Big Brother’s Biggest Legends

Big Brother redefined reality TV with a huge cultural impact—counting 20 seasons and production in over 63 countries and regions. What makes this show great are the contestants with their alliances, personal drama, and scheming. These 15 players kept the public glued to their couches and now deserve the spotlight.

Dr Will Kirby (Season 2 & All-Stars)

Without winning a single Head of Household competition, Dr Will Kirby relied solely on his social skills and wit to manipulate the game. His ability to convince others to do his bidding made him a puppet master. Will’s legacy as a master strategist set the standard for future players.

Dan Gheesling (Season 10 & 14)

The flawless Big Brother 10 win is often hailed as one of the best performances in reality TV history. Dan Gheesling knew how to play both a loyal ally and a ruthless backstabber. His “funeral” strategy in All-Stars remains one of the most iconic moves in the game.

Janelle Pierzina (Season 6, 7, & 14)

Proof that not only men could lead the game, but Janelle Pierzina was also a competition beast who won more competitions than almost anyone in her seasons! What made Janelle a fan favorite was her ability to fight her way out of impossible situations by being a fierce strategist.

Derrick Levasseur (Season 16)

This player’s game in Big Brother 16 was almost perfect. As a former undercover cop, he used his skills to manipulate the other contestants. Derrick controlled almost every move in the house while staying under the radar. His social game was impeccable, and he never even faced eviction—just another proof that he was in control.

Rachel Reilly (Season 12 & 13)

Rachel Reilly went from being one of the most polarizing houseguests to a beloved Big Brother legend. Known for her emotional outbursts and competition wins, Rachel fought tooth and nail for her victory in Season 13. Her persistence and refusal to give up earned her respect and a well-deserved spot among the best.

Vanessa Rousso (Season 17)

When an exceptional poker player joins the house, you can expect they will use their analytical skills to get ahead. That’s what Vanessa Rousso did in Big Brother 17. Using strategic thinking and emotional manipulation, she remained in control of the house for most of the season.

Evel Dick Donato (Seasons 8 & 13)

Evel Dick’s confrontational style in Big Brother 8 was unlike anything viewers had seen before. His constant confrontations with houseguests made him a polarizing figure—he was both hated and loved throughout the season! His willingness to do whatever it took, with determination and strategic gameplay, secured him the win in the end.

Ian Terry (Season 14 & All-Stars)

One of the youngest winners ever at 21 years old, Ian Terry was often overlooked by the other contestants but outsmarted some of the best players to win Big Brother 14. He combined logic with an incredible physical game to win key competitions when it mattered most.

Tyler Crispen (Season 20 & All-Stars 2)

Since day one of Big Brother 20, Tyler Crispen made sure to show his leadership skills. His ability to form alliances and manipulate players without them realizing it was impressive. Despite coming up just short of the win, Tyler left a lasting impression with his smarts and game strategies.

Hayden Moss (Season 12)

Staying under the radar during Big Brother 12 got Hayden Moss to the final. His charm, strategic thinking, and physical abilities helped him win when it counted most. Hayden’s victory also paved the way for his success on Survivor, proving his skills transcended one show.