Before she was a tabloid cover queen and star of her own reality show, Kourtney Kardashian (pictured) joined Brittny Gastineau, George Foreman III, Courtenay Semel, and a slew of other privileged celeb kids as they worked -- or mostly complained about working -- on a Colorado cattle ranch. (Jay Clendenin / Los Angeles Times)
An early entry in the “reality rich” category, this MTV 2003 reality show focused on Tommy Hilfiger’s daughter Ally (pictured) and her best friend, Jaime Gleicher, whose father was the founder of a multimillion-dollar luggage company. The rich besties were filmed trolling Manhattan with their Louis Vuitton bags and oversized glasses as they gossiped and went on shopping sprees. (Henry S. Dziekan III / Getty Images)
