This paper examines variation and change in the adjectives used to express “highly positive evaluation” in the varieties of English spoken in Toronto, Canada, and York, England. Building on earlier work on another semantic field, “strangeness,” we analyze over 4800 tokens and thirty-four different types, as in “That’s great” and “She’s awesome.” Our results show both similarities and differences between these two semantic fields. While individual forms in both fields tend to be popular for a long time, many forms fall in and out of favor. In the case of adjectives of highly positive evaluation, the adjectival set is particularly rich. Distributional analysis and statistical modeling of constraints on the major forms and their underlying social and linguistic correlates reveals that these changes are not progressing in parallel across varieties of English. There are robust linguistic patterns that suggest a systemic underlying explanation. New additions to this field arise in predicative position and as stand-alones, and in a later stage extend to attributive position. Finally, consistent with earlier findings on adjectives and (intensifying) adverbs, there are notable links to social trends and popular culture, affirming the link between open class categories and their sociolinguistic embedding.