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.

Road Rules: All Stars

Road Rules: All Stars is the first season and original title of the MTV reality television game show, Real World/Road Rules Challenge. The first season of the show premiered on June 1st, 1998. Five alumni from past seasons of The Real World were brought together to participate in a series of missions as they travelled across the United States and New Zealand in a Winnebago. Unlike following seasons of Real World/Road Rules Challenge, this season only consisted of cast members from The Real World and was made up of a much smaller cast. As with Road Rules, all of the cast's cash and credit cards were confiscated for the duration of the series, and if the participants completed all the assignments, they would win a "handsome reward". At the end of the series, each cast member won a trip for two to Puerto Rico.

Cast:
Eric Nies (RW1: New York)
Jon Brennan (RW2: Los Angeles)
Rachel Campos (RW3: San Francisco)
Cynthia Roberts (RW5: Miami)
Sean Duffy (RW6: Boston)
David "Puck" Rainey (RW3: San Francisco)[Roadmaster]

Memorable Moments:

• The Road Rules: Northern Trail cast handed off the keys to the Winnebago after their season ended in Lake Placid, New York.
  
• One assignment required the cast to perform on stage in front of an audience, with each cast member reenacting memorable moments from their respective season of The Real World. Eric reenacted the Afrocentric viewpoints of his housemate, Kevin Powell, which Powell had expressed when the two had an argument on the issue of race. Jon put on a black spiked wig and spoke in a thick Irish accent in imitation of his housemate, Dominic Griffin. Rachel imitated housemate David "Puck" Rainey, with whom she and her other housemates had a very contentious relationship. Cynthia simulated the act of lifting her shirt to expose her breasts, as housemate Flora Alekseyeun had done more than once during the Miami season.
  
• Rachel refused to put on the Hot Dog on a Stick uniform in Venice Beach, California because it would upset her parents and demean her education.
  
• Cynthia criticized Rachel for behavior that she felt stemmed from an attraction between her and Eric.
  
• As a practical joke, the male contestants were assigned to cook a meal for the women, which included a soup filled with dead insects, unbeknownst to Rachel and Cynthia. After consuming the soup, the women were told the soup's ingredients, which upset Cynthia so much that she threatened to leave the show.
  
• The team received an assignment from a mysterious character named Mr. Big. When they finally met him, it was revealed to be David "Puck" Rainey.
  
• Rachel and Sean fell in love, would eventually marry, and have several children.