironically, in a musical consisting of vignettes, we saw first-rate ensemble work, in addition to solos being knocked out of the park, including “Another Hundred People” (Christine Mild as Marta), “Getting Married Today” (Allison Hendrix as Amy), “The Ladies Who Lunch” (Lia Mortensen as Joanne), and “Being Alive” (Thom Miller as Bobby).
The 2018 Company by Mercury Theater Chicago was one of our favorites and an auspicious first show in Mercury’s new Venus Cabaret Stage. It featured a couple of other firsts for us (even though it was our 17th production of this musical): easily the most intimate venue, as we gleefully sat inches from the actors and basked in the pure unamplified sound; and the first (and undoubtedly only) time the audience was served birthday cake baked by the music director (Eugene Dizon)! Director L. Walter Stearns staged the production very cleverly in the intimate space, with a cast of Chicago favorites whose terrific voices were matched by first-rate acting.
Follies (11)
Our most memorable Sondheim production ever was a concert presentation of Follies in Ann Arbor, Michigan, in January 2003. The concert took place in the 75-year-old Michigan Theater, a classic vaudeville and movie palace that, unlike the Broadway theater in Follies, was lovingly restored after years of neglect. Thirty-two years after the original Broadway production, the 2003 concert reunited the four actors who had played the young versions of the lead characters on Broadway, now playing the older Ben (Kurt Peterson), Phyllis (Virginia Sandifur), Buddy (Harvey Evans), and Sally (Marti Rolph). Their younger versions were played by four marvelously talented University of Michigan students majoring in musical theatre. Broadway veteran Donna McKechnie played Carlotta Campion. The Chair of the University of Michigan Musical Theatre Department, Brent Wagner, directed the production, with music direction by Bradley Bloom and a 39-piece orchestra.
The idea of staging Follies came from the manager of the Michigan Theater, Russ Collins. Reuniting the four actors to play the older versions of their Broadway roles was the brainchild of the theater’s Director of Programs, Emily Phenix. “Young Ben” Kurt Peterson had been her voice teacher, so she contacted him. He enthusiastically agreed to contact the other three actors, all still warm friends decades after their original work together. The two men told long-time acquaintance Donna McKechnie about the planned performance. She is from Michigan, and had already planned to return to celebrate the 75th birthday of her childhood dance teacher and see family during the holidays. So the stars aligned for her to perform in Follies as part of that trip. Needless to say, the show was unbelievably moving and beautiful, and we were still euphoric, even as we drove through an ice storm on our return home to Illinois.
In better weather, we traveled to the Kennedy Center in 2011 to see Bernadette Peters in a marvelous production of Follies, which subsequently transferred to Broadway. Just four months after Kennedy Center, we saw another acclaimed production at Chicago Shakespeare Theatre. We would be remiss if we didn’t also mention the first time we saw Follies: a phenomenally effective production by the University of Illinois student union in 1994. In stark contrast to the $7.3M Kennedy Center production or the lavish Chicago Shakespeare production, the student effort was a great example of how talented students with dedication, ingenuity, and focused collaboration can do justice to one of our favorite Sondheim Shows.
A Little Night Music (22)
As you can tell from our list of Sondheim favorites, we’ve seen many fine productions that had few resources to work with, other than talent, commitment, and imagination. But A Little Night Music is an exception to that rule. All our favorite productions have been handsomely decked out, creating an elegant setting for the often inelegant capriciousness of the play’s characters and relationships.
The first time we saw A Little Night Music was at the Goodman Theatre in 1994. It was not only our first visit to the Goodman, but also our first theatre trip to Chicago. And we saw a classic Goodman production: A-list cast (Paula Scrofano, Hollis Resnik, Ann Whitney, et al), A-list director (Michael Maggio), and elaborate costumes and scenic design (including working cars when characters arrived for the second-act weekend in the country).
In contrast to the decidedly large-scale Goodman production, Writers Theatre in 2012 staged a glorious chamber musical rendition in their cozy 108-seat space. Directed by William Brown (with Valerie Maze as music director and Roberta Duchak as music supervisor), this Night Music personally connected to the audience, with unamplified music and intimate performances. On the first row, we were so close that the actresses’ ball gowns brushed our feet as they waltzed by. Shannon Cochran and Jonathan Weir were born to play Desiree and Fredrik, Tiffany Scott and Brandon Dahlquist captured the humor and complexity of Charlotte and Carl-Magnus, and Brianna Borger (Petra) and Deanna Dunagan (Madame Armfeldt) brought depth to their characters’ versions of “one does what one can.” William Brown wrote in the playbill that he had contacted Michael Halberstam the morning after seeing his production of She Loves Me at Writers, “utterly enchanted” and eager to do Night Music in that same space. We were all the richer for it.
