Real World: Boston #8: No one cares about Road Rules


As I’ve been working on this project, I’ve asked anyone who will listen to name their favorite season of The Real World. The answers have included the usual suspects, mostly Seattle with a handful of surrounding seasons, including New Orleans and Boston (I’d hope so!). What I haven’t asked is for people’s favorite season of Road Rules, and I can’t imagine I’d get any answers, either, because, of the two, Road Rules is clearly the inferior show.

Road Rules launched in 1995 with the basic premise of Real World on an RV, and like most spin-offs, it pales in comparison to the original. Real World seasons are iconic, with memorable “characters” and infamous moments; Road Rules seasons are a series of reality show challenges. Arguably, the show is better known as a component part of The Challenge (fka Road Rules: All Stars and Real World/Road Rules Challenge), a competition-based show that seemingly was created to piggyback off the success of Survivor.

While the shows briefly crossed-over in 1996 (the second season cast posed as housekeepers and successfully stole the eight-ball off Miami’s pool table), the first foray into a Challenge-styled competition came — you guessed it — in 1997.


At the after-school program, the Boston housemates are told that they’ll be setting up a video pen-pal program — in San Juan, Puerto Rico. Previous seasons had featured such trips, but perhaps none with logic so specious. Kameelah, Genesis and Montana react like they won the Showcase Showdown; spoiled little Elka pouts about not going to Europe, where she’s be able to visit her boyfriend. Their goals are simple: Syrus is hoping for women, nice weather and cheap rum; Genesis wants a tan; Kameelah hopes for no arguments; and Montana somewhat facetiously wishes for a cockfight.

The housemates decamp to San Juan’s Gallery Inn, which is covered in death-mask-like sculptures; Jason describes the place as “Salvador Dali’s cottage in the woods.” The trip is the first time everyone had been out of the firehouse together, and the bonding starts at a club, and it goes better than their time at the Puerto Rican after-school program, because only Kameelah and Elka speak Spanish. Still, with their CU-SeeMe set up, the housemates can get back to vacation.

Montana goes on a date, Jason’s freestyle poetry is met by Syrus’ surprise talent for spitting dancehall flows; the group goes on a boat ride to the party beach and unwind with a dinner party. While Montana, Sean and Kameelah discuss affirmative action, Genesis excuses herself; again, she feels stupid when the group has these conversations. “I think you’re being far too intense, all of you,” offers Jan, the innkeeper. Montana explains that they’ve all had a lot happen to them, but Jan isn’t buying it. “Yeah, but life keeps going on — you just keep doing it.” Sage advice that the barely-adult housemates don’t quite heed.


However, Real World: Boston isn’t the only MTV crew in Puerto Rico: the cast of Road Rules: Islands is there as well. Coincidentally, I actually remember this cast because one of them, Vince, is from my hometown, Boca Raton. At this point, Boca was best known in pop culture as the home of Jerry’s parents on Seinfeld; it would be about five years before Boca’s Chris Carrabba would become an emo demi-god. Vince getting chosen for the show was covered in the local paper (the one I’d write for in high school), and I’m sure I watched because of the local connection. It wouldn’t be until high school that Vince’s background (private school, gated community in Boca’s city limits) would cause me to see him as an adversarial Other (public school, “across the tracks” in West Boca).

But aside from the hometown connection, I don’t remember much about this season of Road Rules, or even what would happen next. In the two-episode Real World – Road Rules Challenge crossover, the Road Rules crew are given dossiers about their Boston counterparts: Kameelah is “not shy about telling it as she sees it;” Montana is an “unabashed, unshaven feminist;” Jason is (hilariously) equal parts Kerouac, Beck and Bukowski with an eyeliner pencil. They scribble some trash talk on an invitation to a competition and leave it with the Inn before Boston arrives (like a comic book crossover, exactly when this “event” takes place in continuity is unclear).

