"Sex and the City" (1998, 1999)


Trump made multiple cameos on the series, including the season two episode "The Man, the Myth, the Viagra" in which Trump's friend (played by Bill McHugh), who is over 70 years old, attempts to seduce Samantha (Kim Cattrall).

http://www.hollywoodreporter.com/lists/donald-trump-18-memorable-cameos-873520/item/sex-city-donald-trump-cameos-873565