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The Challenge (1998 – ...)

1998 • 42 seasons • Reality • TV-14
On September 20, 2026
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All seasons

The ChallengeReal World vs. Road Rules

6 episodes · Nov 9, 1998

Following directly after *Road Rules: All Stars*, Season 2 of *The Challenge* – then officially branded as *Real World/Road Rules Challenge* for the first time – kicked off a cross-country competition unlike any seen before. This season distinguished itself as one of only two in the early years to forgo a subtitle, setting the stage for future naming conventions. For the very first time, the show pitted six *Real World* veterans against six *Road Rules* stars in a head-to-head battle across America. The teams embarked on an epic journey by bus and RV, starting their adventure in San Francisco and culminating in Universal City, California, tackling individual challenges along the way. Victory came with a luxurious perk: riding in the comfortable tour bus. Defeat? Cramped quarters in the RV. Adding a unique twist to the competition was the "money machine," a massive wind chamber packed with up to $150,000 located just outside Universal Studios Hollywood. The winning team of each challenge got to test their luck against the gusts, keeping whatever cash they could hold onto. And in one particularly playful challenge, teams fought for control of a single teddy bear – whoever held it at a secret moment would claim victory.

1. Money Changes Everything
Nov 9, 1998 · 20m

Six former cast members from *Real World* and six from *Road Rules* are blindfolded and led into a baseball stadium. Simultaneously, a limousine is followed by an armored truck. Inside the limousine sits this season’s Mr. Big, David, from *

2. Bed Sores
Nov 16, 1998 · 20m

They arrive in Mammoth Lakes, California, the location of their next undertaking. At their campsite, a newspaper awaits, featuring an article detailing their mission. It mentions that casts from *The Real World* and *Road Rules* will be par

3. Getting Drunk
Nov 23, 1998 · 20m

The teams made their way to the Hollywood YMCA, both aware of the work ahead, though uncertain of its precise nature. The Real World crew, weary of defeat, found themselves questioning the wisdom of undertaking this challenge. Upon arrival,

4. The Joint is Jumping
Nov 30, 1998 · 20m

Janet remained frozen at the platform's peak, her fists clenched tight, refusing to release. The Bungee Master explained she was experiencing some kind of spasm, but her desire to jump persisted. He urged her to descend, rest, and try again

5. Shall We Play a Game?
Dec 7, 1998 · 20m

Following the Talent Show, Real World buzzed with exhilaration – they had finally secured a mission. Backstage, their next clue awaited: "Left, Left, Left, Right, Left. It’s been whispered, this mission could prove fatal. Sound off, Real Wo

6. Handsome Reward
Dec 14, 1998 · 20m

The scene returns to the Playboy Mansion. A Playboy Bunny instructs them to leave their belongings on the front lawn, as she will be giving them a tour of the grounds. They are shown a collection of exotic birds, monkeys, and other creature

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