Big Brother has been a CBS phenomenon ever since the first season aired all the way back in the summer of 2000. If you’ve never watched Big Brother before, think Survivor but without the bugs, heat, and starvation. In order to do well in the challenges, Big Brother contestants must create an impeccable social game, have critical thinking skills, and have some athletic ability.
If you’re a Big Brother diehard fan, you’ve watched the game evolve into what it is today. Similar to Survivor, in the early seasons, there wasn’t a blueprint on how to play the game. As more and more seasons came out, students of the game were able to study, analyze, and replicate what they’ve learned into picture perfect strategy. Therefore, it’s no surprise that the majority of the ‘best’ winners of Big Brother came in the later seasons as more and more people figured out the best way to succeed.
Without further ado, let’s get into our rankings of the top ten Big Brother season winners of all time! One note that we want to mention is that these rankings only include contestants who have actually won the game. With that being said, please advise that spoilers are ahead!
10. Jackson Michie (Season 21)
Jackson Michie certainly drew a lot of criticism for his gameplay and comments that he made during the early days of season 21. He was accused of racism against houseguest, David Alexander, and according to Oprah Daily, was quoted saying things like “I want to mule kick him in the teeth” and “you’re not on Bravo or BET.” Michie then went on to target three minority cast members, including Alexander, in the very early stages of the game which also drew the ire of Big Brother viewers at home. The video below depicts some of the moments caught on camera and Jackson’s explanation afterwards:
Michie has since apologized and seems to have grown from his experience. Despite his shortcomings in the beginning, there’s no denying that Michie played a flawless game, strategically, throughout the course of the show. He excelled in the “golden boy” archetype by being incredible in HOH (head of household) and POV (power of veto) competitions and was always apart of the majority alliance in the house, known as “Gr8ful.” He also set a Big Brother record for most challenges won by a male in a single season, which was nine in total.
Michie was also able to start a “showmance” with fellow contestant Holly Allen, who also made it to the end with him. He ended up defeating Allen in the finals by a 6-3 vote to be crowned the winner of season 21.
His best move came at the final 5, when he was somehow able to convince Cliff Hogg and Nicole Anthony that Tommy Bracco was targeting them. This allowed him to save not only himself, but his showmance Holly as well. They were able to pick off Cliff and Nicole in the subsequent votes after that, and the rest is history.
9. Jun Song (Season 4)
Jun Song demonstrated one of the most effective ways to win the game in Big Brother, and that’s by perfecting what’s called the “floater” strategy. A floater strategy involves a conscious decision to join zero alliances, or many alliances, but not having loyalty whatsoever to any of them. Back in the early seasons, cast members preferred keeping people around that they liked or did things for them, and Song was especially good at cooking, which led to her being more desired to have in the house than other people. She knew this, and was able to exploit it to her advantage.
Song was also great at downplaying her own game, to the point where others perceived her as weak and not a threat to their own games. But by the end, she won with a commanding 6-1 decision over her ally, Allison Irwin, to take home the $500,000 grand prize.
Song’s placement on this list is due to her being the first winner to display the floater strategy and perfecting it. She essentially outlined the blueprint for future players that wanted to replicate this strategy, so she gets the credit here.
8. Hayden Moss (Season 12)
Hayden Moss could literally do no wrong during season 12 of Big Brother. He captured America’s heart by being good looking, charming, and playing the game the right way. While critics will say that he played a “boring, non-disruptive” game, that’s sometimes exactly the way that you have to play in order to win these types of competitions. He hardly had any blood on his heads (meaning he wasn’t directly responsible for the majority of the vote-offs). He also developed a showmance with Kristen Bitting and sailed by during the height of the “Brigade” alliance that he was a part of.
Not like it matters much, specifically when solely talking about Big Brother winner rankings, but Moss also placed 5th on his season of Survivor: Blood vs. Water, displaying the same game tactics he used on Big Brother and performing extremely well there. When someone is as talented and diverse as Moss is in his social gameplay, they certainly deserve a placement on this list.
