Top 5 Big Brother Players of All-Time

Updated: Sep 11

If you are like me, you are a huge Big Brother fan. When I first heard that we were finally getting another edition of Big Brother All Stars I was pumped. Unfortunately, this season has been rather underwhelming. This led me to start thinking about past seasons of Big Brother and I began making top 5 all-time Big Brother lists. Over the next few weeks, I will be releasing my top 5 lists including, top 5 to never win, top 5 most overrated winners, top 5 most underrated winners, top 5 seasons ever, and more. This week I will be starting with my top 5 WINNERS of all time. I considered doing a top 5 just in general but it is so hard to narrow down winners vs non winners so at least for now I will solely focus on people who won a season. I am only human and I have my own personal biases so to make this list a little easier to understand I will give you a little insight into what I look for in a winner.


First, I am not a huge fan of the floater strategy. There are a few times I think this strategy goes beyond floating and into a strategic manipulation and control game but overall floaters do not do it for me (sorry Andy). Second, I am a big fan of solid alliances specifically duos which are reflected in my rankings. In addition, I heavily penalized players who I thought shouldn’t have won the vote (Kaycee and Ian). This doesn’t mean that I didn’t think they were great players just that I thought the person sitting next to them deserved the win more. Lastly, I love a good comp beast but I also respect a great puppet master/deflector. If a winner is not going to be a comp beast, I expect them to be the person behind the curtain controlling the game and with the ability to survive when the target is on them. So, with that behind the curtain look into my brain let’s begin.


  1. Dan Gheesling (Winner Season 10, Runner Up Season 14)-

Anyone who has talked to me about Big Brother knows my favorite player of all time is Dan Gheesling. I could write a book on why (don’t tempt me). I believe he is the best player of all-time but for now I will keep it short and to the point. He and Memphis formed a potent duo known as “The Renegades.” He won 3 HOH’s and 2 Veto’s in season 10 to go along with 1 HOH and 1 Veto in season 14. He is the only player ever to get 1st and 2nd. In my opinion he played a better game during season 14 when he was runner-up. The Big Brother funeral was a stroke of genius. His jury answers and jury management in season 10 was also perfect as shown by his 7-0 win. In season 10 he was the target week 2 and yet flipped the script and dominated. Season 14 he started as a coach, formed the quack pack, stabbed everyone in the back time and time again and still made final 2. The top 3 for me are all close but Dan played a nearly perfect game in two seasons, so he gets the edge for the top spot.


2. Dr. Will Kirby (winner Season 2, 4th Place Season 7 All Stars)

Many people believe Dr. Will is the best of all time and there is an argument to be made. He started by winning season two (the first real season). In that season he was nominated 4 out of 10 times. Keep in mind this was before the power of veto, so he had to rely solely on his mental game to keep himself. He time and again convinced people to keep him and controlled the whole house despite losing his friends early in the game and constantly being targeted. He then returns for Big Brother All Stars and in my opinion plays an even better game. Chilltown (Dr. Will and Mike Boogie) has a target on their back from day 1 but he manages to convince the people going after him to team up with him all the while targeting them. He played a near perfect game with Erica convincing Janelle over a bottle of wine to vote him out, being his one mistake that cost him the game. This man finished 1st and 4th without winning a single HOH or Power of Veto. Not to mention his infamous, “I hate you all” speech which was just great.


3. Derrick Levasseur (Winner Big Brother 16 and supposedly puppet master of season 22)

Derrick played a flawless game in season 16. He never went on the block and never seemed in danger. The only chance he had of losing was if Cody, his fellow Hitman duo member, didn't take him to the finals. There really is not much to say he won HOH 4 times and never sniffed the block and won by a 7-2 vote. He controlled the house from the start and the only person who ever saw it outside of Cody was Nicole F. who he immediately took out after realizing she was catching on. The thing that holds him back from top 2 for me is he only did it once whereas Dan and Will both have won and made it far again during a second season.


4. Hayden Moss (Season 12 Winner)

There are so many different options for this spot. The top 3 for me is solid and there’s no convincing me otherwise. After that there are so many close winners that I had a hard time picking these next two. Hayden is a bias pick for me. The Brigades may be my favorite alliance ever and Hayden was the comp beast of this alliance winning 4 HOH’s and a veto. His best move in my opinion was taking Lane over Enzo to the final two. His mental and Social game wasn’t on the level of the top 3 but was still solid. That combined with a strong comp game and a great alliance gives him the edge for the 4th spot.


5. Jun Song (Winner Season 4)

This was the toughest one for me. Some people think Jun played the original “floater” game. I disagree. I see how well she controlled the house and had her hands in so many decisions as a strong mental and social game. She won 1 HOH and 1 Veto and was able to easily win in the final two with a 6-1 vote. There are plenty of options for 4th and 5th and I could see arguments for plenty of other players.

So where did I go wrong? What would you change and why?


While you're here, check out the podcast- Cup to Cup | The Comedy Podcast. New episodes every Tuesday!


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