Massey was awarded the Daytime Emmy Award for Outstanding Younger Actor in a Drama Series three years in a row – in 2012, 2013, and 2014, and is the first actor ever to receive a Daytime Emmy Award for playing a gay character. In 2018, Massey was nominated for the Daytime Emmy Award for Outstanding Supporting Actor.
Massey was born and raised in Atlanta, Georgia. He is the son of Lewis A. Massey, former Secretary of State of Georgia, and Amy Reichard Massey. He has two younger siblings: Cameryn and Christian.
He graduated from Norcross High School in May 2009. While there, he was active in its drama club and took part in many of the school productions, including playing the lead roles in Little Shop of Horrors, One Flew Over the Cuckoo's Nest, Guys and Dolls and How to Succeed in Business Without Really Trying.
Later that year, he moved to Los Angeles to attend the University of California at Los Angeles (UCLA) and to pursue an acting career. At UCLA, he played on the Ultimate Frisbee team, where he was given the nickname "Bamm Bamm." While working on Days of Our Lives, Massey roomed with his friend and Days co-star Casey Deidrick.
Days of Our Lives In December 2009, after completing his first quarter at UCLA, Massey successfully auditioned for the role of Will Horton on NBC’s daytime drama Days of Our Lives, joining the cast in 2010. He had previously auditioned for Will when Dylan Patton was cast. For this role, Massey became the first actor in history to win a Daytime Emmy for portraying a gay character, when he won the Outstanding Younger Actor category in 2012. He had been nominated in the same category the previous year. In February 2013, Massey's younger brother, Christian, appeared as a young Will Horton on Days of Our Lives in a flashback.
In June 2013, Massey won his second consecutive Daytime Emmy for Outstanding Younger Actor. Massey revealed that he intended to return to school instead of renewing his contract, which was set to expire in December 2013.[ Days executive producer Ken Corday stated that his character would not be recast, and that the door would be open in case Massey decided to return; but Massey expressed that he would support a recast. On August 23, 2013, it was announced that Massey had taped his final episode that day, and that a recast had already been made. Massey was let out of his contract early, for which he thanked Days and NBC. On June 22, 2014, Massey won his third consecutive Emmy for Outstanding Younger Actor in a Drama Series.
On May 8, 2017, Entertainment Weekly announced that Massey was reprising the role of Will on Days of Our Lives, and Massey expressed excitement at bringing the character back. His new episodes began airing on September 15, 2017. Kristyn Burtt of SheKnows said Massey's return was a "huge watershed moment" for the network; in 2018, Massey was again nominated for a Daytime Emmy Award, this time for Outstanding Supporting Actor.
Massey has made guest appearances in several drama series, including One Tree Hill and Army Wives, as well as appeared in the HBO comedy series, Eastbound & Down. In 2010, he starred in his first feature film, 16-Love, in which he portrayed Farrell Gambles, a fun-loving junior tennis player, and the love interest of Lindsey Shaw's lead character, Ally Mash. Backstage wrote that he gave "levels to his character" as the "boyish, smitten, too-romantic-to-be-true athlete next door." Following its release in January 2012, the film topped iTunes' Sports Movies chart for several weeks.
Massey is also a musician, serving as the keyboardist and one of the two clean vocalists in the metal band And Still I Rise.