From Sept 28 2010 until the show closed on Jan 9 2010, Stephen starred in the lead role of Fredrik in A Little Night Music opposite Bernadette Peters as Desiree. Stephen was a member of the original production, starring Catherine Zeta Jones and Angela Lansbury, which began previews at Broadway's Walter Kerr Theatre (219 West 48th Street) on November 24, 2009 with an official opening on December 13, 2009. He opened in the Quintet ensemble as Mr. Lindquist and was the understudy for Fredrik and Frid. On Aug 31, 2010 until he assumed the role of Fredrik, he played the role of Frid full time.

The original cast CD for A Little Night Music was released on April 6, 2010 on Nonesuch records.