We’ve seen other noteworthy productions that have featured inspired casting choices for various roles in Night Music:
Carl-Magnus: In 1998, a wryly imposing David Girolmo at Theatre at the Center; in 2002, Douglas Sills at the Kennedy Center Sondheim Festival; in 2003, a masterful Michael Cerveris at Chicago Shakespeare Theatre (only a year earlier we had seen him play Giorgio to perfection in Passion at the Kennedy Center)
Desiree and Fredrik: Catherine Lord and Larry Adams at Light Opera Works in 2009; Sylvia McNair and James Rank at Indianapolis Repertory Theatre in 2013
Another perfect Desiree and Fredrik—Colette Todd and Patrick Byrnes—set the tone for Theo Ubique’s 2024 Night Music, directed by L. Walter Stearns. The pair captured the full musical and emotional complexities of Send in the Clowns, in a perfectly calibrated arrangement by music director Eugene Dizon, aided by Linda Madonia. In fact, musicianship (on the part of cast, orchestra, and arrangers) was a hallmark of this production, and a special treat in Theo’s intimate space.
The Frogs (1)
The swimming pool at Truman College in Chicago was the setting for the Pegasus Players 2007 production of The Frogs (using the 2004 book by Nathan Lane, rather than the original Burt Shevelove version). As far as we know, Pegasus has the distinction of being the only theatre company to have produced The Frogs twice; the first time was in 1988, in the same pool as in 2007.
Pacific Overtures (2)
The intimate 2001 production of Pacific Overtures in Chicago Shakespeare Theatre’s upstairs space, directed by Gary Griffin, was staged on a modest wood platform (surrounded by the audience). The minimalist kabuki-style design, movement, and precise rendering of the music and book have made this a production we still talk about over a decade later. After an extended run in Chicago, the production transferred to London’s Donmar Warehouse, where it received an Olivier Award for Best Musical Production.
Sweeney Todd (20)
We’ve seen Sweeney Todd staged with every imaginable type of barber chair, multi-level set, and scenic design from realistic to steampunk. Most of the set designs worked, but few of the barber chairs did. Ultimately, however, this show rests on the talents of the actors and the ability of the director to orchestrate and properly pace the proceedings. Almost all the productions we’ve seen have been quite good (except an extravagantly produced version in which Sweeney Todd’s movements imitated the Hunchback of Notre Dame). Although hard to choose, we’ve highlighted a few that were particularly impressive.
The first time we saw Sweeney Todd was one of the best, a community theatre effort staged at Parkland College in 1994. In addition to a sparkling cast and brilliantly designed set, it featured the most functional and authentic barber chair we’ve ever seen. The production at the Kennedy Center in 2002 was directed by Christopher Ashley and starred Brian Stokes Mitchell and Christine Baranski. Their rendition of A Little Priest was worth the trip from Illinois to D.C., but was only one highlight of an amazing show. Sweeney Todd at the Drury Lane Oakbrook Theatre in 2011 was directed by Rachel Rockwell, and had an ensemble so good that most of its members could have easily stepped into the lead roles. In addition, the remarkable 13-year-old Jonah Rawitz played Toby, the only time we’ve seen that role not played by an actor somewhat older than the character.
Sweeney Todd at the Paramount Theatre in 2017 featured arguably our all-time favorite Sweeney (Paul-Jordan Jansen) and Mrs. Lovett (Bri Sudia), and their scenes together were nothing short of thrilling. The production, directed by Jim Corti, was further distinguished by possibly the best ensemble singing we’ve ever experienced. And as often happens at Paramount, the three-story scenic design (by Jeffrey Kmiec) was a key component of not just the mood-setting but also the story-telling. More than one reviewer chose “hellish” to describe it (e.g., “providing the hellish world of the musical,” “a piece of hellish genius“), and the effect was intensified by Nick Belley and Jesse Klug’s lighting design. Unforgettable!
Later in 2017, we traveled to Milwaukee to see Skylight Music Theatre’s fine production of Sweeney Todd, with Christina Hall playing a sublime Mrs. Lovett opposite Andrew Varela’s appropriately foreboding Sweeney. Directed by Matthew Ozawa, the production also featured a fully functional barber chair (!), Ryan Stajmiger as the perfect Tobias, and outstanding singing by the entire cast.
