Cobby started singing while attending Ealing Academy, before becoming a chorister at Worcester College, Oxford and, later, the City of Oxford High School for Boys, where he won a competition to perform at St Paul's Cathedral.
From his early days at Ealing Academy, Cobby developed a passion for singing. He went on to become a chorister at Worcester College, Oxford and then the City of Oxford High School for Boys, where he achieved recognition by winning a competition to perform at St Paul's Cathedral.