Pleural disease is common with an increasing incidence and so represents a significant proportion of the workload for respiratory physicians. Chest drain insertion continues to be considered a mainstay of pleural disease management however the optimum drain size required for various pleural conditions remains unclear. Traditionally large-bore chest drains were inserted through a surgical technique of blunt dissection however smaller bore Seldinger (guidewire) drains have dramatically increased in popularity in recent times most likely due to ease of insertion and perceived increased patient tolerability. Despite British Thoracic Society Guidelines advocating a preference for small-bore chest drains, their use remains controversial. We aim to review the literature in each category of pleural disease including pneumothorax, malignant pleural effusion and pleural infection, regarding chest drain size, comparing the role, effectiveness and complications of each.