We saw our most intimate production of Sweeney Todd in 2018 (directed by Fred Anzevino), produced by Theo Ubique in their home of 13 years—the appropriately named No Exit Cafe (and yes, the dinner that accompanied the show included meat pies). The space accommodated only a few dozen seats for audience members, and in many scenes the cast members were intermingled with the audience. The stereo effect was thrilling, and we savored the glorious voices of the amazing cast without amplification. Theo Ubique’s and Paramount’s productions were the best-sung Sweeney Todds we’d ever experienced; ironically, the former was heard by about 50 people at each performance and the latter by approximately 1,900. As always at Theo Ubique, Jeremy Ramey’s music direction was exquisite, and somehow the four-person orchestra captured both the grandeur and nuance of the breathtaking Sondheim score.
In 2022, we saw Kokandy Productions’ unrelenting Sweeney Todd, imaginatively directed by Derek Van Barham with fierce staging in the Chopin Basement and a fully committed cast of exceptional artists. Ryan Stajmiger, who had been so impressive as Tobias five years earlier at Skylight Music Theatre, proved to be equally adept at embodying Anthony (opposite the fabulous Chamaya Moody as Johanna).
We should also mention that while on a business trip to New York City in 2006, Michael was able to see the John Doyle-directed Sweeney Todd on Broadway, starring Patti LuPone and Michael Cerveris. After Michael returned home to Illinois, Mona got to enjoy his description of the landmark show with Patti LuPone playing tuba.
Merrily We Roll Along (16)
Our first time to see Merrily was a community theatre production at Parkland College in 1997. The excellent quality and clarity of this production gave no hint of the challenges presented by this reverse-chronology show about flawed characters. The next three productions we saw brought home the casting and storytelling obstacles that have bedeviled many talented people in tackling this show. Then we saw the revelatory Merrily directed by L. Walter Stearns with music direction by Eugene Dizon by Porchlight Music Theatre in 2000 (our first of over 90 Porchlight shows over the next 24 years, and still counting). It remains one of our favorite Merrily productions, exemplified by Stephen Rader’s beautifully sung and acted portrayal of Charley Kringas. We saw another memorable Charley, courtesy of Raul Esparza, at the Kennedy Center’s Sondheim Festival in 2002, with direction by Christopher Ashley (who also directed the festival’s Sweeney Todd). Emily Skinner’s portrayal of Gussie was another highlight of a production that made all the right choices. In contrast to the Kennedy Center cast of Broadway veterans, most of the actors in Highland Park’s Music Theatre Company in 2011 were in the early stages of their careers, but bursting with talent. In fact, three years after the production, Chicago Tribune critic Chris Jones wrote an article about the show: Looking back at what turned out to be a whopping cast.
In 2018, Porchlight struck again with another great production of Merrily, joining their 2000 version in our mental catalog of cherished Sondheim memories. The 2018 incarnation, directed by Michael Webber and music directed by Aaron Benham, featured an unbeatable trio of leads: Neala Barron, Matt Crowle, and Jim DeSelm. In addition to their musical achievements (and executing Christopher Pazdernik’s musical stagings to perfection), their acting was spot-on. In over a dozen previous productions, we had never seen these characters so convincingly age-appropriate at every point in the roughly two-decade span of the play. And thanks to Porchlight’s one-night-only staged reading of the 1934 Kaufman and Hart play on which the musical is based, we gained new insights into this much-tweaked musical’s own two-decade journey.
Our fifteenth Merrily production, by Blank Theatre in 2023, had a lot in common with the now legendary 2011 production by Music Theatre Company—namely, early-career artists with abundant talent, exuberantly rising to the challenges inherent in Merrily’s book and music. We were struck by the emotional impact of the show, which was conveyed in both music and acting, and enhanced by director Danny Kapinos’s impeccable pacing and the fluid collaboration of main characters and ensemble. At the heart of the show was Aaron Kaplan’s gorgeous music direction. And all this took place on a stage the size of a modest living room, where we were lucky flies-on-the-wall, relishing a very special Sondheim experience.
Interesting note: In 2024, we were thrilled to catch a one-night-only concert performance of Merrily, reuniting the artists from White Horse Theatre Company’s memorable 2004 production. Life indeed imitated art, as the actors (most in their 20’s at the time of the original production) revisited the material with two additional decades of living and learning under their belts, similar to the journey of the characters in the play. Another similarity in the 2004 and 2024 versions of the show was outstanding quality. Notably, the original production garnered six Jeff nominations, including wins for Nick Sula (music direction) and Cassie Slater (actress in a principal role).
