How to Win at The Challenge and Life: A Champion's Guide to Eliminating Obstacles, Winning Friends, and Making That Money

by Sydney Bucksbaum

You’ve seen the rivalries. You’ve witnessed the blood, sweat, and tears. You’ve celebrated the champions. But what does it really take to win MTV’s The Challenge ? And what happens after the cameras stop rolling?

Since 1998, MTV’s The Challenge has tested competitors’ physical, mental, and emotional endurance. Some go on to become Challenge legends, going down in history as players who changed the game forever. But for each champion, there are dozens more who try and fail (over and over again) to earn the title.

In her time covering the show, pop culture journalist and Challenge superfan Sydney Bucksbaum has gotten to know many of the champs, gaining an insider’s knowl­edge of what goes into making a winning strategy—and how difficult it is to actually pull it off. Here, she profiles twenty-one of the most popular, successful, and infamous champions and reveals not only how they won The Chal­lenge but also how they applied the skills they learned from the experience to their personal lives and careers.

From seven-time winner Johnny “Bananas” Deve­nanzio, Challenge “Godfather” Mark Long, OG champ Veronica Portillo, elimination beast Emily Schromm to most-improved competitors Cara Maria Sorbello and Chris “C.T.” Tamburello, the best in the game look back at their decades of hard work, including the euphoric highs, devastating lows, and everything in between.

Eye-opening and inspiring, How to Win at The Challenge and Life is the must-have book for any and all fans looking to level up their own lives—and learn never-before-heard stories from the people who have dominated the show in every way.

Genres: Nonfiction, Self Help, Sports, Audiobook, Memoir

256 pages, Paperback

Published September 3, 2024

Reviews

[Mehva · Rating 4 out of 5]

Enjoyed this book about the Challenge. I have been watching the show for about 10 years so many I was familiar with but many others predated me. I missed some major players, Wes in particular who so influenced many seasons, Kaycee a more recent winner, Tori , Diem who showed up what courage grit were all about and others who maybe didn't win but affected the show alot. If you are a fan, you will probably enjoy this book.

[Jenn Adams · Rating 5 out of 5]

Rating based on purely my enjoyment of the content. I think when it comes to The Challenge there is a niche group of people who are Super Fans and then a lot of people who just don't care at all - so I'm not sure how large the audience will be for this book, but I'm glad I was able to snag an ARC.

There wasn't a ton of additional content here that you couldn't read in articles online, but I liked: the fact that the author did actual interviews with each particular champion; the way it was organized by number of wins; the length of each section felt right. (Honorable Mention to the fact that the Johnny Bananas Backpack elimination was talked about thrice)

Some of my faves (Wes and Ev) weren't in here and the absence of Ashley Millionaire Mitchell was noticeable as well, but I presume the author couldn't get everyone to agree to be a part of the book and I appreciate that the focus remained on those who were personally interviewed instead of sourcing from outside content just for a bulkier selection.

Very biased review because I <3 The Challenge... but thanks to Edelweiss and the publisher for this eARC in exchange for my honest review.

[Tina Loves To Read · Rating 4 out of 5]

This is a Non-Fiction book. This book is about the main people on the TV Show The Challenge. I have watched the Challenge for years. I really enjoyed learning more about some of my favorite people that have been on the Challenge. I do not think this is going to be for everyone, and I really feel you need to like the Challenge TV show to really enjoy this book. I felt the writing in this book was very good. I was kindly provided an e-copy of this book by the publisher (MTV Books) or author (Sydney Bucksbaum) via NetGalley, so I can give an honest review about how I feel about this book. I want to send a big Thank you to them for that.

[Holly | Raise Your Words · Rating 4 out of 5]

-- 4/5 Stars -- ★★★★☆​

Trigger Warnings for How to Win at The Challenge and Life: Failure, cancer, humiliation, death

How to Win at The Challenge and Life: A Champions Guide to Eliminating Obstacles, Winning Friends, and Making that Money is a nonfiction piece by Sydney Bucksbaum that has one of the longest titles I have ever seen (lol). Bucksbaum interviews multiple winners from the MTV show The Challenge deciphering how they, in fact, became champions of the beloved show.

