This study compared the word-finding abilities of 26 young adults (ages 18–22 years), 26 young-old adults (ages 58–74 years), and 26 old-old adults (ages 75–93 years) on a confrontational naming test (Boston Naming Test) and a more spontaneous discourse test. The groups were matched in terms of gender (7 male, 19 female) and estimated IQ (M = 114). When participants were asked to narrate what they perceived in pictures (discourse test), the older adult groups committed significantly more word-retrieval errors than the younger adults. In contrast, results from the picture-naming test surprisingly revealed higher naming accuracy by the older adult groups. Subsequent examination of the picture-naming items revealed that four items appeared to be influenced by generational familiarity with the item. These results suggest that selection of cohort-free items for picture-naming tests is important when comparing across age-groups, and that tests of discourse may be better measures for assessing everyday word-finding difficulties in healthy older adults.