25. All-Stars (1998)
The first installment, misleadingly called Road Rules: All-Stars, featured Real World alums participating in their own season of Road Rules. Without the season, we wouldn’t have had the next 24 installments, but considering it was a non-competitive show without any Road Rules cast members, it barely counts.
24. Real World vs. Road Rules (1999)
Improving on the original, this season had Real Worlders and Road Rulers face off, but the format was still a Road Rules clone (RV travel, “missions” in different cities). And as the show was still in the pre-Survivor era, there weren’t any eliminations, which is such a key component of the show that it places 24th on the list.
23. The Island (2008)
The Island was a terrible format: no challenges, no elimination battles, and no food. When Abe asked to be eliminated because he could be making more money at his “real” job at home, you knew something was wrong. This season did lay some valuable groundwork for future drama (Ev “selling her soul to the devil” and sailing to victory with the boys, and Kenny and Johanna’s ocean hookup), but that was all this lame season gave us.
22. Challenge 2000 (2000)
More early installment weirdness: There was a strange E-Trade-sponsored stock market subplot on this season (and the one that followed) that should never have been marketed at an MTV audience, still no eliminations and… those bucket hats.
21. Extreme Challenge (2001)
Real World alums were often the underdogs (in the challenges where they were split into teams by show-of-origin), and Extreme Challenge was the first time that RW took home the victory with a stacked team. Also, Tina Fey was there as a guest judge on the “No Laughing Matter” mission for some reason.
20. Battle Of The Sexes 2 (2004)
The second installment of Battle Of The Sexes, filmed after both The Gauntlet and The Inferno introduced the all-important elimination round, suffered from returning to the basic “both teams eliminate a player simply by voting” strategy. Also, after the blowout that was the first Battle Of The Sexes, the Bunim-Murray team should have known the boys would destroy the ladies and make for kind of depressing TV. This season is also notable for the weakest non-gameplay elimination in the show’s history when Steven playfully slapped Shane and was immediately ejected.
19. The Gauntlet (2003)
Eliminating players helped the game, but this season was a far cry from the down-and-dirty battles of Under Armour-clad folks we get these days. We owe all modern Challenges to The Gauntlet, but that doesn’t make it great.
18. The Inferno (2004)
The Inferno improved slightly on its predecessor by adding the life shield, which allowed the person nominated for elimination to save themselves. In addition to adding drama, the life shield added additional challenges, which made it a better show.
17. Battle Of The Sexes (2003)
The boys may have been the inevitable winners, but in the first installment of Battle Of The Sexes there was still tension and novelty when it came to the missions. Battle Of The Sexes was also the first Challenge hosted by Olympic gold medalist Johnny Moseley, who ranks behind all-star TJ Lavin, but lightyears ahead of Dave Mirra in the Challenge-hosts list. (Side note: Look at Aneesa. She was on Free Agents. She has been doing this ish for more than a decade).
16. Battle of the Seasons (2002)
In the show’s 1.0 incarnation (in other words, a time when the letters “C” and “T” had never been seen together on MTV), Battle of the Seasons was all you could have asked for: a simple RW/RR battle where the RR team destroyed the RW for much of the season, and then a team containing Challenge Champ Coral became victorious in the end.
15. Rivals II (2013)
The first Rivals was full of people who genuinely couldn’t stand each other (for the most part), which is why it ranks much higher. Rivals II featured a lot of well-I-guess-they-hate-each-other pairings, which made the tension way less dramatic. Bananas and Frank were paired up because of a Twitter war.
14. Battle of the Seasons (2012)
The second Battle Of The Seasons was unrelated to the first (hence no number in the title), which was a good thing in theory. The concept was solid — teams of four from an original Real World city season battling it out — but the casting was poor, which isn’t usually a problem for this show. Originally, a RW: Sydney team was cast, but was replaced at the last minute with a Fresh Meat mashup that contained Camila for some reason. Their unexplained absence, plus the unreasonably long stay of the RW: Saint Thomas team, produced a season lacking in Challenge mainstays that turned out…mostly boring.
