[20] The musical premiered on Broadway, starting in previews on February 14, 2008, with an official opening on March 9, 2008, at the Richard Rodgers Theatre.
[23][31] Kail reunited with Lombardi playwright Eric Simonson on Magic/Bird, a new play chronicling the intertwined life stories of basketball Hall of Famers Larry Bird and Earvin "Magic" Johnson.
Kail directed, with the cast that featured Kevin Daniels as "Magic" Johnson and Tug Coker as Larry Bird.
[32] Kail continued his collaboration with Lin-Manuel Miranda, directing the musical Hamilton in 2015, both Off-Broadway and on Broadway, for which he won a Tony Award.
[33] Kail directed Grease: Live for Paramount Television, screened live on Fox on January 31, 2016;[34] the world premiere of Dry Powder with Hank Azaria, Claire Danes, John Krasinski and Sanjit De Silva which ran from March to May 2016 at The Public Theater in New York City;[35] and Tiny Beautiful Things, also at The Public, from November to December 2016.
Kail was nominated for Outstanding Directing – Movies for Television and Limited Series by the Directors Guild of America for the episode "Nowadays."
In May 2023, it was announced that Kail would direct a live action adaptation of the Disney animated film Moana, making his narrative feature directorial debut.