Best Three-Time Challengers

We’re come to a point in Challenge History where three-time competitors are still considered “rookies.” Look at Big T on Double Agents. She’s friends with all the new UK kids and distanced from most of the veterans. She’s not a complete newbie, but she hasn’t left a huge mark on the show yet.

Earlier in Challenge history, three seasons was plenty of time. Some really great competitors only appeared on three seasons, and they’re fondly remembered by Challenge fans.

This list is fairly subjective, but people who are successful on the show stand a better shot at getting featured. Individuals who appear in most episodes, win competitions, and win seasons will become more relevant. I’m trying to balance this with storylines, fights, relationships, and memorability. Further, anyone who appeared on Total Madness or Double Agents will not be featured. While anyone could come back, people on recent seasons are especially likely to continue their Challenge careers. Further, spin offs and Mercenary features are not factored into appearance totals, only formal Challenge appearances.

Honorable Mentions

15. Jamie Murray– Simply on here because he won 3 out of 3. In terms for relevant story lines, he really doesn’t have any.

14. Ibis Del Mar– She was basically a number in the X-treme alliance on The Gauntlet 2, which allowed her to win. Perhaps she’s best remembered for being duped by Veronica on The Ruins.

13. Natalie Negrotti– She was going to be a big name on the show, making the Final Reckoning final and having a showmance with Bananas. Then she threw some glitter.

12. MJ Garrett– MJ was a much bigger name on The Real World, but he won his first season and was the first person to be a two-time replacement.

11. Cara Zavalata– Won her first season, had some strong alliances and rivalries, but was a pretty bad competitor. She was a Playmate though.

10. Sylvia Elsrode

As a member of the Lavender Ladies, Sylvia’s role in Challenge notoriety is often overlooked but worthy of acknowledgement. On her first episode of The Challenge, she turned her back on her Real World: Skeletons alliance and voted Tony into elimination against Bruno. Nicole Z. was furious, saying that her new friends didn’t care about her. Nicole was wrong, and Sylvia would play the game with a strong alliance. She made it midway through Invasion, but her brief appearance on Vendettas resulted in a medical disqualification. Her shining moment was on Final Reckoning where she was paired with Joss. The duo was the only team to stay in the main house for the entire season. Some people will believe she deserved to win, but they might just be conspiracy theorists.

9. Ryan Knight

Sadly, Knight passed away in 2014 shortly after filming Battle of the Exes 2. While he wasn’t the strongest competitor, it was clear he was going to be one of the future stars of The Challenge. He was very connected with the “rookie revolution” and was strongly involved in the Challenge social scene. Rivals 2 was Knight’s strongest season, almost making the final, and he was the type of player who would survive in the game simply because he was friends with most people. Had he not passed away, Knight would certainly continue doing the show. Would he ever win? Perhaps not, but he thrived in the social environment and kept the house fun.

8. Eric Nies

There’s something to be said about being a true OG like Eric Nies. He was on the first Real World Season and the first Challenge season (Road Rules: All Stars). When The Real World was going to be included in competition show in the late 90’s, Eric Nies was the first name that would pop into many minds. As such, he was a leader on his seasons. He was valued on Battle of the Sexes until a disqualification nuked his score. Then, he brought his pet jump rope onto Battle of the Sexes 2 and stayed strong with his group of vets. He won that season, never to return to The Challenge again.

7. Jodi Weatherton

It’s a good thing Jodi didn’t stop with one season. Her time on The Inferno 2 was a mess, sparking a major fight when she voted Veronica into elimination then lost to her. On The Gauntlet 2, she was much stronger. Her solid alliance of Road Rules X-treme girls got her to the end, where she won. She also hooked up with half of the guys on the cast, but it was all good fun until she interfered with Mark and Robin’s relationship. She seemed more tame on The Duel, but she will forever be remembered as the winner of the first individual Challenge ever, and didn’t even face a single elimination.

6. Jillian Zoboroski

If her first season was her only season, Jillian wouldn’t be nearly as memorable. She really came alive on The Gauntlet 3 when she didn’t have her Road Rules: X-treme alliance. She started dating Frank and won three eliminations on her team. She found herself on a losing team, but ended up winning thanks to Big Easy’s disqualification. After another brief hiatus, Jill returned on Fresh Meat 2. Along with Pete, she won two Exiles and had to navigate a dicy social game. She aligned with Kenny and made it to her second final, but only came in third.

5. Emily Schromm

Coming into the game strong, Emily was one of the few people from Real World: DC who ever did a Challenge. Immediately she became recognized for her relationship with Ty and her fearless demeanor. This allowed her to get to the end of Cutthroat, but both of these things got her an appearance on Battle of the Exes with Ty. On this season, she may have been the most feared girl in the game. She won three eliminations, saw the final, but came in third. On Rivals 2 she got the perfect partner with Paula, which allowed the girls to win the final. Not only is she a Champ, Emily is one of those rare competitors who has never lost an elimination.

4. Frank Sweeney

Winning your first season is a major accomplishment, and it set the tone for Frank on The Challenge. He was quick to become a leader, despite his lack of experience. Though he had emotional outbursts, he was just as intense in competitions. His pairing with Bananas on Rivals 2 was questionable, but merged the “rookie revolution” with the old school allies. Frank was going into Free Agents strong, but a sickness took him out of the game. While he didn’t last long that season, he has technically never lost an elimination.

3. Emily Bailey

At one point in time, Veronica said: “The game used to play me. Now I play the game.” In this quote, “the game” is Emily Bailey. The Road Rules alumnae got her start on The Extreme Challenge, and while she was never one to shy away from confrontation, she was fairly tame. On Battle of the Seasons, she played a more aggressive game. She eliminated Veronica & Yes because they right outside of the Inner Circle, viewing her teammates as threats instead of assets. This created a toxic environment on team Road Rules, but it allowed Emily to advance. This attitude was continued onto Battle of the Sexes when she targeted the more athletic and popular girls. Aneesa, Rachel, and Veronica all went home because of Emily’s antics. She basically had a ticket to the final until she quit when her boyfriend James went home.

2. Kina Dean

Of all the Rookies to win a Challenge season, fans seem to hold Kina in the highest regards. Perhaps this is because she improved so much between her first two seasons. She was one of the first girls eliminated on Battle of the Sexes 2, but she proved her worth on The Gauntlet 2. She had to fight to the end, as the team captains were sent into The Gauntlet every day their teams lost. However, Kina survived all of the eliminations and won the final in the end. Her appearance on The Duel was less impressive, losing to Svetlana in Push Me. Still, her appearance on The Gauntlet 2 seems to define her legacy and demonstrate her abilities as a competitor.

1. Tori Hall

Coming into The Challenge as a Rookie on The Gauntlet 3, Tori quickly became known for her outspoken nature and relationship with Brad. She won an elimination that season, butted heads with Frank, and won the entire seasons. As we all know the Rookies weren’t the most worthy team of winners, so when she returned on The Duel 2 we got to see what she was truly made of. This time, she was half business and half Brad. The game put stress on the relationship, and Tori went home near the final. On Cutthroat, she found a way to balance the game and Brad. This time she “won” an elimination against Tina Theresa and won the entire season. Then Brad returned on Vendettas and Final Reckoning, and despite Tori not being on the shows, she became relevant again.