The Best & Worst Big Brother Winners

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By: Emily Miller

With a new season of celebrity Big Brother about to start, super fan Andrew Barnes and I thought it was the perfect time to reflect back on the best and worst of the Big Brother champions.

So GRAB A LIFE VEST, we’re about to dive in.

21. Andy Herren (Season 15)

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I really don’t have a lot to say about Andy other than he is the worst. Like season 15 was a mess, but really, ANDY?!?! Ugh. It is going to take a lot to ever get him off the bottom of my list. EVER. –A.B.

20. Adam Jasinksi (Season 9)

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If you’re thinking, wait WHO? You’re not alone. Adam was the winner of the awkward winter season of Big Brother that was quickly thrown together because of the writers’ strike. The season featured weak players with the worst twist ever, “Till Death Do You Part” which forced contestants to pair up and form weird romantic connections. An uninspired win, during a terrible season, paired with eventual arrests for Drug Trafficking and tax evasion leave him at the bottom of our list. Still somehow better than Andy though. -E.M.

19. Marissa Jaret Winokur (Celebrity Big Brother Season 1)

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It’s a travesty that Marissa won the first season of Celebrity Big Brother. She seems like a sweetheart, she really does, but Ross Matthews was the clear winner of the season. I had to pick up my jaw off the floor when Julie announced it was Marissa. Her game was terrible and she never made any decisions for herself. Ross may have bounced back and forth but Marissa, well, she was just boring. –A.B. 

18. Maggie Ausburn (Season 6)

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Season 6 was one of the best and most exciting seasons ever, which makes Maggie’s eventual win all the worse. In a colorful season with Jame’s infamous swearing on the bible, Jedi Howie and Janelle, and Kaysar’s bittersweet exit paired with his epic return, it’s absolutely bizarre that Maggie won. Head of the worst named alliance in BB history, “The Friendship” (hilariously called The Nerd Herd by Janelle), her only achievements were being the least bold and insulting, with a lot of friends in Jury. – E.M.

17. Steve Moses (Season 17)

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Honestly all I remember about Steve was his pacing. Steve is the CBS “nerd” arch type filler of season 17 and somehow won? This is still shocking to me as his only real game play was his hatred of the twins and in the end voting out Vanessa. But here he is, a winner, so he takes spot 17. – A.B. 

16. Ian Terry (Season 14)

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Ian was a perfectly fine player. He had some competitive wins when he needed and a smart social game as the house nerd. He, in theory, could have been higher up on this list. HOWEVER, all points are lost because the real winner of that season should have been Dan Gheesling. Dan’s game play on that season was masterful and as he sat next to Ian in the final two, it should have been an obvious choice. But the Jury ended up being bitter, which resulted in Ian’s truly unearned victory. – E.M.

15. Lisa Donahue (Season 3)

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I said it then, I’ll say it now, I’ll say it in ten years: Danielle deserved to win. This season coined the phrase “bitter jury” and I firmly believe Lisa winning was the reason the Jury is now sequestered. Lisa only won because the jury saw their confessionals (and Danielle call Roddy the devil…) and hated Lisa less than they hated Danielle, even though Danielle played a way stronger game. At least she won some competitions. –A.B. 

14. Josh Martinez (Season 19)

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Josh may not be the most deserving winner, but he’s certainly one of the most interesting. With a paranoia attack setting in during week 1, he cried his little heart out and had many in the house comfort him. He then moved on to crazy town and had a breakdown on several contestants fueled by anger. Yet somehow his sporadic game play made him un-threatening to competitors and endearing to his alliance. With an ability to pull out competition wins when necessary and his absolute loyalty to Paul, he earned his spot in the final two. Paul still should have won, but when Josh cried at the news that he won, I was inexplicably happy as well. –E.M. 

13. Eddie McGee (Season 1)

Big Brother 1 Eddie, a single student from Arlington, TX

Eddie was really hard to place on this list. Of course, as the first winner of Big Brother, he deserves to be recognized, but he played a totally different game. The winner was decided by America, rather than his fellow house guests. It was a popularity contest, and for that he ends up in the middle of the pack. –A.B.

12. Jordan Lloyd (Season 11)

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Jordan is also a hard one to place on this list of winners. She’s a sweetheart and she was a great player when she came back for season 13, but she didn’t win season 13 (BUT SHE COULD HAVE). She won season 11, where she was very lucky to even make it to finale, being protected by Jeff (although it was a great alliance) and not being seen as a physical threat. But, she won at the end when it mattered and secured herself a spot smack in the middle of this list. – A.B. 

11. Kaycee Clark (Season 20)

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Within the first week Kaycee joined the Level Six alliance with five of her other house mates, and then let that be the extent of her game play for the first half of the season. She turned into a competitor in the second half of the game when she needed to, winning two HOH’s and five of the last six PoV’s, an impressive feat. However, when she made it to the final three, she sat there with two other alliance members and incredible players, Tyler & Angela. Any one of those three could have won and it would have been deserved. So overall, a good game, I just wish she distinguished herself from the pack more. –E.M. 

10. Nicole Franzel (Season 18)

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When she first competed in BB 16, she came out with an aggressive game play and targeted the big alliance in the house, which eventually lead to her eviction. When she came back for Season 18, she had an even bigger target on her back as a returning vet. Yet she learned her lesson well and played a low key game making solid alliances, small competition wins scattered throughout the season and an excellent social game. (She had a showmance with Corey, and is now currently engaged to Victor.) When she beat Paul in the final vote, it became the first time in Big Brother history that a woman beat a man. –E.M. 

