There have been 26 seasons of Big Brother and hundreds of houseguests who have traded their privacy — and possibly their sanity — for a shot at being crowned the winner. But who is the most iconic of those players? Which players changed the game, beat the system, or maybe just won America’s heart?
We’re going to break down our top eight here at PopCulture — let us know in the comments if you agree or disagree with our ranking.
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8. Ian Terry
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Starting with number eight on our list, we’ve got Ian Terry, who became the youngest winner in the show’s history in Season 14 back in 2012 before returning for All-Stars in 2020. Ian won fans over right away, as he was both a really sweet guy and basically a genius, and his six competition wins certainly bulked up his resume.
Ultimately, his ability to win in the final two against Dan Gheesling (who you know is also going to make an appearance on this list) was Ian’s biggest strength and weakness. Some people think that the jury just wanted to give the win to anyone but Dan, but others think it was Ian’s power of persuasion that won them over. It’s tough to know in the end, but it led to a pretty iconic victory and solidified Ian a spot on this list.
7. Vanessa Rousso
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Next up at number seven on our list is Vanessa Rousso, who is our only one-time player in the top eight. Despite not even winning Season 17 in 2015, Vanessa is widely regarded as one of the best strategists in Big Brother history, and watching her control the house makes Season 17 a must-see.
Watching Vanessa make deals might send you spinning, but she had her hands in basically every eviction, and she made it all the way to finale night before being cut by season winner Steve Moses. And honestly, that was because Steve knew she’d win against anyone else in a final two.
6. Tyler Crispen
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Another strategic mastermind makes his way to number six on our list with Tyler Crispen from 2018’s Season 20 and All-Stars. Maybe I’m biased because BB20 was the first season I watched, but Tyler is another phenomenal player who didn’t win his season, and I think he was robbed. Not only was Tyler the puppet master running the dominant Level Six alliance, but he was also a total fan favorite and won six competitions.
He was super well-rounded socially too, and he managed to engineer it so that he would make final two regardless of who was in the final three. Unfortunately, that all came back to bite him, because people trusted him so much they felt lied to and betrayed, and ultimately they gave Kaycee Clark the win over Tyler in the final two.
5. Britney Haynes
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At number five on our list, we have a player whose Diary Room sessions made her a legend: Britney Haynes from 2010’s Season 12 and 2012’s Season 14. Britney has always been one of the most entertaining players in Big Brother history, and while it never hurts to have America on your side, she didn’t do too badly in the game either.
Britney made it to the top four of her original season before The Brigade alliance came for her, she made it to the top eight of her second season, and she probably would’ve gone further if it wasn’t for Dan’s Funeral — but again, that’s coming up on our list.
4. Danielle Reyes
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We’re throwing it back to old-school Big Brother for number four on our list: Danielle Reyes. Danielle is one of the most iconic players from the early days of Big Brother, competing on Season 3 in 2002 and returning for All-Stars in Season 7 four years later.
Danielle is widely regarded as another player who was robbed of a win. Her strategic work definitely outweighed her competition wins, but it was her Diary Room sessions that ended up screwing her over on her original season. At the time, the jury wasn’t sequestered, and they decided to turn against her when they saw what she said.
Fans of a time thought it was unfair, and apparently so did the producers, because they changed the rules so the jury is sequestered. Sparking rule change? Iconic, just like Danielle.
3. Janelle Pierzina
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We’re down to the top three most iconic Big Brother players of all time, and you know the queen of Big Brother herself, Janelle Pierzina, had to be on here. Janelle is the only Big Brother player to appear on four different seasons (Season 6, 7, 14, and 22), and two of those seasons were All-Star seasons, so that kind of speaks for itself.
Despite having made it to finale night twice, Janelle has been cursed to come in third both times, but she’s made such an impact on the game, even as a non-winner. Competition-wise, Janelle set the record for most individual competitions won in a single season with nine competition wins in Season 7. That’s a record that would go on to be tied by Michael Bruner just a measly 17 seasons later before it was broken in BB25 by Jag Baines whose new record was tied by Makensy Manbeck in BB26.
Janelle was also the first winner of America’s Favorite House Guest, which she won with her iconic Diary Rooms, and by being the sole vote to evict her showmance, Dr. Will Kirby, in Season 7.
2. Dr. Will Kirby
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And speaking of Dr. Will, he’s coming in at number two on our list. Many have tried, and many have failed, to replicate the magic of Dr. Will’s gameplay and manipulation tactics after he won Big Brother Season 2 in 2001, but none have been able to.
It’s especially impressive because if you know, you know, Season 1 of Big Brother didn’t exactly provide a blueprint on how to play the game. And in All-Star Season 7, Dr. Will did it again, using his charm and intelligence to make it all the way to the final four, despite not winning a single competition. Only Dr. Will could turn begging to go home into a strategic move not to go. There’s only one player Big Brother fans could even argue would beat Dr. Will on this list…
1. Dan Gheesling
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…And that’s Dan Gheesling. Dan is by far the most popular Big Brother winner, having competed first on Season 10 in 2008 before returning for Season 14 in 2012, and he’s popular with good reason. He’s a strategic mastermind and the first-ever player to make it to the final two twice, winning once.
Dan managed to walk the line between this hilarious and sweet guy and a cutthroat player, making him both beloved and feared by his competitors. And while Dan always had control of what he was doing, iconic moments in Big Brother history like Dan’s Funeral and Veto Ceremony Roulette made him a total wildcard, a.k.a. super fun to watch.
Do you agree with our ranking?
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