Oh, Brother! The Most Conniving, Manipulative, Intelligent Big Brother House Guests Ever
Tyler Crispen — Big Brother 20
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The most recent contestant to appear on this list, Tyler Crispen made an immediate impact on BB 20. Utilizing his natural athleticism and outgoing personality, Tyler quickly established himself as a threat. Despite this obvious advantage, Tyler managed to avoid eviction three times. In total, Tyler notched three HoH wins and three Power of Veto wins. Tyler spearheaded the Level Six alliance and wound up reaching the final three with fellow Level Six members Angela Rummans and Kaycee Clark. Tyler finished as the runner-up to Kaycee, but took home America’s Favorite Houseguest.
Drew Daniel — Big Brother 5
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Riding a strong alliance and a showmance to the final two, Drew Daniel had a relatively easy path to victory. Drew won four Head of Household competitions and one PoV. Drew’s biggest, and most shocking, move came at the end of the game. Tasked with deciding who would join him in the final two, Drew picked Michael over Diane — his showmance. Most impressively, Drew reached the final without ever being nominated for eviction. He may have shocked Diane, but he made the right decision — ultimately taking home the $500,000 prize by a vote of 4-3.
Frank Eudy — Big Brother 14 & 18
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Frank may be one of the most well-liked contestants in Big Brother history. On BB 14, Frank grabbed attention by partnering with Mike Boogie and commencing a showmance with Ashley Iocco. Unfortunately, the rest of the house saw him as a threat and consistently nominated him for eviction. Frank won three HoH’s and three PoV’s before eventually falling in Week 8. Frank’s return to the BB house didn’t go as planned. Before being evicted in Week 5, Frank failed to win either an HoH or PoV competition. Although he hasn’t come close to a final, Frank will be remembered for being one of the best competitors in the show’s history.
Frankie Grande — Big Brother 16
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Most well-known for being Ariana Grande’s brother, Frankie had quite an impressive showing on BB 16. Frankie was a part of two alliances — Bomb Squad and The Detonators — and fared very well in competitions. Between his three PoV wins and five HoH wins, Frankie proved he could beat anyone in the house. After shielding his familial ties with Ariana for many weeks, Frankie decided to reveal the truth in an effort to help his game. Things seemed to calm down until Week 11. Frankie triggered a twist that nullified his HoH and Veto wins and was promptly evicted — finishing in 5th place.
Kaysar Ridha — Big Brother 6 & All-Stars
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Poor, poor, Kaysar. Kaysar is one of the most polarizing competitors in BB history. Some view him as a top-notch player, while others believe he is vastly overrated. On BB 6, Kaysar’s game was ultimately done in by his blind faith in his allies. After leading the Sovereign Six alliance through the early parts of the game, Kaysar was blindsided on Day 33 and evicted from the house. However, a fan vote led to Kaysar’s return only one week later. In his first HoH competition following his return, Kaysar cut a deal with Jennifer Vasquez — allowing her to win the HoH in return for safety. Kaysar was betrayed yet again, and was evicted by a unanimous vote. He later returned for BB All-Stars, but once again finished in 10th place.
Jordan Lloyd — Big Brother 11 & 13
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Since the debut of Big Brother there have been a few showmances that have blossomed into something more outside of the house. However, the most beloved couple in show history is Jordan Lloyd and Jeff Schroeder. Jordan and Jeff got together on BB 11 and nearly reached the final together. Jeff settled for 5th place, but Jordan topped him and was crowned the winner. In addition to winning two HoH’s, Jordan survived the block four times. Two seasons later, on BB 13, Jordan and Jeff returned and once again advanced far in the game. This time she fell just short of the final, finishing in 4th place.
Marcellas Reynolds — Big Brother 3 & All-Stars
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Marcellas’ claim to fame is an unfortunate one. Appearing on BB 3, Marcellas found himself in the final five. Placed on the block alongside his friend Amy, Marcellas won the PoV competition. His PoV win would allow for his game to continue — instead, Marcellas made the worst move in BB history. He didn’t use the PoV and was subsequently evicted. His time on BB All-Stars wasn’t as smooth, as Marcellas was sent packing in Week 6.
Josh Martinez — Big Brother 19
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The winner of BB 19, Josh Martinez is one of the most explosive personalities to ever walk into the Big Brother house. He would yell, he would cry, he would smack pots and pans together, but in the end, he would win. Josh’s rivalry with the group consisting of Jessica Graf, Elena Davies, Mark Jansen and Cody Nickson, will forever be remembered. In aligning himself with Paul Abrahamian and Christmas Abbott, Josh found himself in a great position. Josh won three HoH competitions — including the final one — and took Paul with him to the final two. Josh’s bold decision paid off as the jury voted 5-4 in his favor. After winning BB 19, Josh has most recently appeared on MTV’s The Challenge: War of the Worlds.
