Big Brother has been going strong for more than two decades, with not only regular seasons but also All-Star seasons, celebrity seasons, and a Christmas special called Reindeer Games in 2023. Through the seasons, there has been a long list of both new and returning cast members, each vying to win the big prize. Initially $500,000, the prize was increased for the last few seasons to $750,000, making the Big Brother prize one of the richest in Reality TV history.
Not all the Big Brother legends have actually won the game, be it thanks to house politics or alliances. Some are considered legends for other reasons. For some, it was how they played the game, and, for others, their insightful (and entertaining) diary room confessions. But, regardless of whether a great player won or not, anyone who follows the reality competition series will agree that the following 10 contestants are true legends in the game.
10
Rachel Reilly
Season 12 (9th Place), 13 (Winner)
Playing in back-to-back seasons, Rachel took home the win the second time she played. But it wasn’t her win that made her a legend. It was her performance on many levels. Despite having heated arguments with many other players in the game on both seasons, Rachel managed to win competitions when she needed to further herself in the game and take out her enemies. She also popularized the term “floaters” to describe players who quietly sit in the background and make their way to the end by staying out of all the house drama. The term continues to be used in the game to this day, always credited to her.
Both she and her now husband, Brendan Villegas, became a powerful duo in the game that developed a large fan following. Appearing several times in later seasons, like as a punishment in season 14 and to greet her sister Elissa Slater on season 15, Rachel has become one of the most memorable cast members in the show’s history.
9
Danielle Reyes
Season 3 (2nd Place), 7 (6th Place), Reindeer Games (7th)
Widely considered to be one of the best players in the game to never win, Danielle’s second-place finish in season 3 is what prompted the show to change its format. After a bitter jury went home and watched Danielle’s candid and hurtful diary room sessions, they chose to vote for Lisa to win instead, even though Danielle had clearly played the better game. Since then, the jury is sequestered until the final episode, not able to watch the season until after they vote.
Danielle’s strategic game play is what makes her a legend. She did not do well in competitions, but she aligned herself with people who did, including one person in the house no one would ever suspect she was working with. When she returned in the All-Star season 7, she was immediately targeted because of her reputation as a fantastic player. What’s more, Danielle blazed a trail for other Black players. As the first Black female winner of a regular season, Taylor Hale, who won season 24, revealed on Reindeer Games Christmas special that Danielle is the reason she decided to do the show.
8
Vanessa Rousso
Season 17 (3rd Place)
Another houseguest considered to be robbed of the win and named one of the show’s most strategic players, Vanessa Rousso used her skills as a professional poker player to hide her true cards. She was running the house from the beginning, central to every voting decision that was made. Everyone trusted her and came to her, even when she wasn’t the one in power, and she manipulated situations to her benefit. She always made sure others did the dirty work, so there was never blood on her own hands.
Steve Moses, the winner of her season, happened to win the final competition and made the correct decision to take Liz with him to the final two instead of Vanessa. As was revealed by the jury after the vote, most jurors admitted they would have voted for her to win had she been in the final two.
7
Will Kirby
Season 2 (Winner), 7 (4th Place)
Dr. Will Kirby, known as “Dr. Will,” is such a legend in the game and one of the best Big Brother winners. He remains part of the show to this day, handling the jury deliberation meetings every season. He even returned to be part of a competition in a recent season. His cut-throat game play rubbed people the wrong way, yet he still managed to stay in the house, despite the way he treated others. His diary room sessions with fellow housemate Mike “Boogie” Malin have become legendary in and of themselves as the pair laughed hysterically at the things they were pulling off in the house and how well they had duped people. One of the most epic speeches in the show’s history was his Veto speech where Dr. Will told everyone he hated them all, yet still wasn’t sent home.
Despite being nominated four times, and never winning a competition, Will always managed to get himself out of harm’s way. In a competition that relies so heavily on winning games, this is a feat unto itself. Responsible for the term “showmance” that continues to be at the core of Big Brother, Dr. Will even reportedly inspired Survivor legend Rob Cesterino, who said he based his game play on Dr. Will’s.
6
Ian Terry
Season 14 (Winner), 22 (11th)
The personification of an underdog, Ian Terry entered the game seeming like he wasn’t a threat. But he beat one of the show’s best players ever in a final two, ironically, after Dan Gheesling, who had returned in this season first as a coach, then as a player, mentored him. A long-time fan of the show, Ian knew how to work the game. He made alliances, sought out targets, and surprised even himself when he won multiple competitions.