13. The Inferno II (2005)
The Inferno II was the first installment after Road Rules was canceled. The Bad-Ass/Good Guys construct introduced was a cheesy, but necessary way of creating teams for the season. Despite a strong cast with “The Miz” in his prime, this season falls a few notches because of terrible, terrible host Dave Mirra.
12. The Inferno III (2007)
Kept the hokey Bad-Asses/Good Guys idea from Inferno II… and then put freakin’ Johnny Bananas on the Good Guys team (pictured). At that point, Bananas had only participated in The Duel (and was eliminated in the first episode), so we didn’t know what a full Bad Ass he could be but… come on Bunim-Murray. You knew. At least they knew to make CT a Bad Ass. He immediately lived up to the title by socking rookie Davis (off-camera) on the first night, resulting in his elimination before the game even started. He did this again on The Duel II, so CT also might not be very smart.
11. The Duel II (2009)
The Duel, a good format, was significantly lamer in its second installment thanks to a rag-tag crop of players. The field weakened on night one when CT annihilated Adam’s poor face and Adam fought back, ending both their runs. (And ugh, the CT-Shauvon hook up in front of Diem? Ugh. Ugh.). As for the girls, look at Rachel on that poster. How could she not win?! No contest. Bo-ring.
10. Free Agents (2014)
Free Agents seemed tailor-made to end the era of Bananas dominance in the Challenges: The elimination selections are random! Every man for himself! No alliances! But the reigning king of Modern Challenges has locked up his spot in the final, and the crop of contenders doesn’t look much different than it ever has. So much for that “anything can happen” tag line, eh?
9. Cutthroat (2010)
Cutthroat aimed to shake things up by having three teams instead of the usual two. The three worst players were team captains, which was interesting, but things didn’t get REALLY interesting until the 8th elimination round, when vets CT and Tina were brought in as beacons of Challenge godliness for the nominated players (Tori, Theresa, Tyler and Johnny Bananas) to defeat. The image of CT wearing Johnny Bananas like a backpack is worth $350,000 many times over. Cutthroat also was the first time a married couple (Brad and Tori) appeared — and won! — AND the show gave us the very weird, making-it-work-in-real-life coupling of Abe and Cara Maria.
8. Battle Of The Exes (2012)
OK, some of the exes were a bit of a stretch (did anything happen on camera ever between Bananas and Camila?) but a few were epic. Mark Long coming out of retirement to be paired up with Robin, who cried at literally everything that season, was one, but nothing topped the CT and Diem story. CT and Diem, actual exes with actual history and actual love between them, had a serious breakup and serious beef (she didn’t show at his murdered brother’s funeral) and they worked through it all on the show. Though they didn’t end up winning, watching them become friendly was extremely satisfying after nearly a decade of drama.
7. Fresh Meat II (2010)
Fresh Meat is important to the franchise because the cancellation of Road Rules reduced the pool of eligible players. But Fresh Meat II is important because it showed just how tangled the web of alliances is with these weirdoes. Kenny and Wes split the house, making all the other teams choose sides, and then, partially thanks to his insufferable arrogance, Wes’ alliance was slowly destroyed. When Ev, Wes’ last remaining ally, was eliminated, her reaction was so ridiculous. TJ actually quipped, “We’ve never had a four-year-old on this show before.” This Challenge also gave us Cara Maria, Laurel, Theresa, Brandon, Mandi and Vinny, so…. thanks?
6. The Gauntlet II (2006)
The Gauntlet II brought us the amazing TJ Lavin. TJ hates one thing more than anything else: quitters. Both Beth and Cameran quit in The Gauntlet II and TJ proved that he, weirdly, cares about this game perhaps more than the players when he let them absolutely have it. Also, letting people have it on Gauntlet II: Chicago alum Aneesa. “I don’t need a gauntlet, bitch. I will cut you with words.” Challenge gold.
