The Humor Styles Questionnaire (HSQ) is one of the most popular self-report scales in humor research. The present research conducted a forward-looking psychometric analysis grounded in Rasch and item response theory models, which have not been applied to the HSQ thus far. Regarding strengths, the analyses found very good evidence for reliability and dimensionality and essentially zero gender-based differential item functioning, indicating no gender bias in the items. Regarding opportunities for future development, the analyses suggested that (1) the seven-point rating scale performs poorly relative to a five-point scale; (2) the affiliative subscale is far too easy to endorse and much easier than the other subscales; (3) the four subscales show problematic variation in their readability and proportion of reverse-scored items; and (4) a handful of items with poor discrimination and high local dependence are easy targets for scale revision. Taken together, the findings suggest that the HSQ, as it nears the two-decade mark, has many strengths but would benefit from light remodeling.