David Smith presents an overview of some of the challenges and difficulties faced by the regulation in applying Data Protection standards and rules to freedom of expression. David Smith, Deputy Commissioner and Director of Data Protection at the UK Information Commissioner's Office, focuses on exploring the challenges in deciding when and how the law applies, the definition of journalism literature and art, the complexity of UK law in this area and the political nature of regulation the media. The talk was the keynote address of the OxPILS Conference 'The 'Right to be Forgotten' and Beyond' held on 12 June 2012. This Conference was the culmination of 'Mending the Tangled Web? Information Privacy 3.0', a series which was generously made possible with funding from a Joint Programme between the European Union and the Council of Europe. (The views expressed are those of the individual speakers only). For full details please see http://www.csls.ox.ac.uk/conferences/oxpilsconference2012/.