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When Andre de Shields was nominated on May 5, 1997, for the Tony Award for Best Featured Actor in a Musical for his work in “Play On!,” an updating of Shakespeare’s “Twelfth Night” to a score of Duke Ellington standards, the former Chicagoan did not have very long to savor his moment of Broadway glory. Hours later, the producers of the musical told the cast that the show would be closing on the next Sunday, after just 61 performances and several weeks of playing to little more than half the capacity of the 1,080-seat Broadhurst Theatre. A failure to receive a Tony nomination for Best Musical had put the nail in the show’s Broadway coffin.

In the following weeks, the news got even worse. Not only did De Shields leave the Tonys empty handed, but also a “definite” London opening date turned out to be bogus when one of the principal investors for the planned production at the Savoy Theatre pulled his funding. The expected fall move of “Play On!” to the West End (generally a hospitable home for shows based on American jazz) never happened.

But just one year after all this New York unpleasantness, “Play On!” is being remounted, at the Goodman Theatre (opening night is Monday), with most of its original creative team still in place and determined that their work should get a second hearing in a more hospitable setting. And not only is this production moving to the Seattle Rep after its summer Chicago sojourn, but a national tour also will emanate from the Goodman’s version (New York is not on the list of destinations).

So why did this seemingly popular show fail on Broadway? And will things be different this time around?

Like most folks who have been burned in Manhattan, director Sheldon Epps points out the institutional forces that worked against “Play On!” on Broadway last year. For one thing, the show was produced (relatively) cheaply, and it did not come with a star name attached. Ellington’s fame, it seems, was not enough.

“We opened right at the end of the season in a glut of other shows,” Epps reflects. “We were lost amidst the eight musicals all starting in one month. Without the funding of a huge corporation behind us to help us get attention, it was easy to be overshadowed.”

Epps’ conception also was burdened by comparisons with a previous theatrical piece based on Ellington’s music, “Sophisticated Ladies.”

“That was a revue and we are a book musical,” says Epps. “The songs here are all used in such a way that they advance both plot and character. Ellington’s legacy deserves that kind of treatment.”

Some Broadway observers think a big mistake was made when “Play On!” chose to bypass the Shubert Theatre, where it was originally scheduled for a Chicago tryout in early 1997. Had the show been well received here, it would have gained the imprimatur of a major theater city and not gone to Broadway directly from a non-profit house. But that would have cost a lot of money, and the undercapitalized show gambled instead on rave New York reviews.

Such a response never came. Although critics could hardly quibble about the quality of such compositions as Billy Strayhorn’s “Take the A Train” and Ellington’s “It Don’t Mean a Thing If It Ain’t Got That Swing,” and many reviews praised the choreography by Mercedes Ellington (granddaughter of Duke) and the lush orchestrations, there were mutterings that the book was thin and the production values less than stellar. More significantly, many reviewers took offense at the broad — some called it “stereotypical” — performance style that was intended to reflect that of African-American entertainers who worked at venues like The Cotton Club of Harlem in the 1920s and early 1930s (a venue that featured black performers singing for exclusively white audiences).

The criticism that the show perpetuated racial stereotypes irritates both Epps and De Shields to this day.

“I would never change that performance style,” says Epps. “It’s an homage to a vital period in the history of black entertainment. And we reserve the right as black performers to have as much fun as anyone else.”

“I’ve had it up the eyeballs with that double standard,” says De Shields. “Stereotypes are the essence of Broadway, yet those paternalistic white critics patronized our show. They had no idea where I was coming from, yet they sat in judgment of my intent. . . .”

This version of “Play On!” features some revisions (although it’s much the same show). Epps says that a fairly long scene from the first act has been excised. Some of the dance sections have been edited. Writer Cheryl L. West has made some small adjustments to the script. And the lack of a fly system at the Goodman meant that the design scheme had to be rethought, engendering what Epps and De Shields see as significant improvements in the look of the piece.

“I’m doing this again because I love to be back in Chicago and I like working with these people,” says De Shields. “I think `Play On!’ deserves to be considered as a significant contribution to the Afrocentric canon of literature. And besides, we never got the chance to finish experimenting.”

When West, a former resident of Champaign, Ill., showed up as the book writer for “Play On!,” some of his admirers were relieved to discover that this talented scribe was still working. A playwright with a long history of productions in Chicago, West wrote “Jar the Floor” (produced here by the Northlight Theatre) and “Puddin’ and Pete” (Goodman Studio), but it has been some time since this once-prolific author was attached to a major new play. West’s best and most recent drama, “Holiday Heart” (about a drag queen who rescues a little girl from the ghetto), has still never been seen in Chicago after a negative critical response to a New York production.

“I’m working on a new play about race for the Manhattan Theatre Club,” West said by telephone from the East Coast.

“I’ve never been championed in New York,” West says, “but all of the national productions of `Jar the Floor’ are still paying my mortgage.”