Another interesting note: In a 1997 student production of Merrily We Roll Along that we saw at DePaul University, Charley Kringas was played by Eric Slater, now known for his non-musical work at Goodman Theatre, Writers Theatre, Rivendell, and many others.
Sunday in the Park with George (13)
As is true with many Sondheim musicals, Sunday in the Park with George requires that a number of thorny production elements be practically perfect to do justice to the material. The actors playing George and Dot must be fabulous singers who can bring unusually complex characters to life, and the members of the supporting cast must breathe a third dimension into the 2-D characters of the painting. In addition, the scenic design is immeasureably more than just the set on which the action takes place; it’s the reality of the play. Even the best actors can’t overcome an inadequate scenic design for Sunday in the Park with George. And the staging of the tricky second act is another Waterloo waiting to happen. Needless to say, we have infinite admiration for creative teams and actors who tackle this incredible play and pull it off. Almost all the productions we’ve seen have been laudable and deeply moving, with several stand-outs that were positively awe inspiring. Their resources have varied from minuscule to lavish, the venues from basic to state-of-the-art, and the companies from community theatre to professional (non-Equity and Equity).
Edyvean in Indianapolis in 1999: Our first production of Sunday, it was distinguished by outstanding scenic design, costume design, and a richly textured relationship between George and Dot. They also expertly executed the challenging stage direction that accompanies the title song early in Act 1: “The dress opens, and Dot steps out. It closes behind her, but George continues sketching it as if she were still inside.”
Parkland College in 2001: This community theatre production had the most effective scenic design of any Sunday we’ve ever seen. With a phenomenal cast, creative designers, and talented people working out of sheer dedication, this was a deeply affecting show. (Note: This is the same group that had one of the best sets for Sweeney Todd that we’ve ever seen.)
Kennedy Center in 2002: With Melissa Errico and Raul Esparza as Dot and George, this production made you wish the show would never end. We still get choked up thinking about the experience. The production, directed by Eric Schaeffer, included not just exquisite performances, but also some innovative staging. Act 1 opened with Dot demurely bathing in an on-stage bath tub. The Act 2 staging of “Putting It Together” used life-size cardboard replicas of Raul Esparza that simultaneously worked the crowd of potential donors.
Skylight Music Theatre in Milwaukee in 2012: An all-round excellent production, but the standout was the magnetic performance by Sean Allan Krill as George.
Porchlight Music Theatre in 2024: Porchlight tackled the daunting task of creating a concert staging of a musical whose raison d’etre is visual—and succeeded magnificently! Their inspired choice of venue was the recently restored 600-seat Studebaker Theatre in the venerable Fine Arts Building, just a five-minute walk from the Art Institute of Chicago, home of the painting whose imagined backstory is at the heart of this musical. Directed by Michael Weber, the cast consisted of the luminous Kathy Voytko as Dot, Sean Allan Krill as George (in an even deeper portrayal than we saw previously at Skylight), and a who’s who of stellar Chicago musical theatre performers. The large on-stage orchestra, led by music director David Fiorello, played the original 1984 Broadway orchestrations to perfection.
Into the Woods (30)
We’ve seen Into the Woods performed on sets consisting of a couple of stylized tree trunks, in jungle-like labyrinths, and everything in between. One of our favorite productions, performed on a fairly conventional set, was by the Repertory Theatre of St. Louis in 1999. Not only was that our first theatre outing to St. Louis, but it was also the first time we saw Kate Fry (as Cinderella), now one of our favorite actors in Chicago. The production was beautifully directed by Victoria Bussert, who 18 years later directed Lizzie, the phenomenal inaugural production of Firebrand Theatre in Chicago.
The Hypocrites’ 2014 production of Into the Woods (directed by Geoff Button) was a treat for the eyes and ears, with the company’s characteristic inventive design and staging. But what earned this production a place on our favorites list was the depth of the acting. Even though this was the 21st time we’d seen Into the Woods, we had never experienced it with such a depth of emotion, “realness” of characters, and high-stakes story-telling. It was musical theatre with acting worthy of a Tony Kushner play.
Another favorite Into the Woods was a 2015 production at Northwestern University, directed by Scott Weinstein. The singing and acting were flawless, made even more memorable by some inventive design and staging choices.
