31 Jeremy Wechsler
Artistic director, Theater Wit
File this one under showbiz-sized cojones. Until a year or so ago, Wechsler’s Theater Wit was a small company, best known for its annual holiday production of David Sedaris’ “Santaland Diaries.” Then, Bailiwick Repertory imploded and gave up its theater complex on Belmont in Lakeview. Wechsler took over the property, raised money and convinced esteemed local theater companies, some already renting their own homes, some “gypsy,” to join him in a beautiful new space tailor-made for mid-sized shows. Folks scratched their heads at Wechsler’s ambition, but he pulled it off, and added a terrific new venue to the city’s relatively meager stock of Class A theaters available to produce small-to-mid-sized shows.
32 Rachel Kraft
Executive director, Lookingglass Theatre Company
Running a multimillion dollar theater operation is no small feat under any circumstance, but it’s especially challenging for Goodman vet Rachel Kraft, now in her sixth year at the Lookingglass helm. Not only is she faced with the challenges (and benefits) of operating out of the more-than-a-century-old Water Tower Water Works on Michigan Avenue, but she works with an artistic director that rotates among ensemble members, meaning she has little leadership continuity in that role to lean on. And, since Lookingglass produces shows with a dance-like physicality, she’s implemented a program of repertory revivals of many of their most popular creations, putting the onus on single-ticket sales rather than subscriptions.
33 Russ Tutterow
Artistic director, Chicago Dramatists
After twenty-five years as artistic director, Russ Tutterow is synonymous with Chicago Dramatists, an organization synonymous with the nurturing of playwrights. Make a list of Chicago’s top theatrical scribes and it’s likely most if not all will be one of forty residents at Chicago Dramatists. Some, like Keith Huff, Rick Cleveland and Tina Fey, might even make a few lists outside of Chicago. A tireless champion of his company’s mission, Tutterow’s a seeming around-the-clock presence, presiding over the weekly Saturday readings of works in progress and personally welcoming each new class of students who come to study the writer’s art and perhaps become the next resident playwright. And he still finds time to direct at least one show a year, helming “Hickorydickory,” a new play by Marisa Wegrzyn, in May.
34 Brian Dickie
General director, Chicago Opera Theater
Brian Dickie’s surprise announcement that he was stepping down next year after ten years at the helm of COT was a sobering reminder of just how vital a presence he is in Chicago by imagining just how dull the area opera scene will be without him. Yes, it helps that Lyric is as conservative as COT is innovative, but Dickie has an unparalleled nose for repertoire, singers, directors and conductors, and in fact, virtually handed Music of the Baroque its music director Jane Glover on a silver platter by bringing her here first. And let’s not forget composer John Adams being so thrilled with COT’s “Nixon in China” that he conducted his latest opera not at Lyric, but at COT.
35 Charna Halpern
Co-founder and owner, iO
There’s something sorta old-school about iO and that’s probably because it’s still under the hands-on leadership of its co-founder and owner, Charna Halpern. It’s so well-known as a teaching center for improv—its alumni list is the companion who’s who to The Second City, including Mike Myers, Amy Poehler and Andy Richter—that it’s easy to forget that it’s also a repertory theater of comedy at its finest, whether it’s the long-running sensation “TJ & Dave” or “SNL” alum Nora Dunn’s one-woman show, running this month.
36 Jan Kallish
Executive director, Victory Gardens Theater
You wouldn’t want to be in Jan Kallish’s shoes right now unless you really love a challenge. After the husband-wife team of Dennis Zacek and Marcelle McVay (artistic and managing director, respectively) built Victory Gardens over three decades into Chicago’s new-play treasure, picking up a Regional Tony Award in the process, alleged run-ins with the board over the disposition of its old theater in the wake of its move into the Biograph led to McVay’s departure in 2008. Zacek’s now retiring and the board decided to conduct a national search for his replacement rather than simply giving it to the home-team-and-hometown favorite, the accomplished Sandy Shinner, so Kallish might have to manage quite the fallout if Shinner’s passed over and Zacek’s gone. But existential crisis is what leaders feed on, and Kallish has fought her share of battles, both as a Broadway producer (including “The Color Purple”) and as the executive director of the Auditorium Theatre for six years, where she was in the middle of a battle for control of the theater between its board and its owner, Roosevelt University. If anyone can move Victory Gardens safely through this time of tribulation, the well-regarded Kallish is a very good bet.
37 Kyle DeSantis
Executive producer, Drury Lane Productions
When two generations of the DeSantis leadership passed away within a short time of one another, the Drury Lane empire fell to Kyle DeSantis before he was even 30 years old. Slowly, but surely, DeSantis began beefing up production values and expanding the classic, family-friendly musical theater repertoire long associated with the venue to more contemporary shows and even tried bringing those same shows to Drury Lane Water Tower Place. When it became obvious that DeSantis could not beat Broadway In Chicago at its own game, he threw in the towel and shrewdly sold the downtown venue to BIC, putting all of his eggs in the basket of what is now the single Drury Lane Theatre in Oakbrook Terrace. DeSantis has realized that if you concentrate on making the productions of the suburban Drury Lane second to none in quality for a bargain price, even city theater lovers will gladly flock to the party.
38 Lane Alexander
Co-founder and director, Chicago Human Rhythm Project
The founder of the Chicago Human Rhythm Project has not only inspired a generation of tappers, he has made Chicago an international destination for the percussive arts. The Rhythm World festival, which celebrated its twentieth anniversary last year, amasses dancers, drummers, beatboxers—anyone who pounds out an artful rhythm—from around the world for a two-week summit of instruction, performing, jamming and bonding. Every art form should have this.
39 Peter Taub
Director of performance programs, Museum of Contemporary Art
It takes guts to present a seven-hour live reading/enactment of “The Great Gatsby,” and Peter Taub did just that in 2008. The house was packed and those lucky enough to catch Gatz were treated to a perspective-altering experience. When the show finally hit New York in 2010, it was the talk of the town, but Chicagoans had already beentheredonethat, thanks to the MCA. Taub’s programming consists of the most interesting new work in dance, theater, music and all imaginable combinations thereof from around the globe.
40 Gary Griffin
Whether it is directing a musical on Broadway or at a local venue, Griffin brings the same integrity and intensity to whatever projects he becomes involved in, always refreshing the works that he tackles. At a time in his career when many directors would rest on their laurels or settle into a niche, Griffin is always expanding, always growing. Just a few days into the new year Griffin revealed his first-ever full-length Shakespeare at Chicago Shakespeare Theater (“As You Like It”) while his magnificent take on “The Mikado” is still across town at Lyric Opera, where he debuted only last year.