Bennett Cullen began his dance training in the suburbs of Chicago before continuing his classical education at the University of Iowa, where he studied ballet under Eloy Barragan, George De La Peña, and Kristin Marrs. Since graduating, Bennett has performed professionally with St. Louis Dance Theatre, Visceral Dance Chicago, Trifecta Dance Collective, Bodies of Water Dance, Cerqua Rivera Dance Theatre, Ballet Harmony and EnbyBallet.

Bennett has had the privilege of performing works by internationally acclaimed choreographers including Ohad Naharin, Jiří Kylián, Nacho Duato, Christian Spuck, and Marguerite Donlon, as well as Brian Enos, Shannon Alvis, Stephanie Martinez, Michelle Manzanales, Katlin Bourgeois, Monique Haley, Nick Pupillo, Sarah Olsen, Marc Macaranas and Omar Roman De Jesus.

In addition to performing, Bennett is a dedicated educator and coach, teaching ballet technique and mentoring dancers at numerous institutions throughout the Chicagoland area. His passion for cultivating artists extends beyond the studio through arts leadership and administration.

From 2022–2024, Bennett served as Executive Assistant and Educational Coordinator for Cerqua Rivera Dance Theatre. He currently serves as Director of CRDT II, the organization's second company, and as Rehearsal Director for Cerqua Rivera Dance Theatre. Bennett also works as an administrator for Bodies of Water Dance, supporting organizational development while continuing an active career as a performer, educator, and arts leader.