Massey made Daytime Emmys history with his three consecutive wins in the Younger Actor category. Whilst he is the second actor to win the category three times – following Jonathan Jackson, who won for General Hospital in 1995, 1998, and 1999 – he is the first to do so in consecutive years. Massey is also the first actor from Days of Our Lives ever to win three Emmys, consecutive or otherwise.
Massey is currently nominated for the 2018 Daytime Emmy Award for Outstanding Supporting Actor in a Drama Series. The results are expected to be announced in the Daytime Emmy Award ceremony at Pasadena on April 29, 2018.
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.
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 made Daytime Emmys history with his three consecutive wins in the Younger Actor category. Whilst he is the second actor to win the category three times – following Jonathan Jackson, who won for General Hospital in 1995, 1998, and 1999 – he is the first to do so in consecutive years. Massey is also the first actor from Days of Our Lives ever to win three Emmys, consecutive or otherwise.
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 would reprise the role of Will, and his new episodes began airing on September 15, 2017.
Massey is currently nominated for the 2018 Daytime Emmy Award for Outstanding Supporting Actor in a Drama Series. The results are expected to be announced in the Daytime Emmy Award ceremony at Pasadena on April 29, 2018.
