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10 Best Contestants on ‘Celebrity Big Brother,’ Ranked

Celebrity Big Brother has been a mainstay spin-off of the British series and has aired many seasons since it began as a spin-off of the traditional reality competition series. In the U.S., there have only been three celebrity seasons to date, but they have been all well received. Each one, like the main show, features an eclectic mix of houseguests. These range from athletes to actors, musicians to hosts and TV personalities, reality show stars from other franchises, and others.

The best players on Celebrity Big Brother aren’t necessarily the ones who won their respective seasons. They brought something unique to the table, whether it was for their heartwarming friendships, villainous status, or competition prowess.

Big Brother 2000 TV Show Poster

Big Brother

Release Date
July 5, 2000

John de Mol, Ron Diesel

Julie Chen Moonves , Clayton Halsey , Nicole Franzel , George Boswell , Daniele Donato , Janelle Pierzina


10 Kato Kaelin (Season 2)

Placed: Eighth

Kate Kaelin on Celebrity Big Brother looking shocked, hands on his head with tattoo sleeves on his arms.
Image via CBS

Kato Kaelin is an actor and radio and TV personality, but he rose to fame as a key witness in the infamous O.J. Simpson murder trial of the ‘90s. He was a mystery when he appeared in the cast, seemingly the one who might be ostracized from the others for his former friendship with the late football star and accused murderer. But what fans loved about him was his positive attitude and the unlikely friendship that grew between he and actor Tom Green.

As two of the older players, the guys didn’t quite jive with the younger stars. But they forged their own path, and simply enjoyed their time in the house together. What’s more, he even won a few competitions, solidifying his position as more than just a floater but someone who truly came to play.

9 Tom Green (Season 2)

Placed: Sixth

Tom Green making an unimpressed face in the Diary Room on Celebrity Big Brother.
Image via CBS

A quirky and eccentric comedian, host, actor, filmmaker, podcaster, and even rapper, Tom Green is known by anyone who grew up in the ‘90s and early ‘00s for his starring role in movies like the cult film Freddy Got Fingered and Road Trip as well as his talk show The Tom Green Show. Unapologetically his goofy self, fans were surprised to see a more subdued version of Green on the show, despite the fact that the show put him in an uncomfortable situation, as it did everyone else who had to let their guards down and compete in sometimes humiliating competitions.

Along with his surprising friendship with Kato Kaelin, Green was the subject of Internet searches through his time on the show as fans wanted to know the meaning behind the various custom T-shirts he was wearing. It turns out they were to support a friend with cancer, a disease Green himself has beat. His honesty, genuine personality, and friendly attitude was not what viewers were expecting, but it was a pleasant surprise that made him a fan favorite on his season.

8 Shannon Elizabeth (Season 1)

Placed: Ninth

Shannon Elizabeth smiling in the diary room on Celebrity Big Brother, sunglasses on her head wearing a tank top.
Image via CBS

Best known for her acting roles in movies like American Pie, Scary Movie, and Jay and Silent Bob Strike Back as well as her professional poker playing career, Shannon Elizabeth always played the stereotypical “dumb beauty.” But she proved she was anything but in real life in her shining moment on Celebrity Big Brother. During a competition where players needed to dig for letter cards through gooey substances and try to spell the longest word in the shortest amount of time, she shocked everyone. She uncovered her board to show the word “responsibilities,” which to this day, holds the record for the longest word every spelled in the game.

Elizabeth was a competition beast, winning both Head of Household and Power of Veto in the first week. She controlled a large part of the game in the beginning, but her powerful gameplay was her demise when her alliance decided to vote her out because of it. She was one of the few celebrities who put her all into the game, competing hard in every competition she was in.

7 Jonathan Bennett (Season 2)

Placed: Eleventh

Jonathan Bennett looking down, upset with his eyes wide in a scene from Celebrity Big Brother.
Image via CBS

An actor and TV host, Jonathan Bennett is often equated with his role as the object of Lindsay Lohan’s affection in Mean Girls, Aaron Samuels. Most recently, he has pivoted to hosting, working on shows like Halloween Wars and Cake Wars. He also starred in Hallmark Channel’s first LGBTQ Christmas movie The Holiday Sitter. In the game, Bennett was a strategist and strong competitor. He forged alliances, performed well in the few competitions he was in, but was immediately pegged as a power player.

Bennett’s game was short-lived because of this, but that doesn’t mean he was a bad player. He played too hard and was likeable, a deadly combination for anyone in the game. That led to his premature eviction as the first celebrity evicted from the house. But Bennett remains one of the most strategic Celebrity Big Brother players that fans wished could have stayed longer. He likely would have shaked things up in the house.

6 Cynthia Bailey (Season 3)

Placed: Third

Cynthia Bailey on Celebrity Big Brother smiling.
Image via CBS

Model, reality TV personality, and actor, Cynthia Bailey’s most notable role is as a cast member on The Real Housewives of Atlanta. She was quick to form bonds with others in the house and was part of the first alliance of the season. Bailey was saved time and time again by winning twists and while others drew targets on their back, even when her alliance was growing smaller. She was able to pivot and keep herself in the house for as long as she could.

