Morrissey made his first appearance in a Tony Marchant drama playing Michael Ride in "Into the Fire" (1996), and the following year played the lead role of Shaun Southerns in Marchant's BBC series "Holding On" (1997). Southerns, a crooked tax inspector, was the first of many "men in turmoil" roles for Morrissey, and it earned him a nomination for the Royal Television Society (RTS) Programme Award for Best Male Actor the next year. In 1998, he appeared in "Our Mutual Friend" alongside Paul McGann. As he was a fan of the book, Morrissey asked director Julian Farino if he could play Eugene Wrayburn, but the role went to McGann. Farino had Morrissey in mind to play schoolmaster Bradley Headstone, a part Morrissey was reluctant to take until he read the script. He studied the role and decided to take it on the basis that the character was unloved and that his motivation by social class causes his mental health problems. His performance was described by a writer for "The Guardian" as bringing "unprecedented depth to a character [...] who is more commonly portrayed as just another horrible Dickens git." In the same year, he played Christopher "Kiffer" Finzi in Anand Tucker's "Hilary and Jackie". His roles in "Our Mutual Friend" and "Hilary and Jackie" were described as his breakthrough roles by Zoe Williams of "The Guardian".