Plot twist: I'm obsessed with The Challenge - we're talking to guilty pleasure, comfort show levels. When I saw that a book was written about The Challenge, it was immediately in my Amazon cart. That being said, this book was just okay. Bucksbaum gets a huge lift due to the subject matter (guilty as charged), but How to Win at The Challenge and Life really was just a series of interviews with previous winners. I loved hearing about their experiences from their points of view, but it really was just a printed and bound version of multiple blog entries.

All of this being said, I love The Challenge. If this was a different topic, I likely would not have finished this book... but gosh just reliving the Bananas Backpack moment alone brought my final total to 4 out of 5 stars.

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[Daniel Shelley · Rating 5 out of 5]

This is a fun little read if you're a fan of MTV's The challenge (formally Real World Road Rules Challenge). It's just interviews with 21 former winners of the show and provides insight on what the show and winning meant to them. I loved the variety of winners we got, but was definitely missing a few, Sarah, Evelyn, Paula, Laurel and Millionaire Mitchel. I would recommend to any fan, it's a quick read and is written by a reputable source.

[OutlawPoet · Rating 4 out of 5]

My kid and I are relatively recent Challenge watchers – I’ve seen maybe six or seven seasons (sprinkled out, not consecutive). She’s seen three, one regular, one All Stars and USA.

We’re blown away by how honestly badass some of these competitors are and this book was a nice little intro into some of the truly iconic ones. Now, not all the icons are represtented here – there were a few missing that surprised me – but I especially enjoyed learniing about some of the true OG Challenge stars. Honestly, my first experience with some of these folks was during All Stars – and now I know why they were asked back.

The stories aren’t always pretty, but they are inspirational – and I loved the little behind the scenes challenge details the book includes.

The ‘self help’ portion of the book was kind of shallow. I mean it’s mostly just never quit, keep your focus, and give 200% every day. But to be honest, I didn’t read the book for that anyway – I just wanted to know a little more about the people.

A good read – definitely a must for any Challenge Fan – even if you’re sort of a casual like me.

• ARC via Net Galley

[Chelé-----4 The Love of Books · Rating 5 out of 5]

I am a TOTAL "The Challenge" nerd!! I haven't missed an episode since it premiered in 1998 (also The Real World since 1992 & Road Rules since 1995)
so when I was gifted the ARC of How to Win at The Challenge and Life: A Champion's Guide to Eliminating Obstacles, Winning Friends, and Making That Money I was super excited! This is a great read and it was fun catching up with challengers I haven't seen in years and getting more insight into my favorite challenge champs!


Some of my personal favorite memories over the years are when Diem was going through chemo and took her wig off on camera for the first time, when CT (my favorite) wore Johnny (who I hate and sadly share a birthday with) like a backpack and dragged him across the elimination floor 🤣🤣🤣 and when Derrick came back as a mercenary on "Vendetta" and lasted 8 rounds to victory against Joss. I always root for the OGs


If you're someone like me who has followed and loved the challenge since its inception you'll really enjoy the stories, the journey and reminiscing about all things champ related!

[Chelsey (a_novel_idea11) · Rating 5 out of 5]

Well researched, laid out perfectly, and insightful this book is perfect for any fan of MTV’s The Challenge. I’ve been a fan for a long time and while I haven’t been able to keep up in several years, it was so fun reliving iconic moments and remembering favorites from earlier seasons. There were a few champions I couldn’t exactly recall but I still appreciated their chapters and insight. Some of the advice and memories were a bit repetitive but that’s to be expected. I also loved gaining insight into how people were casted, the invite process, and how authentic the show and winning truly seems to be.

