The humor appeal is extensively used in advertising, but its impact is not clearly understood in the context of luxury brand advertising. This research therefore examines the role humor appeal in luxury advertising plays in customers’ evaluation of the brand, advertisement, and purchase behaviors toward the firm. Specifically, this study proposes that the use of a humor appeal in luxury advertising has a favorable influence on perceived luxuriousness of the brand, attitude toward the advertisement, and purchase intention through coolness perception of the luxury brand. Furthermore, this study explores the moderating roles of brand positioning appeal (top-dog vs. underdog) and desire for distinction. This study is one of the few to examine the influence of humor appeal in luxury brand advertising, providing evidence for the applicability of humor appeal in luxury advertising. The study findings will help luxury brand managers make informed decisions about when and how to use humor in advertising to achieve desirable advertising outcomes.