Chicago Turns 22! Check Out the Stars Who Have Played the Longest Runs as Roxie, Velma, Billy, & More

Last updated November 14th, 2018 by Josh Ferri
Chicago Turns 22! Check Out the Stars Who Have Played the L…

The Tony-winning, record-breaking revival of Chicago

opened on Broadway 22 years ago on November 14. To celebrate the iconic New York institution, we spotlight the actors who have starred in the leading roles the longest.

Charlotte d’Amboise as Roxie Hart


The Tony-nominee has played foxy Roxie Hart for over 2,135 shows! (Her song begins at 7:10.) All together there have been 46 actresses who have played the jilted killer over the 22 years.

Amra-Faye Wright as Velma Kelly


The South African star is Broadway’s current Velma, and she’s taken the stand and cell block tangoed for over 2,700 shows. Chicago remains her sole Broadway credit, and she’s also played the role on tour and internationally. There have been 34 Velmas over the past two decades.

Brent Barrett as Billy Flynn


The dashing Brent Barrett has played the slick Windy City lawyer for over 1,830 shows between 2003 and 2014. A total of 63 actors have razzle dazzled as Billy since opening night.

Raymond Bokhour as Amos Hart

Raymond Bokhour-Amos-Chicago Broadway Musical
Photo by Jeremy Daniel

The actor, writer, and composer has been Roxie’s funny honey for over 2,828 performances. He’s one of only 24 actors to sing “Mr. Cellophane” in this production.

Roz Ryan as Matron “Mama” Morton

When you’re good to Roz Ryan, she’ll remain the countess of the clink for over 2,300 shows. She’s one of 35 actors to spice it up as Mama.

R. Lowe as Mary Sunshine

The current Mary Sunshine has been spreading a little bit of good for over 5,499 performances—making Ryan the longest running principal in the musical. A very select club of only 15 actors have played the role in the 22 years.

Donna Marie Asbury & Brian O'Brien

Donna Marie Asbury Gif- Chicago GIF- Cell Block Tango GIF- He Ran Into My Knife GIF

Donna Marie and Brian are Chicago mainstays, both having danced the Fosse musical for years and years. Donna Marie plays June ("you've been screwing the milkman") and understudies Velma & Mama. Brian kicks off the musical as the short-lived Fred Casely and understudies both Billy & Amos.

Check out ‘Chicago’ at Broadway’s Ambassador Theatre.