[Sally Hand · Rating 3 out of 5]

I love the challenge 5ever. I mean it’s my wifi password? I watched 25 seasons in like 4 months so slay me? This book warmed my lil heart because I LoVe this show but the writing was pretty repetitive and I wanted more of that behind the scenes dirt. I get it tho because author is a journalist and some of the writing was def in the way we were taught (hello I’m a journalism minor) but it doesn’t lend itself well to the written werd in novel form.
xoxo
CTs biggest fan

[Erica Chaillot · Rating 3 out of 5]

This book was a carryover read from 2022. I enjoyed the interesting tidbits on some of the Challenge Stars. There were some notably missing players. It was personally a book I was intrigued about, so I wanted to read it after being a long term fan of the show.

[Nicki Nicksic · Rating 1 out of 5]

This show has always been a guilty pleasure. I just now feel guilty for reading this book. No hot goss, didn’t even include some characters, and how many times can one book use the word adapt when the topic has nothing to do with real life?

[Bella · Rating 3 out of 5]

When I saw that someone had made a book about the challenge I was stocked. As an OG fan of the challenge I enjoyed getting the chance to learn some behind the scene information and get a glimpse into the player’s experience while on the show.

I do wish that the book would have been longer and included more champions such as Wes, Jodi, Evelyn, Abe, Susie, Paula, Laurel, Ashley, Jenny, Jenna, Zack, and Kaycee would have been included. As it would have been great to read their stories and hear their prospectives on what it takes to be a champion.

[Adrie · Rating 1 out of 5]

I'm a lifelong Challenge fan, from the early early days when it wasn't called The Challenge. I witnessed the Julie/Veronica safety line debacle, the Bananas Backpack and Katie beating a mattress with a plunger, which is still one of my most favorite moments. I was so excited for this book, but I regret that excitement. This read like a badly written term paper that never should've been turned in. Like the roughest of rough drafts. I enjoyed some of the chapters (Landon, Darrell, Cara Maria, Emily S, CT, a small amount of Bananas) and anecdotes from the other players, but my god were the transitions and supporting text hard to get through. 9/10 do not recommend purchasing. Check this out at the library.

[Amy · Rating 4 out of 5]

I’ve been a huge fan of The Challenge since the beginning so I knew this book would be a lot of fun for me. If you’ve never watched the show this isn’t the book for you, it was more about revisiting old seasons and cast members than any true self help strategies but I didn’t care because I didn’t read it for that anyway. I was here for the awesome cast interviews and behind the scenes tidbits and it delivered on that front for sure. The format was great, each chapter focused on a winner and had interviews with them where they discussed iconic moments from their seasons as well as what techniques and strategies they used to get to the end. Overall a really entertaining and nostalgic read for die hard The Challenge fans!

If you’re also a fan of the show what is your favorite iconic moment? I’ll never get over the Banana Backpack 😂

[Irving · Rating 5 out of 5]

This is not usually the type of book that I read, but I’ve been watching The Challenge for 16 years, so of course I was happy to support the author and read more about some of my favourite challengers! Being a die hard fan who not only watches the seasons (sometimes multiple times) but also reads any and all articles and listens to podcasts about it, I know A LOT when it comes to this show, but I still learned a few things reading this book, and got some great quotes and advice from it. Definitely not a book for everyone, but a most for any fans of the show! 4.5 stars

[Paul Shailor · Rating 4 out of 5]

Very solid history of the challenge told by the winners. Each chapter does a good job of talking about the facts and with the cast members revealing some things I had never heard. Alton, Landon and Hunter's chapters were definitely my favorite with the majority of others being good. Derrick's chapter was probably the worse, he doesn't even mention Kenny, diem gets a sentence, and the joss elimination got two full pages. He said nothing interesting. Also CT's chapter was a bit of a letdown since all his quotes are from other sources and not from being interviewed for the book.

Sydney definitely knows her stuff though and clearly is a fan of the show. It was a really light and fun read. Most chapters are about ten pages and just go incredibly fast.

If you are a fan of the challenge this is definitely worth reading.