7. Maggie Ausburn (Season 6)
If you’ve never seen Maggie Ausburn in season 6 of Big Brother, you missed out on the first time a person truly played the “villain” role and won the game.
It’s fair to say that when your alliance dubs themselves “The Good Guys” and names the alliance “Friendship,” there’s a pretty good chance that the people watching at home are going to turn against you. The “Friendship” alliance, that Ausburn helped lead, was often seen as volatile, cliquey, and abusive towards the other castmates. Viewers at home instead decided to root for the underdog alliance of the house as they were seen as the misfits of the house.
Ausburn deserves all the credit in the world for keeping such a dynamic, destructive alliance together. Her persuasion skills were literally off the chart and almost ruled the alliance with a cult-like mentality. Allying herself with many big personalities and targets, she perfected the “flying under the radar” strategy. After her narrow 4-3 win in the finals, she was quoted as saying: “I feel like a lot of my strategic moves were to not come out and be the aggressor, not be the person who shines so much, but try to blend in and maintain my competitive edge that I had.”
6. Nicole Franzel (Season 18)
Of the handful of players to have played Big Brother three times, Nicole Franzel’s finishing placements are clearly better than the rest. In season 16, which included one of the strongest Big Brother casts of all time, she placed seventh. She then went on to win season 18 with a 5-4 win over Paul Abrahamian. Finally, in season 22 during Big Brother: All Stars, she finished third. That is quite an impressive resumé over three separate appearances.
Franzel also has the record for most days spent inside of the Big Brother house with 255 days—that’s gotta stand for something! What’s most impressive about Franzel was that she was able to execute three different styles of gameplay throughout her Big Brother career: aggressive, flying under the radar, and being a part of a dominant alliance. Anyone that can be that well-versed and be tested in so many different situations and excel is certainly worth being in the conversations as the best of all time.
She was also known for having multiple showmances, which certainly aided her social gameplay and offered had protection from other players in the house. One fun fact about Franzel was that the person she’s married to now, Victor Arroyo, played on the same season with her in season 18, and he didn’t even vote for her to win in the end!
5. Andy Herren (Season 15)
Due to the very nature of the game, Big Brother requires you to have the ability to lie, bluff, and deceive your opponents at any given moment. Andy Herren might in fact be the nicest liar that the world has ever seen.
Just watch the following clip of Herren in action here, convincing Helen that he doesn’t know of anyone coming after her:
It’s almost second nature for Herren to casually reassure someone; his persuasive skills are off the charts!
He was responsible for so many of the shocking backstabs and blindsides during the eviction ceremonies, and yet still was in the good grace of the house. So much in fact that he didn’t receive a single vote for eviction throughout the entire tenure of the show. How is that even possible?
But another testament to Herren’s game was the fact that he knew at the final four that he was the biggest target left in the game, and took it upon himself to win the HOH at four and again in the final 3 to essentially secure his spot as the Big Brother winner. He just had too big of a resumé for the jury to ignore when all was said and done.
Herren ended up winning with a 7-2 vote at the the end of the show. Despite being perceived as a “rat” to some viewers at home, there’s no denying his dominant deceptive gameplay and social prowess.
4. Derrick Levasseur (Season 16)
It almost feels criminal to not have Derrick Levasseur listed in at least the final three spots, but with so much competition facing him, this is unfortunately where he’s going to fall.
Levasseur from day one had everyone wrapped around his finger, and it clearly showed as he is only one of six people all time to have never been nominated for eviction. He was a part of the alliances of “The Bomb Squad,” “Los Tres Amigos,” and “The Rationale.” He also had a final two deal with Cody Calafiore called “The Hitmen” and even had a secondary backup deal with Victoria Rafaeli. Even with all of these alliances and connections, no one suspected a thing and they thought Derrick was always with them.
Derrick’s charisma and gift of gab certainly served him well throughout the competition. He was even a part of the secret organization called “Team America” in which he had to perform secret missions for extra cash throughout the season decided by America’s vote at home. Check out the clip below of one of Derrick’s best scenes during season 15 so you can really get a grasp of how perceptual and intuitive he was throughout the game:
Would it surprise you if we told you that Levasseur was a police sergeant? Probably not, right? We certainly wouldn’t want to be interrogated by Derrick, that’s for sure!