5. Rivals (2011)
Rivals the first was genius because it featured serious enemies: Robin and Aneesa, Evan and Nehemiah, CT and Adam. But no one in Challenge history has ever hated each other more than Wes and Kenny, and they were teammates. While the redemption arcs were fun to watch — Paula got her first win thanks to nemesis Ev, CT’s constant badgering of “are you my friend yet” to his former punching-bag Adam finally netted him a yes — Jenn noted going into the final that Wes and Kenny were the only duo that never became a team. Their rivalry was that deep, and it cost them the win.
4. The Gauntlet III (2008)
Who doesn’t love a good underdog story? The Gauntlet III once again faced Rookies off with Veterans, and the Veterans dominated nearly every challenge. Until the final. Politics finally bit the mob back, as they’d protected their Vet teammate “Big Easy” throughout the Challenge because…well…they liked him. He didn’t have enough gas to complete the final and cost his entire team the victory. The catchphrase, “I don’t want another ‘Big Easy’ situation” lives on to this day.
3. Fresh Meat (2006)
Fresh Meat saved the show. Desperate for new people with actual athletic ability, Fresh Meat paired RW vets with random folks who auditioned and changed the whole game. Kenny, Evan, Big Easy, Evelyn, the absolutely terrible Casey, Ryan and Diem all came out of the original Fresh Meat crop, revitalizing game play and giving producers a well to draw on when another group of lunatics were due up. Bunim-Murray? It is almost definitely time for another Fresh Meat season.
2. The Duel (2006)
Crazy stuff happened on The Duel. Tiny rookie Svetlana beat monster vet Beth on a technicality in a one-on-one elimination and ended up the runner-up in the whole game. Tina, stone-cold sober and in broad daylight, punched Beth knowing she’d get sent home. She claimed, “It was worth it.” But the weirdest thing that happened on The Duel was that CT fell in love. He met Diem, who was coming back from her fight against ovarian cancer, and restored her confidence, made her feel beautiful, and showed a side of himself we’d never seen.
1. The Ruins (2009)*
We watch The Challenge for three main reasons. The Ruins perfected them all.
1. Love triangles. Before The Ruins, Wes was engaged to Johanna, who hooked up with Kenny, Wes’ arch nemesis, on The Island. Wes then came on the show with his new girlfriend, KellyAnne, who is the living worst. KellyAnne’s ex from her Real World season, Cohutta, was also on the show. KellyAnne and Wes went to live in the basement, where people would basically make appointments to come down and yell at them. It was a beautiful train wreck.
2. Fights. Three players were eliminated outside of gameplay on this season: Tonya when she smacked Veronica, and Brad and Darrell when they beat the crap out of each other for no reason because they are actually good friends. Also, when Ev’s best friend, the awful KellyAnne, was voted into the elimination round to face her BFF, Wes and Ev tore through the house smashing lamps and yelling in nearly everyone’s face.
3. Antics. In the actual elimination between KellyAnne and Ev, Ev gave up because she couldn’t face her bestie, earning TJ’s wrath. The Ruins managed to cast a stellar mix of old school and new school cast mates, and that caused drama in and of itself — vet Veronica thought sleeping with New Mob Leader Evan would score her a ride to the final, which it didn’t; the Champion boys continually lied to old-timer Syrus so he would have to go into elimination rounds and not them. SHAUVON POPPED HER IMPLANT. The crowning jewel in The Ruins’ never-ending escalation of lunacy was that the in-house drama got so bad that real-life drama came into play: Johanna actually threatened that if Wes threw challenges and cost her money, she would sell the house they owned together, which was in her name, and keep all the money. If The Challenge is a battle of the crazies, The Ruins is the champion in every sense.
*The Ruins was a perfect season of this show, but it is marred by reports after filming wrapped that Kenny and Evan allegedly violated Tonya while she was intoxicated. MTV settled this suit out of court. The rankings just reflect the show itself, but obviously Kenny and Evan’s alleged actions are deplorable.