Some of these paintings hung for many years in St. Mary's Hall, the old town hall. They were part of a group of portraits of monarchs and benefactors. The best pieces were mostly gifts, some accepted because of a misunderstanding (the d'Heere), and some because of political intrigue (the Lawrence). In the 1950s Lord Kenilworth bequeathed an important group of paintings to help found the Herbert. More recently, the Herbert has obtained paintings by purchase or bequest.

In this room the pictures cover the walls from floor to ceiling.