When the housemates get the message with the Road Rules logo, the girls freak out like they did when they found out about the trip. They ponder the meanings of the pun-heavy trash-talk; Sean assumes “some gay guy” is behind a joke about “rolling his log.” The next day, the housemates head to the woods to meet Road Rules: apart from Vince, there’s the cocky Jake, the cast pariah Oscar, and Kalle and Erika, whose main characterizations (in these episodes, at least) are that one is blonde and one is brunette.


At this point in Road Rules, competitions provide the cast’s only way of making money for living expenses; they have $14 to their names and need a win badly. But they’re confident at their chances: they’ve been on the road and sea, while the housemates have had the relatively cushy Real World experience. “What happens when you pick seven strangers, put them in a house, and they make total and complete assholes out of themselves,” jokes Vince.

Over two episodes, the teams compete in a series of team-building physical challenges; the first four games are worth $50 a pop, with $100 for the final game. With their seven people to Road Rules’ five, two Real Worlders will be randomly removed from each game for a little extra drama. The Road Rulers are mostly worried about college basketballer Syrus, who is shown in slo-mo with bigfoot sound effects (problematic!). Syrus knows what’s expected of him, pushing himself to the point of injury: he underestimates a jump and busts his shin open, but bandages it and continues.

Real World jumps to a 3-0 lead; it appears that their forced-bonding is starting to pay-off. Meanwhile, the crews start to mingle. The Road Rulers are whining about needing the money; Jake is blathering on about love, affirmation and group sex with the Real World women, while Oscar and Syrus bond over their respective outcast statuses. (According to a bit of “trivia” on Wiki, the cast asked producers to replace Oscar with someone they liked, but because he hadn’t actually done anything wrong, “production chastised the cast for their negative and isolating attitude.”)


Road Rules wins the final two events, tying in money but losing in points. Their “severe humiliation” for the latter is giving pedicures to the housemates. True to their established roles, the chauvinistic Oscar refuses to give Montana a pedicure (as if giving a man one would be better for him?), and Montana takes offense, rubbing mud in his face before the two wrestle with each other.

After the challenge, Syrus attends to his leg wound and the two crews meet at a club. Sean hits it off with Erika, who wonders “When’s the next time I’ll be in Puerto Rico partying with the Real World?” Apparently, “I’m on the Real World” does work as a pick-up line, even to other reality show-ers. The morning after, Sean gets teased for hooking up with Erika. Jason won’t confirm or deny the “rumors” of what happened, while Montana jokes that the two “macked down” at the bar and that Sean had Erika up against the wall in the bathroom. For his part, Sean is ever the gentlemen, coyly no-commenting the situation.

Whatever actually happened between Sean and Erika aside, it wouldn’t be Sean’s last romantic encounter on a Road Rules spin-off. The next year, he’d be a part of the inaugural Road Rules: All Stars cast, alongside Eric from New York, Jon from Los Angeles, Cynthia from Miami, and Rachel from San Francisco — who is now his wife and mother of their seven (!) children. But that wouldn’t be for another couple of years. After this episode, Real World returns to Boston, and Road Rules continues down the road to obscurity.


Best Music: Third Eye Blind deep cut ‘London’ soundtracks the housemates’ boat ride. Coincidentally, a Third Eye Blind song is at the center of my only Road Rules memory. In the show’s next season, the crew must film an anti-suicide PSA with the band’s ‘Jumper’ as the soundtrack. I can’t hear the song without thinking of that episode, which is streaming in full on YouTube (if only Real World was as accessible!).

It wasn’t just MTV shows: Third Eye Blind seemed to be the pop soundtrack for the late ‘90s; despite peaking at #25, the band’s self-titled debut spent two years on the charts and spawned five singles. Obviously, the meth-addled ‘Semi-Charmed Life’ was everywhere. ‘London’, along with ‘Graduate’, appear in the nostalgic essential Can’t Hardly Wait, and I imagine ‘How’s It Going To Be’ popped up somewhere. I never would have copped to liking them (way to pop at the time), but their music has definitely aged better than some of the shit I was listening to back then.

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