Henry was born in Winnipeg, Manitoba, Canada to Zadoc Henry (a teacher at Calvary Christian Academy), and raised in Miami, Florida, United States. He currently resides in Harlem, New York City. He had originally wanted to be an accountant, like his mother. However, he was cast as Harold Hill in his high school (Florida Bible Christian School) production of The Music Man and with the experience he changed his mind. Henry studied theatre at the University of Miami, graduating in 2006. He married his college sweetheart, Cathryn Stringer, in October 2012.
Henry made his acting debut when he co-starred as Judas in the Paper Mill Playhouse (Milburn, New Jersey) production of Godspell in 2006. He was set to star in a 2008 Broadway transfer, but the project was cancelled.
In 2007, Henry appeared in the ensemble of the Off-Broadway musical In the Heights, re-joining the cast for the show's Broadway production. For In the Heights, the entire cast won a Drama Desk Award, and Henry and the ensemble won an ACCA Award for Outstanding Broadway Chorus from Actors' Equity Association.

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