Our 26th production of Into the Woods, which we saw at Evanston’s Music Theater Works in 2018, was distinguished by a number of dynamite individual performances, including The Baker (Daniel Tatar), Cinderella (Kelly Britt), Jack (Christopher Ratliff), Little Red Ridinghood (Cecilia Iole), and The Witch (Michelle Jasso). The “cherry on top” of their remarkable singing and acting was the imaginative and perfectly executed character-specific movement—from Cinderella’s golden-slipper-induced pratfalls, to Little Red Ridinghood’s unfailingly adolescent-appropriate body language.
Our next Into the Woods was at Writers Theatre in 2019 (just weeks after their revelatory Next to Normal), and it demonstrated one of the great joys of theatre—that even after experiencing this show more than two dozen times, we could still be surprised, moved, and thrilled anew by how this particular director (Gary Griffin) and these actors and musicians chose to bring this play to life. The depiction of many of the characters was unlike any we’d previously experienced. For example, when Cinderella’s Prince (Ryan McBride) delivered the line, “I was raised to be charming, not sincere,” he did it with a degree of apparent introspection that added dimension to the character without sacrificing the humor. Similarly, the relationship between the Baker (Matt Edmonds) and his wife (Brianna Borger) was played so richly that you felt as if you knew them as people, not just fairy-tale characters. The depth of their connection was all the more remarkable since Matt Edmonds was the understudy, who had assumed the role only one day before we saw him. (This wasn’t the first time we’d seen him perform brilliantly in similar circumstances; see the Murder for Two section of our list of favorite understudies for details.) In this beautifully acted production, even Milky White the cow, played by Mary Poole, made a strong emotional connection to the audience every time she came on stage! The acting was matched by equally exquisite singing, accompanied by Music Director Matt Deitchman’s ingenious re-orchestrations for a fabulous three-musician orchestra (conducted by Charlotte Rivard-Hoster on piano).
Following the pandemic’s theatre hiatus, we reconnected with Into the Woods in a major way in 2023, with three productions in just under two months! First was Paramount Theatre with direction by Jim Corti and Trent Stork, where the highlight for us was the exquisitely staged and executed rendition and reprise of Agony by the two princes (played by Devin DeSantis and Alex Syiek). Next up was a brilliant student production at Millikin University (which made our list of favorite college productions), directed by theatre professor Jefferson Farber—who met and befriended Stephen Sondheim during a summer job while still a student himself at Millikin. Just a few days after the Millikin production, we reveled in the “direct from Broadway” touring production at the Nederlander Theatre in Chicago, directed by Lear deBessonet. Before the show began, we were disappointed to see a program addendum noting that Stephanie J. Block would not be performing the Baker’s Wife at our performance. However, Ximone Rose stepped in and played the role exquisitely. (We had loved her portrayal of Cinderella in Writers Theatre’s Into the Woods in 2019; see the photo accompanying the previous paragraph.) Among the countless joys of savoring this production, we have to highlight Gavin Creel’s take on Cinderella’s Prince/Wolf—one of the best performances we’ve ever seen on any stage!
Assassins (16)
Until near the end, Assassins is in some sense a series of mini-plays featuring one or two actors. In the outstanding productions, all of these episodes hit the mark, and the whole is even greater than the sum of its parts. Our favorites include an amateur student production, a couple of storefront professional productions, and a large-scale Equity theatre show. All were consistently excellent and featured many standout performances.
Assassins at Apple Tree Theatre in 1996 was directed by Gary Griffin, and the cast included a number of performers that were new to us at the time but have become favorites: McKinley Carter (Ensemble, Emma Goldman), Anne Gunn (Sara Jane Moore), and Stef Tovar (Leon Czolgosz). Kevin Earley played the Balladeer until late in the run, when he departed to play Curly in Oklahoma at Drury Lane Oakbrook. By the time we saw the show, George Smart (Lee Harvey Oswald) had also assumed the role of the Balladeer.
In 1998, we saw Assassins by the Penny Dreadful Players, a student-run theatre group at the University of Illinois founded in 1992 (and still going strong), in part as an outlet for non-theatre majors. The show was staged in the sanctuary of an on-campus church, with the pews rearranged to approximate a “theatre in the round” experience. With a production budget probably considerably under $25, the acting was fabulous. We still recall the Sam Byck (played by Daniel Tatar), Sara Jane Moore, and Squeaky Fromme scenes especially—among the best we’ve ever seen.