9. Drew Daniel (Season 5)

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A lot happened season 5 (the twin twist blew my mind). Drew played a really low key game that almost kept him out of the top 10. What kept him in: saving his showmance, Danielle, from the block knowing it would send his fellow horseman Jase up and home, and then sending Danielle, home right before the end. He knew he couldn’t beat either one of them. Was it cold? Sure. Did it win him the game and a spot in our top 10? Absolutely. – A.B.

8. “Evel” Dick Donato (Season 8)

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Self proclaimed “Evel” Dick walked into the BB house at a serious disadvantage. He was the oldest contestant, looked different from everyone else, and had the season’s big twist directly affect him; he was now trapped in the house with his estranged daughter Danielle. But both he and his daughter conceded that blood was thicker than water, and set their eyes on the money. A decent competitor and one of the game’s best strategists, he and Danielle didn’t let anyone stand in their way. The father daughter duo made it to the final two, an impressive feat on it’s own. Even more impressive? After treating the house terribly for months (remember when he poured iced tea on Jenn’s head?) he convinced them all to vote for him. He would have been higher on the list, but his eventual win belonged to Danielle as much as it did him. –E.M.

7. Hayden Moss (Season 12)

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Hayden put a target on his back on Day 1 by taking the first HOH competition. But he parlayed his power into one of the best alliances the game as ever seen, “The Brigade.” He ended up winning four HOH competitions and yet somehow convinced the house that him and his giant muscles weren’t a physical threat. He made it to the final three with two of his alliance members from Day 1. Overall Hayden was just a strong, clean competitor and a really solid winner. – E.M. 

6. Derrick Levasseur (Season 16)

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Derrick played the perfect game. He was loyal, manipulative, smart, didn’t make enemies and was never even nominated. All this would suggest he should take the number one spot. But his game was /too/ perfect. He was the clear winner from the jump, he didn’t have to work for it. He never had to fight to stay in the game, and so here he is at number six. –A.B.

5. Rachel Reilly (Season 13)

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Definitely the most divisive winner. Like her or not she played a very good game when she was in the house (both times). She was the clear winner of season 13 after she masterfully moved through the game with her veterans alliance and outsmarting Danielle’s masterful attempt to break them up. Not to mention everyone already knew her strategy going in and she wasn’t the first to go. She plays the game with unwavering confidence, making her one of my favorite contestants of all time and earning her a place in the top of this list. – A.B.

4. Mike “Boogie” Malin (Season 7, Big Brother All Stars)

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Season 7 was the season of All Stars. The house was filled with the best and most popular losers from the previous six seasons, with one notable exception. (Season 2 winner, Dr. Will Kirby) The season was truly an all star season with all of America’s favorites competing in epic competitions to earn the title of Best of the Best, and Boogie outsmarted them all. His win was absolutely incredible. He made top notch alliances with Dr. Will and Janelle, and had a showmance with Erika. And though he didn’t win many competitions, he had one of the best social games ever, and managed to convince everyone he wasn’t a threat until it was too late. When he made it to the final two with Erika, the house knew the obvious decision they had in front of them. His win was an impressive feat on it’s own, but knowing he beat the BB all stars, gives him one of the top spots. –E.M.

3. Jun Song (Season 4)

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Jun played a great game. Creating an early alliance with her ex-boyfriend was a crucial first step. Jun won when was necessary, played one of the strongest social games, I would argue, ever, relying on her relationships to make it all the way to the final two and getting very little blood on her hands. Jun perfected the floater strategy (and while frowned upon now) proved that you didn’t have to have a huge challenge win resume to win the game. Not to mention she accomplished all of this while never having a vote cast against her until she beat Alison 6-1 for the title.

2. Dan Gheesling (Season 10)

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After week 1, Dan seemed to be a sitting duck. His best friend had been evicted from the house, and Dan was the sole vote to keep him. Yet he used that to convince people that he was loyal and harmless. He also threw competitions for the first few weeks to solidify his weak persona.  And then once he had everyone’s trust and friendship, he used it to manipulate and control the entire house. He had a hand in every eviction, while maintaining a flawless social game. And when he decided to actually compete, he ended up winning 2 POVs and 3 HOHs.  He made it to the finale with his alliance member Memphis, and then became the first Big Brother contestant to win unanimously. –E.M. 

1. Dr. Will Kirby (Season 2)

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Do not get me wrong, the Evil Doctor was mean. He was sly and he was manipulative, but it worked. He made it to the end, and he won by a 5-2 vote. He set the pace and level of the season, created the first “alliance” and wrote the book on aggressive/shady game play and made it to the end with no hoh wins, and his fellow housemates gave him the money ANYWAY. That, to me, is a champion, so Will nabs the top spot on this list, and it was well earned. And, hey, at least he wasn’t the one who scrubbed the toilet with Hardy’s toothbrush. –A.B.

As always, sound off in the comments section below.

One comment

  1. You don’t know much about Big Brother lol. Was this ranking based on how good of a player each winner is? Or just who you personally like? Because both Andy and Maggie are two of the best players to ever win.

    Like

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