3. Will Kirby (Season 2)
Big Brother may not be where it is today, or even here at all, if it weren’t for Dr. Will Kirby.
Kirby essentially wrote the playbook on how to play Big Brother, and is often compared to Richard Hatch of Survivor, being credited with realizing that the intellectual, strategic players can have a big advantage in the early versions of the game. It’s fair to say that Will Kirby was the first “puppet master” that the game had ever seen before.
Kirby knew that this was more of a game of psychological warfare than winning “meaningless” competitions. It sort of felt like you were watching the Big Brother version of American Psycho. He had a maniacal demeanor and sense of humor, and was often blunt in his assessments.
He went the entire game without winning a single HOH or POV challenge, making what he did even that more special. You have to respect how ahead of his time that Kirby actually was. He was in a league of his own, and it was put on full display during the final vote, in which he won by a vote of 5-2 over Nicole Shaffrich.
Rob Cesternino, best known for his Rob Has A Podcast show and competing on Survivor, claims he based his Survivor strategy entirely off of Will Kirby’s game in Big Brother.
19 years later, Kirby was honored during Big Brother season 22 by being the answer during a trivia question in the first ever triple eviction special. Everyone realizes how important he was to the success of the show and being responsible for where it is today.
Being an OG of Big Brother, considering the era in which he played where there wasn’t a textbook to study on how to play, he deserves placement on this list among the best to ever do it. Kirby even returned in Season 7 and despite having a massive target on his back, he was able to work his social magic and make it all the way to the final four before finally getting a lone vote to evict him from the Big Brother house.
2. Cody Calafiore (Season 22)
Here’s where the list can get a little dicey – most rankings won’t include Calafiore on them because they were published before season 22 aired on CBS. But, with how Calafiore played in the most recent all-star season, this placement certainly has merit.
We’re going to take into account Calafiore’s entire resumé to justify this placement. First, he placed second on season 16 which was won by Derrick Levasseur, who’s fourth on this list. Second, he won season 22 of the all-star season playing what’s known as a “perfect game” in which he never received a vote for eviction, and won a unanimous vote from the jury at the end. Again, this was during an all-star season!
Calafiore was known for making a terrible mistake by not evicting Levasseur in season 16, a move in which ultimately cost him the grand prize. Instead of letting it ruin his life, he learned from his mistake to win season 22 and become only the third castmate ever to make the final two twice. Watch him make the right move here at the final three:
1. Dan Gheesling (Season 10)
If not for a bitter jury on Dan’s second season (season 14), Dan would have been the first (and only) two-time Big Brother winner. Gheesling, along with with Cody Calafiore, also played a perfect game during season 10 and despite having his closest ally voted out in week 1, managed to stay under everyone’s radar by throwing early challenges to make himself not look like a main threat.
It’s pretty undeniable that Dan is the best player (and winner) in the history of Big Brother, finishing first and second, respectively, in his two seasons. Dan made for great TV, had a better grasp than anyone else in the house, and wasn’t afraid to get blood on his hands by betraying and backstabbing alliances to get himself further in the game. Dan once said in his most famous eviction speech, “Day one I entered this game and I had to get blood on my hands, and every week it’s been piling up and piling up… and now I’m up to blood on my elbows.” Dan always did what he had to do, and in turn pulled off the most sinister, conniving blindside of all time:
The complexity of this move is historic. He was somehow able to convince HOH and POV winner, Danielle Murphree, to change her nominations and put up her showmance partner, Shane Meaney, and take himself off the block. He convinced her that he would still vote for Ian, but we all know how it eventually turned out. There’s only a handful of people we can think of that could pull off a move like this, and it’s a shame that Dan wasn’t rewarded with a fair jury in his second season.
In the end, Dan Gheesling is the best player and winner to have entered the Big Brother house, and it’s going to be a long, long time before anyone usurps him of that title.