A toolbar displays dynamically configured controls based on a size of a window in which an application is running and on the media type presented. A large set of available controls may be available for the toolbar; however, the size of the application window in which the application is running may not be able to display all of the available controls in the window in such as way as to be comfortably used by a user. Accordingly, the controls may be scaled, filtered, and interchanged according to the “real estate” available in the application window, as well as other contextual aspects of the application, to provide a more user-friendly experience.