29, 2014, he was nominated for a Tony in the category of Best Actor in a Featured Role in a Musical. He appeared in the role of Noble Sissle in the 2016 production of Shuffle Along, or, the Making of the Musical Sensation of 1921 and All That Followed at the Music Box Theatre on Broadway. Henry starred as Jamie alongside Cynthia Erivo in a one-night benefit concert performance of Jason Robert Brown's The Last Five Years on September 12, 2016. Proceeds from the performance went to the Brady Center, a national gun violence organization. Henry had also performed in a one-night concert performance of another one of Brown's shows, Parade, at the Lincoln Center. In 2016 and 2017, Henry starred in the lead role of Aaron Burr in the first US tour and Chicago productions of Hamilton: An American Musical. In 2018, Henry starred as Billy Bigelow alongside Jessie Mueller in the third revival of Rodgers and Hammerstein's Carousel, for which he received a Tony Award nomination. On November 18, 2020, it was announced Henry would reprise his role of Burr in a special performance with the cast of Hamilton for the Macy's Thanksgiving Day Parade. In 2021, he starred as Dr. Pomatter in Waitress alongside Ciara Renèe. In May 2022, it was announced Henry would star as Rapunzel’s Prince in the Broadway revival of Into the Woods that would open in June of that year. He left the production on October 9 for the filming of Beauty and the Beast: A 30th Celebration and was replaced by Andy Karl. Henry returned to the production after Karl’s extended run ended December 2. Henry would stay with the production until its final performance on January 8, 2023. During the run he would star opposite Gavin Creel, Cheyenne Jackson, Karl, Sara Bareilles, Brian d'Arcy James, Patina Miller, Stephanie J. Block, Montego Glover, Joaquina Kalukango, Sebastian Arcelus, Phillipa Soo, and Krysta Rodriguez. Film and television Henry appeared in the first Sex and the City film in 2008. Henry has also appeared on the television series Kings and Nip/Tuck, as well as the 2010 short film Once Upon a Time in Australia. Henry also appeared in the role of Corporal Quincy Montclair on season 7 of the Lifetime series Army Wives. Henry also starred in the film adaptation of Jonathan Larson's musical tick, tick... BOOM! as Roger Bart. He starred alongside Andrew Garfield,