[Lauryn Smith]

this was the perfect audiobook to fuel my challenge obsession while commuting this week (feat interviews from some of the best champs!)

[Kira Holm · Rating 4 out of 5]

If you are a lifelong challenge fan, this book is a quick and interesting read!

[Jennifer · Rating 3 out of 5]

I can’t lie, I am a super-fan of MTV’s The Challenge (originally known as The Real World Road Rules Challenge) and have watched every season since the beginning, even after I stopped watching The Real World long ago. Should I be embarrassed to admit this, and to admit that I read this book? Maybe. 😂 But I don’t believe in feeling guilty about what other people might call guilty pleasures, so what the heck.

This book is essentially a series of interviews with people who have won The Challenge about their experiences on the show, presented in orderfrom least wins to most wins, though it certainly does not include everyone who has won including some multiple time winners - presumably it’s just whoever agreed to speak to the author. Because each chapter is just a write up of that person’s interview, this doesn’t really read like a book, nor is the writing itself anything special. Instead, it kinda reads more like you’re reading interviews with these people on a fan website. Indeed, the author, in addition to clearly being a Challenge super-fan, apparently has covered The Challenge for years on Entertainment Weekly’s website.

That being said, I did enjoy reading what the players had to say. Definitely a book for super-fans only though. And frankly I would not have spent money on it, but since I got it for free from Netgalley, I was happy to read it.

[Matthew Mutarelli · Rating 5 out of 5]

If you are a fan of “The Challenge” you will really enjoy this book.

There are a few notable folks not included, but maybe an opportunity for another one???

It gives a good look at some of the champions of the challenge from their challenge life and their personal life!

Also brings back some of the best moments in the challenge - Bananas Backpack, Julie and Veronica on the cables, etc.

Fun read for the fans!

[Christopher Honthy · Rating 5 out of 5]

How to Win at The Challenge and Life by Sydney Bucksbaum is the perfect read for anyone as infatuated with The Challenge as I am. As someone who’s watched nearly every season (minus the ones lost to time or licensing), this book felt like a well-earned deep dive into the stories behind some of the show’s most iconic champions.

Even though the book came out fairly recently in 2022, it’s already a little outdated—especially with Jordan Wiseley, my favorite champion, racking up two more finals wins since then, bringing him to five total. That aside, most of the featured competitors’ stats have stayed the same, and the book still serves as a solid snapshot of their careers at that moment.

That said, I wish the scope had been a bit wider. While the book shines a light on several notable players, it would’ve been great to include more champs, especially those who defined earlier eras or had dominant runs. Turbo, for example, won arguably the hardest final the show has ever seen. Paula, Sarah, and Evelyn—who’s hands down one of the most dominant women in Challenge history—deserved mentions. And even competitors like Camila, Kenny, and Evan, who are now banned from the franchise, had undeniable impacts on the show’s legacy. Kenny alone made the final in 7 of his 8 seasons and walked away with two wins—he’s one of the best to ever do it.

Still, I loved this book. Hearing from legends like CT (an absolute menace in the best way), Landon (an all-time favorite I hope we see again), and Johnny (whose perspective made me respect him a bit more) made for a really enjoyable and nostalgic read. And Jordan? He’s the best competitor we’ve ever seen—mentally, physically, and strategically.

This book is a must-read for Challenge diehards. It may not cover everyone, but it delivers a great mix of insight, stories, and appreciation for what makes The Challenge such a uniquely intense and addictive reality competition.

[Rosario Cook · Rating 5 out of 5]

If you are a die hard Challenge fan like myself, this is a must read book. Sydney Bucksbaum has done a great job delivering a book that goes behind the scenes of the iconic competition reality show and provides the reader with first hand knowledge from past winners.

This is a short audiobook (only a little over 6 hours) and it’s broken down by sections based on number of Challenge wins from one win (Julie Rogers aka “The Murdering Mormon”) to seven wins (Johnny Bananas). Each section has a chapter dedicated to all winners who fall into that category and goes through the winner’s Challenge career and how they approached each season they were on. The reader is provided with what motivates each winner and also their highs and lows throughout their time on the show.