The staging of Assassins by Boxer Rebellion Theatre in 2003, directed by Michael S. Pieper, was in a very small storefront, which only heightened the effect of the story and the performances of the fine cast.
The production at Milwaukee Rep in 2012 was directed by Mark Clements, with Caroline O’Connor as Sara Jane Moore; the previous year she had won a Jeff Award playing Phyllis in Follies at Chicago Shakespeare Theatre. The ensemble included Rep interns Emily Berman, Toni Linn Martin, Tyrone Philips, Bri Sudia, and Mercedes White, who would shortly make their mark in Chicago theatre.
Interesting note: In 2003, we saw a student production of Assassins at DePaul University in which Leon Czolgosz was played by Tarell Alvin McCraney, now a renowned playwright, actor, educator, and Steppenwolf ensemble member.
Passion (5)
One aspect of Passion that has always fascinated us is that the productions we’ve seen have varied so much in focus and point of view (without changing anything in the canonical book and music). For example, the definitive 2002 Kennedy Center Passion (starring Michael Cerveris and directed by Eric Schaeffer) was first and foremost about Giorgio, and you experienced it through his eyes. By contrast, the excellent 2001 production by Porchlight Theatre (directed by L. Walter Stearns), was all about Fosca, played by Marlene Flood in a
Jeff Award-winning performance. Interestingly, the third of our most memorable Passion productions, by Theo Ubique Cabaret Theatre in 2014, seemed a more balanced emotional triangle, with particular scenes bringing Fosca, Clara, or Giorgio’s point of view to the forefront. This version, directed by Fred Anzevino in a space notably smaller than the orchestra pit at Kennedy Center, brought audience members in close contact with every character; interestingly, critical opinion varied as to which character was dominant and most effectively played.
Road Show (2, including its earlier incarnation as Bounce)
The outstanding 2013 production of Road Show at Chicago Shakespeare Theatre came a decade after the premiere production of Bounce we saw at the Goodman Theatre. Road Show struck us as a “less is more” improvement on the original, in terms of plot, cast, orchestra, staging, and design. The distillation, coupled with a soul-touching performance by Michael Aaron Lindner and a stellar ensemble, under the direction of Gary Griffin, was unforgettable.
Revues and Anthologies
Side by Side by Sondheim (5): Wisdom Bridge Theatre’s 1995 production with Margie Gibson (Interesting note: The show was co-directed by Dale Calandra, who played the title role in The Whale by Samuel D. Hunter at Victory Gardens Theatre in 2013.)
Marry Me a Little (1): Seeing any show with Austin Cook as music director is a thrill not to be missed, but make it a Sondheim revue with him as both music director and performer opposite the sublime Bethany Thomas, and you’ll get to experience musical theatre nirvana. As if that weren’t enough, in Porchlight Music Theatre’s 2017 production of Marry Me a Little, director Jess McLeod’s innovative staging and cohesive direction made this the most seamless revue we’d ever seen. And instead of the usual piano-only accompaniment, Cook’s onstage piano was augmented by an off-stage combo of piano, percussion, cello, flute, and clarinet (playing Cook’s new orchestrations).
Putting It Together (4): Court Theatre’s 1997 production (our first show at Court), with Paula Scrofano, John Reeger, Kevin Gudahl, Kurt Johns, and Kathy Voytko, directed by Gary Griffin; Porchlight Music Theatre’s 2011 production, directed by Brenda Didier with music direction by Austin Cook
Sondheim on Sondheim (1): Porchlight Music Theatre’s 2015 production, with direction by Nick Bowling and music direction by Austin Cook—an impeccable and deeply moving theatre experience
Sondheim Tribute Revue (1): Theo Ubique’s transcendent 2024 Sondheim retrospective was described on their website as follows: “… with special permission from Music Theatre International, Artistic Director Fred Anzevino will helm a one-of-a-kind tribute evening, created especially for our audiences—this production will never be seen again anywhere else!” The uniqueness of the production was further enhanced by special arrangements (by Music Director Carolyn Brady, with contributions from Assistant Music Director Evelyn Ryan), and just-the-right-amount of sassy choreography (by J Alan and Jenna Schoppe)—all performed by a dream cast that got to the very heart of every single musical number. During the show, the musicians and actors each shared a brief personal statement on their own relationship to Sondheim’s work. They were all endearing, heartfelt, and often deeply personal and life-affirming. The bottom line: our favorite Sondheim revue! (To check out the work of two remarkable swings who went on late in the run of this production, see our Favorite Understudies page.)
