Real World/Road Rules Challenge is the 2nd season of the MTV reality game show, The Challenge (sometimes incorrectly referred to as the show's 1st season). The season is directly subsequent to Road Rules: All Stars.

The season marked the first time in which "Real World/Road Rules Challenge" would be used as the show's main title (by the 19th season, however, the program would be renamed yet again simply to the The Challenge). In addition, it's one of two seasons absent of a subtitle (though the other, season 3, did have the year of its production as part of its title), a trend that wouldn't truly emerge until the show's 4th season.

It is the first six-on-six Challenge in the series. The teams traveled via tour bus and RV starting in San Francisco, 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.


Host: David Edwards, aka Mr. Big, from The Real World: Los Angeles

Real World team
Player Original season
Beth Stolarczyk Los Angeles
Janet Choi Seattle
Jason Cornwell Boston
Montana McGlynn Boston
Nathan Blackburn Seattle
Neil Forrester London
Road Rules team
Player Original season
Anne Wharton Northern Trail
Kalle Dedolph Islands
Kefla Hare Down Under
Mark Long USA - The First Adventure
Noah Rickun Northern Trail
Roni Martin Northern Trail

Episode GuideEdit

Episode 1 – "Money Changes Everything"

  • First aired November 9, 1999
  • Six cast members from The Real World and Road Rules each are brought in to compete in 6-on-6 challenges for money; Beth sustainsan injury;JanetandJasonbegina flirtatious relationship.
  • Mission: Roller Derby Mission Winners: Road Rules

Episode 2 – "Bed Sores"

  • First aired November 16, 1999
  • Beth's ankle injury handicaps the Real World team; Janet and Jason continue to get closer; the Road Rules team annihilates the Real World team in the next challenge.
  • Mission: Roller Derby Mission Winners: Road Rules

Episode 3 – "Getting Drunk"

  • First aired November 23, 1999
  • Janet's fear of heights threaten the Real World team another challenge; Roni and Kefla spark their relationship more when they hit the club alone.
  • Mission: Ring Around the Bungee Mission Winners: Road Rules

Episode 4 – "The Joint is Jumping"

  • First aired November 30, 1999
  • Janet takes the leap; The Real World team is desperate for a win; Beth gets aggravated when the team pardons Montana, but excoriated Beth for not completing the mission; Montana and Noah begin a cross-team fliratious relationship.
  • Mission: Playing Vegas Mission Winners: Real World

Episode 5 – "Shall We Play A Game?"

  • First aired December 7, 1999
  • Montana and Noah's flirtation causes controversy; the teams face a difficult military-based challenge.
  • Mission: War Games Mission Winners: Road Rules

Episode 6 – "Handsome Reward"

  • First aired December 14, 1999
  • The final challenge for the money chamber looms; Montana gets jealous when she catches Noah talking to a playmate at the Playboymansion; Anne hurts herselfina trampoline accident; Janet and Jason's relationship heats up, causing production to step in.
  • Mission: Handsome Reward Mission Winners: Road Rules Bank account Real World - $10,240 $1706 each Road Rules - $39,680 $6613 each Additional challenge: Teddy Bear Steal Mission Winners: Real World

Final ResultEdit

Team Road Rules wins the "money chamber" challenge walking away with the most money. Team Real World wins the teddy bear challenge, which ended in Las Vegas, Nevada at the Hard Rock Hotel and Casino.