I was a late fan of The Challenge and did not start watching it until the summer of 2023. At that point, I binge-watched seasons 10 to 37 (seasons 1 to 9 aren’t available in Canada) in a span of six months. Therefore my Challenge fan knowledge is really strong and the only thing that surpasses it is my devotion to Chris “CT” Tamburello (the only entry in the five wins section of the book). This book was on point with every event that has occurred on the show. It also does not shy from asking the former winners about some of the more controversial occurrences over the years (ie. Emily Schrom in Exes 1 and Jordan Wiseley’s insult to Jemmye on Dirty 30).

This is a book I will likely go back and listen to for years to come!!

[Emily Burch · Rating 4 out of 5]

Thank you to Atria Books and MTV Books for the ARC in exchange for an honest review. I am a superfan of The Challenge ever since I started watching as a teen, and I was so excited when I learned that there was a book coming out about it (so obviously, I JUMPED on the chance to get the ARC).

The book takes the format of a series of brief interviews with a selection of The Challenge Greats. It's divided into sections based on number of wins (interviews with one-time winners come first, for example). Some of the names will likely be more familiar than others to a lot of more casual fans, but some of the biggest names are also involved (Johnny Bananas, Cara Maria, C.T., etc.).

At its core, the book is a quick, easy read. A bit of a fluff piece, the content is pretty similar to what you'd find in a well thought out interview and article about each of the champs. It's not a behind the scenes tell all, and it's not meant to be. And of course, since it's based on interviews, there are several notable absences of Challenge greats (who I assume were not able and/or willing to participate). Still, I quite enjoyed the read.

[Severina · Rating 3 out of 5]

I am an avid fan of The Challenge, especially its latest iterations of the last 10 or so seasons. I love the competitiveness, the wild challenges, the amazing contestants. I was super excited to get this book. I was hoping for a lot of behind the scenes stories, some hot goss, and maybe what the book promised in its title, a bit of a self-help guide to finding success. Instead, it’s a pretty generic series of 4 or 5 page short interviews with a variety of Challenge champs. In fact, for CT’s chapter he clearly didn’t want to participate and the author had to use snippets of past interviews and things he’s said on the show. And yes, the champs gave their reasons why they thought they won (some examples: be aware of your surroundings,support your partners, don’t be afraid to fail) but there’s no attempt by the author to tie these rather cliched soundbites together into any kind of self-help lesson.

On the plus side, thank you to Darrell for actually spilling the beans on some fun sneaky shenanigans from your season, and to Landon for being every bit the awesome person everyone online says you are.

[Sandy Dallabrida Hagy · Rating 3 out of 5]

I don't know what I was expecting from this book but it wasn't this. To be fair, the title says what it is and it is what the title says. It is full of self-help-like advice about winning and being your best self and overcoming obstacles and it's told through the eyes of The Challenge. If you're a fan of the show, it's a quick read and it's kind of interesting. However, there's no new material covered here. If you follow The Challenge, follow the competitors on social media, listen to Challenge podcasts, read Challenge interviews, there's not really anything new you will take out of it. The quotes in the book almost seem like they are actually taken from interviews and podcasts and other media points over the years instead of coming together like any kind of cohesive interview. I'm not saying the author didn't interview the contestants named in the book, but what's there is just not that deep. It was a quick read on New Year's Day. It'd probably be something good to take on the beach if you were looking for this kind of content. It's not deep and don't expect it to be.

[PJ · Rating 4 out of 5]

This book is a love letter to The Challenge written by an author who is clearly as obsessed with the show as those who choose to read this book are. It is nostalgic and endearing, but does not reveal anything the average superfan doesn't already know. Again, it's a love letter, not a biography. The chapters I enjoyed the most surprised me, and the enjoyment of this book is further supported by the success of the All Stars franchise. I was disappointed that the C.T. chapter did not contain an interview with him, but that is not a knock against the author. Overall, if you love The Challenge and want to hear directly from the champs about why they love The Challenge, too, then it's a great, quick, easy read. If you want a tell-all, peek behind the curtain, or a look at some of the biggest controversies around the show, hopefully one day we'll get something like that in some form of media.

