Massey first joined the North American touring production of
Wicked in 2007, as part of the ensemble and
understudy for the lead role of
Fiyero, before joining the
Broadway production. 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. From June to September 2009, he temporarily played the role of Gabe in the Broadway musical
Next to Normal, after which he remained as a cover for the role, before assuming the role permanently in January 2010. 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. He left in March of that year to star in
Lucky Guy, which opened Off-Broadway in April 2011. 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. He later returned to the touring production of
Wicked, playing
Fiyero from November 2011 through February 2012. On July 31, 2012, he once again joined Broadway's
Wicked as Fiyero until May 26, 2013. He played the role again in the Broadway production from December 2013 to February 2014. He appeared in 2012
Broadway Bares with
Miriam Shor. In August 2013, he played Tony in
The Muny production of
West Side Story. On April 1, Massey assumed the title role in the Broadway revival of
Pippin. He finished his run on October 29. On January 23, 2015, it was reported that Massey was cast in a recurring role as openly gay country music songwriter Kevin Bicks in the ABC television musical drama series
Nashville. ==Personal life==