In December 1998 the National Gallery of Art, Washington DC, working with Cognitive Applications of Brighton, England, published The National Gallery of Art Washington CD-ROM. This publication is the latest generation in the family line that began at the National Gallery in London when the original Micro Gallery, conceived way back in 1987, was delivered in July 1991. Each generation of this family inherited a good deal from its forebears, and as we might hope and expect, through fresh inputs and evolution, advanced beyond them. This paper examines the interaction between advances in multimedia technologies, experience and audience expectations, and the evolving requirements of museums and cultural institutions, through the common characteristics and evolving trends in a "family" of applications. Each application was designed for longevity and on time and on budget delivery, which meant that specific technology boundaries of its time needed to be respected. Other family characteristics that have emerged include inheritance of valuable assets from generation to generation, increasing affordability and ease of development, and that joint venture, self-published, commercial products have become a financial reality. This paper looks at the concrete changes introduced in past projects but focuses on future directions indicated by market and technological potential.