Connelly is the first man ever to have become a Barbershop Harmony Society International Championship gold medalist four times, first with Interstate Rivals in 1987 at the age of 22, then with Keepsake in 1992, with Platinum in 2000, and with Old School in 2011.
Quartet-mate Tony DeRosa joined Connelly as a four-time gold medalist in 2017 (in Keepsake, Platinum, Max Q and Main Street).
A few other singers have achieved the honor of being three-time champions, including quartet-mate Kipp Buckner (in The Gas House Gang, Interstate Rivals, and Old School).
[2][3] He coaches men's and women's barbershop quartets and choruses around the world full-time, having become one of the few barbershoppers who has turned his hobby into a profession.
[4] He currently performs around the world with his quartet, Old School, which took the silver medal in international competition in 2009 and 2010, before winning the gold in 2011.