[Laura · Rating 3 out of 5]

This book details the stories of 1 time winners all the way to Johnny Bananas 7 wins. It's cool to hear the stories of each player as they share their thought processes on their seasons of The Challenge to how The Challenge lessons have worked for them in their day to day lives.
it seems that for many, once in The Challenge then you are in The Challenge for life. I guess the ability to show that you still have it as you age, the thrill you get in trying to outmaneuver your teammates and the physicality are reasons to keep your prospects open and to not retire, though a few do.
Since I watch the show it was interesting to read about the struggles that each person has faced and how they have overcome them to be the best they can be. After reading this book I expect a few to be continuing this show until well into their 50's if they can get away with that.

[caitlin king · Rating 3 out of 5]

I was so excited to see this book available on NetGalley! Since I’m a huge fan of The Challenge and an avid reader, this felt like the perfect fit for me! However, this didn’t quite land with me as I’d hoped. It was a fast read and a fun time, but it wasn’t as much of a deep dive with behind-the-scenes stories as I’d hoped.

The book is a combination of MTV’s The Challenge champion profiles, grouped by number of wins. I did like the variety of champions included and appreciated that the appearances on The Challenge All-Star and Champs vs. Stars spin-offs were mentioned. Overall, it read like a combination of magazine features about each champion. It only scratched the surface and recycled a lot of previous interview content. The writing style wasn’t compelling and lacked depth. I was also expecting more content about how the show is made, but that was minimal. Any book about The Challenge is going to be lacking if there isn’t much about TJ or his role as host. He is a strong part of the show and how it has evolved to where it is today so that was a real missed opportunity in my opinion.

I would not describe this book as “eye-opening” since most of the content wasn’t new or attention grabbing. There wasn’t much included that I hadn’t heard or read through other sources already. The profile of C.T. was my least favorite of the bunch. It was mainly quotes from other articles already written so that was a letdown. I would have preferred it to have been cut from the book and replaced with a profile of another champion who wanted to participate directly in this project. The profile on Syrus was the most interesting. He’s had a long career on The Challenge and has really evolved. You could really get a sense of his growth both on the show and in his personal life.

I’m glad I read this and would consider it “required reading” for any die-hard fan of MTV’s The Challenge.

[Jessica Smith · Rating 3 out of 5]

I love the challenge. I have watched many seasons multiple times. I like following the cast mates. So when I saw this book, I was super excited. Clearly this is a niche book for fans of the franchise, but I enjoyed reading it.

My biggest critique is where is the Wes chapter? He won 3 seasons, was a finalist in like 5 others and is tied for the most elimination wins in a single season. Not too also mention the character Wes is outside of the challenge, the influence. He is mentioned so many times in the book in other people’s segments. Why snub him?


Lastly I rated 3 stars because no Wes and because no real new information. Just kind of more of what I’ve seen or known. I did enjoy the interviews and giving the challengers the spotlight.

[Sarah &#x1f33a; Books in Their Natural Habitat · Rating 3 out of 5]

I’ve been a fan of The Challenge all the way back to the Real World/Road Rules days. In fact, I’ve watched the show long enough now to watch many of the cast members grow up, have families, and venture into acting, their own businesses, etc.

How to Win at the Challenge and Life is an inside look at past Challenge winners… how did they come to be on the show, their attitudes, what they learned, and how it’s changed them. What you see on tv is often an edited version, and I loved getting the full story of some of the elimination challenges I remember the most. Bananas backpack anyone?

Overall, I loved this insider’s perspective to one of my longstanding favorite tv shows and the people I root for and even those I love to hate!

Thanks to @netgalley for the complimentary copy. The review expresses my own personal opinions.