Special Reports

7 Stars You Didn't Expect to See in Broadway's Chicago

What do the likes of Sofia Vergara and Usher have in common?

Throughout its 18-year run on Broadway, Walter Bobbie's Tony-winning revival of Chicago has welcomed a host of performers to take on the principal roles of Roxie Hart, Billy Flynn, and Matron "Mama" Morton. Some of the choices were not unexpected, like John O'Hurley (of TV's Seinfeld and Dancing With the Stars). Others, like Melanie Griffith as Roxie Hart, were far more surprising. In that vein, on the occasion of Chicago's record-breaking 7,486th performance, we decided to look back on some of the more unexpected performers who trod the boards of Broadway in these crucial roles.

Sofia Vergara as Matron "Mama" Morton
Sofia Vergara as Matron "Mama" Morton.

1. Sofia Vergara

Best known for playing Gloria Pritchett on Modern Family, Vergara took on the role of Matron "Mama" Morton from April to June in 2009, shortly before the hit ABC sitcom premiered.

Jerry Springer as Billy Flynn
Jerry Springer as Billy Flynn.

2. Jerry Springer

The tabloid talk-show host played rascal lawyer Billy Flynn in August and September of 2009. The engagement marked his second Broadway appearance; the first was a weeklong run as the Narrator in the 2001 revival of The Rocky Horror Show.

Wendy Williams as Matron "Mama" Morton
Wendy Williams as Matron "Mama" Morton.
(© Jeremy Daniel)

3. Wendy Williams

The comedian and talk-show host played a two-month 2013 engagement as Matron "Mama" Morton and managed to work her signature catchphrase, "How You Doin'?," into her dialogue.

Billy Ray Cyrus as Billy Flynn
Billy Ray Cyrus as Billy Flynn.

4. Billy Ray Cyrus
The "Achy Breaky Heart" singer played a holiday-season run as Billy Flynn in 2012 and helped the show mark its 6,681st performance.

Ashlee Simpson as Roxie Hart
Ashlee Simpson as Roxie Hart.

5. Ashlee Simpson

Years after her Saturday Night Live lip-synching debacle, the "Pieces of Me" singer played Roxie Hart from the 2009 holiday season into early 2010.

Usher as Billy Flynn
Usher as Billy Flynn.
(© Paul Kolnik)

6. Usher Raymond

The hunky R&B singer made his stage debut as Billy Flynn, from August 22-October 6, 2006, but was forced to leave the show earlier than expected following a bout with strep throat.

Christie Brinkley as Roxie Hart
Christie Brinkley as Roxie Hart.
(© David Gordon)

7. Christie Brinkley

The statuesque supermodel played two engagements in the musical, in 2011 and 2012, and helped the show celebrate its 6,000th Broadway performance.

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