After moving to Chicago in 2011, Gabriel Di Gennaro had the pleasure of working with many of the vibrant companies in and around its neighborhoods including VOX 3 Collective, Main Street Opera, The Gilbert & Sullivan Opera Company, /kor/ productions, Opera Ouvert, Third Eye Theatre Ensemble, Music Theater Works, Evanston Chamber Opera Company, Floating Opera Company, Chicago Fringe Opera, Folks Operetta, Petite Opera Productions, and Thompson Street Opera.
An avid supporter of new music, Gabriel performed several regional, American, and world premieres on both the operatic and concert stages. Close collaboration with New York City-based composer Scott Wasserman birthed two world premieres in a setting of Shel Silverstein’s The Giving Tree and the cycle Even for Wars, a duet of letters written between soldiers and their loved ones. Additional unique performance experiences were Golaud in a lecture recital of Pelléas et Mélisande presented by Richard Stilwell, and The Dance Master/Mars in Carl Nielsen's Maskarade, the first of many times Gabriel would be featured as both a singer and a dancer in an opera.
In 2012, the Young Singers Foundation selected Gabriel as one of 17 national recipients of their Bev Sellers Memorial Scholarship, helping to further his education at the Chicago College of Performing Arts at Roosevelt University. In addition to Roosevelt, Gabriel is an alumnus of the University of Delaware, OperaWorks, and the College Light Opera Company with participation in the young artist programs of Cedar Rapids Opera Theatre, Pittsburgh Festival Opera, and Chicago Summer Opera.