He is best known for his leading roles in the Broadway musicals Wicked – for which he has played Fiyero on-and-off from 2007 to 2019 – Next to Normal, and Pippin.
He subsequently played Thalia in Broadway's Xanadu from April 2008 until its closing that September, and Matthew in Altar Boyz Off-Broadway from October 2006 to June 2007.
Massey stayed with the show until it closed in January 2011, when he then returned to Broadway's Wicked, this time in the lead role of Fiyero.
[5] Following the closure of Lucky Guy, he returned to Wicked as Fiyero, covering for Richard H. Blake, who took a three-week absence to be with his newborn child.
[13] Massey grew up in Jonesboro, Arkansas where his father is a Certified Public Accountant and his mother is a teacher.