Five singers who went from Billboard to Broadway with ease

These singers killed it on stage.
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Usher had recently released his fifth album – Confessions – when he accepted the role of slick lawyer Billy Flynn in the successful revival of Chicago in 2006. Now, there are two ways to look at that. One is that he was flying so high that he could afford to take a chance on something. The other – which I suspect many agents would argue – is that stepping onto a Broadway stage could result in a calamitous fall from grace. But Usher wanted the challenge. He said he had always admired the talent and dedication of Broadway actors, and he wanted to be a part of it.

Billy Flynn is a role that lends itself to a showman. If you can sing, all the better. But a massive voice isn’t the first requirement. Richard Gere played the role in the film version. James Naughton and George Hamilton had done it as well. Nice voices, but not ones that knock your socks off. Then again, it had also been performed by Huey Lewis, and later Miley’s dad Billy Ray would take it on. So it’s not like a singer couldn’t handle it.

As it turns out, Usher brought something that many of the other stars who played the role couldn’t match. He could sing just fine, and his acting suited the blustery attorney well enough. But Usher, primarily through his dancing and movement, showed off the slinky sex appeal that made Billy a different kind of character. Chicago may not have needed Usher.

The show had opened ten years earlier to massive plaudits. It was still going strong when he arrived and continued long after he left. And Usher didn’t exactly need Chicago. Though he would never hit the stratosphere the way Confessions did in 2004, the three albums he released in the five years after his Broadway turn, all reached number one. Still, it’s nice the show and the performers found each other for a little while.


We’ve mentioned a bunch of recording artists who took roles in Broadway shows. We have not mentioned a different set of recording artists who have written the music or lyrics for Broadway shows. Sara Bareilles did both. In 2013, she began writing music and lyrics for a new musical, which would be based on the Adrienne Shelly film of the same name. Three years later, it opened on Broadway.

But Bareilles wasn’t acting in it at that point. Jessie Mueller, coming off her Tony-winning role as Carole King in Beautiful, was cast in the lead. Mueller was again nominated for a Tony for her work in Waitress. But long-running shows often have to replace cast members, and a year later, when Mueller left the production, Bareilles stepped onto the stage as the lead in her own show.  The show ran for three more years (with several other actresses taking over the lead) before Bareilles starred in a limited-run revival which resulted in a filmed version intended for theatrical release.

Waitress, perhaps even more than Chicago, has been friendly territory for recording artists. American Idol alum Katharine McPhee and Jordin Sparks both played the lead, and Jason Mraz performed as the male lead as well.