RW/RR Challenge: Challenge 99'

The Real World/Road Rules Challenge is the first six-on-six Challenge in the series and is sometimes incorrectly remembered as the first season although one season officially preceded it. The teams traveled via tour bus and RV starting in San Francisco, California, ending in Universal City, California competing in different individual challenges. The winning team had the right to travel in a tour bus, while the losing team had to travel in an RV. Each time a team won an individual challenge, they won the right to spend time in a "money machine". The "money machine", set up outside Universal Studios Hollywood in Universal City, California was a huge wind chamber that contained up to $150,000. Whatever the casts could keep on them, they were guaranteed to keep. This season also featured an additional challenge where the two teams competed over possession of a teddy bear. Whichever team had the teddy bear in their possession at an unknown, predetermined point in the challenge, would win the additional challenge.