Despite being dismissed as someone who was expendable, Ian proved everyone wrong. He is arguably the most inspirational player as well, revealing his autism-spectrum disorder diagnosis prior to returning for season 22. Additionally, Ian remains the youngest player to ever win the game: he was just 21 when he took home the big prize.
5
Britney Haynes
Season 12 (4th), Season 14 (8th), Reindeer Games (5th)
Britney isn’t a legend in Big Brother for her strategic game play or even competition wins. She has simply been one of the most likable, witty personalities on the show. Her diary room sessions were the most memorable part of her time on the season, so much so that fans have put together compilation videos of her best moments on YouTube. Her sarcastic tone, snarky commentary, and quick wit made her instantly enjoyable to watch whenever she went into the diary room to reveal her true feelings about fellow houseguests and what was going on in the house. It’s no surprise that in season 12, Britney was named America’s Favorite Houseguest.
Fans also sympathize with Britney, who was the only woman in a four-person alliance. Her buddies revealed to her right before voting her out that they had a three-person alliance known as The Brigade, and she had unknowingly been helping them get through the game. Being a peripheral part of one of the most successful alliances in the show’s history has also made her a legend.
4
Janelle Pierzina
Season 6 (3rd Place), Season 7 (3rd Place), Season 14 (12th Place), Season 22 (14th Place)
One of the players to have appeared the most times, Janelle garnered the reputation of being a competition beast. She set the record for the most individual competition wins ever in a single season with nine total, which was broken by Paul Abrahamian in season 18 and recently tied by Michael Bruner in season 24 and Jag Bains in season 25. She continues to hold the record for the most individual competition wins over multiple seasons at a total of 15.
Janelle has racked up numerous stats through her career on the show, including being the first female to win two Power of Veto competitions in the same season, the first recipient of the Fan Favorite Award (now called America’s Favorite Player), and the first to play 200 days in the Big Brother house. Her name and cut-throat blonde bombshell reputation has become synonymous with the series.
3
Dick Donato
Season 8 (Winner), Season 13 (Walked)
With such a big personality, it’s difficult for Dick Donato, the oldest player ever to win the game, not to stand out. He caused chaos during his season, playing the game with reckless abandon. He didn’t care who knew he didn’t like him and had no interest in keeping secrets about his intentions. He often got into heated arguments with people in the house and was known for personal attacks and intimidation. He was so confident in his game play that he used the Power of Veto on another player when he was on the block and still didn’t go home, making him one of only three players ever to accomplish this. He also won the most Head of Household competitions of his season.
Dick’s hard work led to him making it to finale night not only on his own, but also with his estranged daughter Daniele, who he vowed to protect through the game. Known as the most notorious villain in Big Brother history, referred to as “Evel Dick,” Dick’s return was short-lived. He was forced to leave the game due to an emergency. Nonetheless, he’s one of the most talked about former houseguests from the show.
2
Derrick Levasseur
Season 16 (Winner)
Often cited by new players as the person they try to emulate, Derrick Levasseur’s performance in his season is a masterclass in how to play the game. He had the perfect combination of great social game and control of every move. He was well liked and never deemed a threat, so much so that he got through the entire season without ever being nominated for eviction. Beyond that, he forged such a tight bond with Cody Calafiore that his partner in crime opted to take him to the final-two out of pure loyalty, even though he might have known deep down he was securing Derrick a win in doing so.
Derrick solidified the votes with his incredible speech to the jury revealing his real occupation: he was a police officer who had previously worked undercover. When he followed this up by listing all the moves he orchestrated in the game that no one realized, it led to one of the most shocked juries every in the history of the show. While Derrick never played again, he has returned on multiple occasions to present competitions or discuss the game. The disappointment fans revealed online when Derrick dropped out of season 22 because his daughters didn’t want him to leave is further evidence of his legendary status.
1
Dan Gheesling
Season 10 (Winner), Season 14 (2nd Place)
Widely considered to be the best to ever play the game and the first name that comes to mind when thinking of Big Brother legends, Dan Gheesling pulled out some incredible moves during his time on season 10, which many fans consider to be the show’s best season. But his most notable is Dan’s Funeral from season 14, a plan he concocted after spending 24 hours in solitary confinement as a punishment. He gathered the house together to say his goodbyes knowing he would be voted out. But his carefully orchestrated, heartfelt and anger-fueled speech completely fooled everyone, including his closest ally. He threw her under the bus to save himself, and it actually worked.
Known for quietly manipulating others, winning competitions only when it served him, and never coming across as a threat, Dan is a Big Brother fan favorite player as well. In both seasons, he aligned himself with a player he felt he could trust and could help him get to the end, and he pulled it off flawlessly.