Iglehart assumed the roles of the Marquis de Lafayette and Thomas Jefferson in the Broadway cast of Hamilton in April 2017.

More recently, Iglehart joined the casts of animated webseries Helluva Boss (as both the Demon Lord of Lust Asmodeus/Ozzie and hellhound bodyguard Vortex) and Hazbin Hotel (as Zestial), as well having written for Marvel Comics, primarily one-shots featuring Spider-Man.

He started his career in California, performing in Bat Boy at TheatreWorks in Palo Alto and as Teen Angel in Grease at the American Musical Theatre in San Jose.

[11] Iglehart guest starred in four episodes of Unbreakable Kimmy Schmidt as Coriolanus Burt, the rival of male protagonist Titus Andromedon.

Iglehart voices Vortex and Asmodeus in Helluva Boss, Lance Strongbow in Tangled: The Series, Captain James Hook in Cheshire Crossing by Andy Weir, Bronzino in Elena of Avalor, Oscar in Vampirina and Taurus Bulba in DuckTales.

[16] In October 2023, Iglehart assumed the lead role of A Wonderful World, a new musical based on the life of Louis Armstrong in its pre-Broadway New Orleans and Chicago engagements.