After studying at the Atlantic Theater Company and recurring in iconic series such as Lost and Gilmore Girls: A Day in the Life, Tom can now be seen as the lead in feature film Love, Courage and the Battle of Bushy Run, portraying real life character Col. Henry Bouquet. Film critic Lee Brown raves "Connolly expertly displays Bouquet's steadfast courage and resilience", while critic Shane A. Bassett declares that "Connolly is the perfect casting accomplishment as Bouquet" describing Tom's performance as "brilliant". Tom recently won Best Actor at both the Her Vision International Film Festival and the LASFF for his lead role in the feature film Sallywood. He can soon be seen reprising his recurring role of Leander in Season 5 of the smash hit series The Chosen.