Each Challenge pits numerous cast members from past seasons of reality shows against each other, dividing them into two separate teams according to different criteria, such as gender, which show they first appeared on, whether or not they're veterans or rookies on the show, etc. The two teams compete in numerous missions in order to win prizes and advance in the overall game.
Air date: 1998-11-09
Runtime: 20 min
Overview: We start off with six ex-Real Worlders and six ex-Road Rulers being led into a baseball stadium blindfolded. We then see a limo being followed by a armored truck. Inside the limo is this year's Mr. Big - David from the Real World Los Angeles. We are introduced to our teams- Real World Beth from Real World Los Angeles Neil from Real World London Jason from Real World Boston Montana from Real World Boston Janet from Real World Seattle Nathan from Real World Seattle Road Rules Mark from Road Rules 1 Kayle from Road Rules Islands Kefla from Road Rules Australia Anne from Road Rules Northern Trail Roni from Road Rules Northern Trail Noah from Road Rules Northern Trail From his limo, David is patched over the PA system in the stadium. He tells the players that they can take off their blindfolds and they have to look for the gold dollar. A helecopter flys over with a bag and drops thousands of fake money with David's picture on it.
Air date: 1998-11-16
Runtime: 20 min
Overview: They arrive in Mammouth Lakes CA, where their next mission will take place. In their campsite, they find a newspaper that has a article about their mission. It says that casts of the Real World and Road Rules will take part in the yearly Frontier Day's Bed Race. There is talks about whether Beth should stay in the challenge or not. Beth wants the cash so she is gonna stay, but Neil says she better work if she wants a piece of the cash. The Real World team is starting to get close to their rundown RV which they have now named ""Bessie"". So, they take it to a gas station and they buy lots of spray paint and both teams leave their marks on the RV. They arrive at the mission site, they are told they will be taking part in a Bed Race. Each team must dcorate a bed as wild as possible and then it will be placed on wheels and they will have to race it down a hill. The team with the best of out 3 races will win a minute in the Money Chamber and the luxory bus.
Air date: 1998-11-23
Runtime: 20 min
Overview: They are heading to the Hollywood YMCA where both teams know they have to work, but not sure on what they'll be doing. The Real World team is tired of losing and Neil is wondering why he even decided to do this challenge. They arrive at the YMCA, and the ladies and men are seperated in different locker rooms. They are given basketball jerseys to change into. The teams walk out on a basketball court where Kobe Bryant and Reggie Miller are playing. The only ones that recognize them are Kefla, Roni, and Nathan. Since Road Rules has ""Japenese Pacers"" they get to play against Kobe and Reggie in a basketball match. Their special referree is Syrus from Real World Boston. For each time Road Rules scores a basket, they receive $20. But for each time Kobe or Reggie score a basket, $10 of Road Rules money goes to them. Real World has ""Snoop Doggy Doggs"" where they have to bathe Kobe Bryant's dogs.
Air date: 1998-11-30
Runtime: 20 min
Overview: We start back with Janet still freaking out at the top. Her hands have formed into fists and they won't open. The Bungee Master tells her that she is having some sort fo spasms. She still wants to jump but he tells her to go back down, rest alittle, and she can come back up. Back on the boat, Kefla and Roni start freaking out that it isn't fair that Janet got to come back down. The Bungee Master finally stops all the fighting by telling them that it wasn't her choice to come back down, it was his. Kayle goes up and gets no rings. Nathan tells Beth and Montana that if Anne gets any rings they're gonna have to jump and they refuse. Anne jumps and gets one ring giving Road Rules a one ring lead. Janet finally recovers and jumps, she doesn't get a ring, but that doesn't matter to the team who is happy that she faced her fear. The pressure has come down to Beth and Montana, Montana doesn't want to jump cause it's her worst fear and Beth doesn't want to do a one legged jump.
Air date: 1998-12-07
Runtime: 20 min
Overview: After the Talent Show, Real World is on Cloud 9 cause they finally have won a mission. Backstage they receive their next clue - ""Left, Left, Left, Right, Left. I don't know if it's been said, this mission can make you dead. Sound off, Real World, Sound off, Road Rules, Sound Off, Let's Fight!"" Nathan is excited cause he knows it has something to do with the Military which he is actively involved in. The girls seem to be upset cause they know it'll involve physical strength. They are told they need to be at Camp Pendelton in Southern California by 6pm the following day. Since it's their final night in Vegas, they decide to hit the town again. Flirtation continues between Montana and Noah. The following morning, Roni looks for Noah, but can't seem to find him. Nathan tells her to look in the girls room and see if Montanas there.
Air date: 1998-12-14
Runtime: 20 min
Overview: We start right back in at the Playboy Mansion. The Playboy Bunny tells them to leave their stuff on the front lawn cause she's gonna take them on a tour of the property. They see exotic birds, monkeys, and other animals. She takes them by the famous pool and grotto, she also tells them that they will be spending the night in the game room where there are seperate beds bracnhed out of the main room. They arrive in the room to find there are special Hef P.J.s each with their name on it for each of the castmates. The Playboy Bunny invites them all out to the pool where all the guys socialize with the Bunnies while the girls sit back and talk trash. The man himself - Hugh Hefner comes out and welcomes them all to the Mansion. Noah finds a playmate that he could talk to and Montana gets jealous, she finds them alone and insults the both of them which extremely pisses off the playmate. She takes off to try and find Montana and confront her, but Noah holds her back.
