The term “pimping” was popularized by Brancati1 in 1989. As he defined it, pimping occurs when an attending physician (the Pimper) poses a series of difficult questions to a resident or medical student (the Pimpee). Pimping usually occurs in settings such as “morning report” or “attending rounds,” in which trainees at various levels convene with a faculty member to review patients currently under their care. Among surgeons, pimping may occur when students and residents are a captive audience observing a patient undergoing an operation. Brancati1 described the origins of the term, which date back to 17th-century London. Koch's series of “Pümpfrage” (pimp questions) were used on his rounds in the 19th century. The practice migrated to North America in the 20th century and was documented by Flexner while observing Osler making rounds at Johns Hopkins. Brancati1 outlined suggestions for attending physicians to further hone their pimping skills and methods for students to defend themselves from it. He posited that the art of pimping would disappear in the future with increased specialization and educational reorganization. This Commentary revisits the art of pimping 20 years later and provides an update for faculty members and students alike on modern methods in this important skill.