While she made some bad decisions, influenced by lies Todrick Hall told, Cynthia came back swinging when she realized the mistake. Had Bailey been able to perform better in competitions, she could have won the whole thing.

5 Todrick Hall (Season 3)

Placed: Runner-Up

Todrick Hall on Celebrity Big Brother smiling, wearing a yellow beanie hat.
Image via CBS

Remembered as a contestant on season nine of American Idol, Todrick Hall went on to find fame elsewhere even though he didn’t win that competition. He made a series of viral YouTube videos and the rest is history. Hall was one of the most controversial players in any U.S. version of Celebrity Big Brother, garnering some backlash from viewers for the cut-throat way he played and some of the offensive things he said. But there’s no denying that from a purely game perspective, he played with a rock-solid strategy.

He aligned himself with the strongest competitive player, Miesha Tate, and worked behind the scenes to influence her decisions throughout. His tactics involved lying and deceiving when it was necessary to further his game, turning allies against one another. His speeches to the jury in the end, however, sealed his fate and he became runner-up. But when it comes to the name of the game, many may have not liked his approach from a personal perspective, but on a game level, he got himself to the end.

4 Miesha Tate (Season 3)

Placed: Winner

A close-up of Miesha Tate smiling on Celebrity Big Brother.
Image via CBS

Being such a fierce competition in her real life as a professional mixed martial artist, it’s no surprise that Miesha Tate dominated the season when it came to competitions. But she was a strategic player as well, even though her closest ally Todrick Hall was constantly in her ear. She never let anyone make decisions for her, and in the end, her loyalty to Hall proved the right decision because she beat him in the end.

While Tate has Hall’s lies and deception to thank for saving them when Carson Kressly won a Head of Household competition that would have likely put both of them on the block, Tate was no slouch. She deserved the win and worked hard for it every day she was in the house.

3 Carson Kressley (Season 3)

Placed: Sixth

 Carson Kressley on Celebrity Big Brother looking at someone on the side, pursing his lips.
Image via CBS

Filled with personality like many of the most popular Big Brother legends, Carson Kressley is a TV personality, actor, and designer who rose to fame on the series Queer Eye for the Straight Guy. He has also worked as a judge on RuPaul’s Drag Race. His Diary Sessions were among the most entertaining on the season, with fans excited every time he came on screen, anxious to hear what he might say and his clever and witty banter and jokes with others.

Any time Kressley won anything in the house, he seemed genuinely surprised and proud of himself, not thinking he could pull it off. It’s no surprise that he was deemed a threat early on since he had such a strong social game and went into the house already knowing several of the other cast members. But he was able to save himself time and time again, even though he was constantly nominated for eviction. It’s no surprise he was awarded America’s Favorite Houseguest at the end of the season.

2 Tamar Braxton (Season 2)

Placed: Winner

Tamar Braxton relaxing on the bed in Celebrity Big Brother, looking unimpressed and wearing oversized hoop earrings with a scarf on her head.
Image via CBS

Singer and TV personality Tamar Braxton starred in the reality TV show Braxton Family Values and was co-host of the daytime talk show The Real. Her time on Celebrity Big Brother was emotional as she went through many highs and lows. She opened up about her personal life in Diary Room sessions, which made viewers feel sympathetic and root for her to win, which she ultimately did.

Her game was rocky from the start since her enemy Kandi Burruss was in the house as well and she needed to navigate that sensitive and fractured relationship. Her win was historic, making her only the second winner ever on the celebrity edition of the show to win by unanimous vote and the first Black winner ever of the series, including regular season episodes.

1 Ross Mathews (Season 1)

Placed: Runner-Up

Ross Mathews sitting and leaning forward while talking in a scene from Celebrity Big Brother.
Image via CBS

His joyous personality and infectious smile made Ross Mathews an instant favorite, along with his deep knowledge of the game. Prior to joining the cast to actually play, Mathews had hosted the official web show for the regular series, interviewing evicted houseguests for many of the most popular seasons. He got his start as an intern and correspondent on The Tonight Show with Jay Leno, appeared as a weekly panelist on Chelsea Lately and as a judge on RuPaul’s Drag Race. He currently assists on The Drew Barrymore Show.

Mathews was one of few people who went into the game knowing exactly what it was all about. His knowledge of the game and its past seasons and strategies employed meant he knew how to navigate situations. In the end, however, his aggressive and deceitful gameplay and refusal to own up to the moves he made resulted in his closest ally Marissa Jaret Winokur winning over him. Many, however, believe he was the victim of a sour jury and that he actually deserved to win.

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NEXT: The 10 Celebrities We’d Love to See in ‘Dancing With the Stars’ Season 33

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