Ian Terry — Big Brother 14
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Ian may have played what most would consider a dirty game, but there is no denying he was a gifted player. Coached by Mike Boogie, Ian was a threat throughout the game. He won four HoH’s and two PoV’s. The greatness in Ian’s game was getting the house to like him while he was secretly implementing a more devious plan. Ian defeated Dan in the final by a vote of 6-1, despite many believing Dan was the more deserving winner.
Daniele Donato — Big Brother 8 & 13
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Daniele may not get the due she deserves when it comes to her game play. The big twist of BB 8 was that the players would have a rival in the house. In the case of Daniele, it was her father — Evel Dick. Daniele made it to the final two on the strength of two HoH wins and five PoV wins. Daniele was named the runner-up, losing to her father. Daniele returned for BB 13 and won two more HoH’s. She was eliminated on a Double Eviction night, giving her an 8th place finish.
Britney Haynes — Big Brother 12 & 14
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Utilizing a great social game which was buoyed by her wit and humor, Britney Haynes had two successful runs on Big Brother. On BB 12, Britney won one HoH and three PoV competitions en route to the final four. Unfortunately, Britney was blindsided and became the 6th member of the jury. America’s Favorite Houseguest returned for BB 14, and was once again blindsided. One of her alliance members, Frank, put Britney on the block and she was sent home by a 4-1 vote.
Derrick Levasseur — Big Brother 16
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Derrick was a good contestant, for sure. However, he also went against a bunch of low-end contestants who couldn’t come close to matching his prowess. Derrick powered his way through the game with an efficiency and dominance that has rarely been replicated. He won four HoH competitions, and was never put up for eviction. He won the final by a vote of 7-2 — a vote indicative of his performance throughout his stay in the house. An opportunity to play in an All-Star season would be a great barometer for Derrick.
Janelle Pierzina — Big Brother 3, All-Stars & 14
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Janelle is one of the true legends of Big Brother. Her performances on BB 3 and BB All-Stars are still discussed to this day. Her first time around, Janelle was a member of the Sovereign Six and was pitted in a fierce battle with the rival group — The Friendship. Janelle couldn’t quite get the job done and had to settle for 3rd place. On All-Stars, Janelle was a powerhouse. She won a staggering four HoH’s and five PoV’s. Janelle was able to evict Will — no small feat — but once again finished in 3rd. Despite her poor showing on BB 14, Janelle remains one of the best competitors the show has seen.
Rachel Reilly — Big Brother 12 & 13
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Rachel, in a similar manner to BB 19‘s Josh Martinez, had a way of getting under peoples skin. Her first crack at the game came on BB 12. Her personality rubbed a ton of people the wrong way, and led to a unanimous eviction in Week 5. Rachel returned for BB 13 and was a different competitor. She won the HoH four times, snagged two PoV’s, and survived the block on five occasions. Rachel reached the final and took home the grand prize by a vote of 4-3. While many fellow contestants may not have cared much for her, Rachel still has an unwavering fan base.
Danielle Reyes — Big Brother 3 & All-Stars
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Danielle is known for being one of the best strategic players in BB history, and perhaps one of the one-or-two best players to never win. Danielle traversed through BB 3 alongside her ally, Jason Guy. However, in a much-debated decision, Danielle’s game was partially blown up by the show’s decision to run her Diary Room confessionals for the Jury. Her confidence and boastful ways in the DR perhaps swayed the Jury and led to her defeat in the final two. When she returned for All-Stars, Danielle was an immediate target due to her strong reputation as a strategic genius. Despite the target on her back, Danielle nearly made it to the end for a second time. Although she finished in 6th, there is no mistaking her greatness as a player.
Mike Boogie — Big Brother 2, All-Stars & 14
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You aren’t a true Big Brother fan if you don’t know Mike Boogie. Boogie first appeared on BB 2, and alongside Dr. Will formed arguably the most formidable alliance in show history. Boogie, Will and Krista Stegall formed ‘Chilltown’, an alliance that involved a showmance and a bromance. Boogie wound up finishing the season in 8th place, but cemented himself as one of the most known contestants to date. Boogie returned for All-Stars and stepped up his game. Aligned with Will yet again, the duo advanced to the final four. Boogie would ultimately win the season by a vote of 6-1. His third season didn’t go well, but Boogie’s status as a legend had already been cemented.
Dick Donato — Big Brother 8 & 13
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Dick Donato, better know as Evel Dick, was a force both strategically and physically. First appearing on BB 8 with his estranged daughter, Daniele, Dick won three HoH’s and one PoV before reaching the final two with Daniele. Dick won the grand prize by a vote of 5-2. There was some controversy, however, due to his brash ways and proclivity to verbally attack fellow housemates. Nonetheless, Dick returned for BB 13. Dick was forced to leave the game early on, due to what he would later announce was a HIV-positive blood test.
Paul Abrahamian — Big Brother 18 & 19
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If you don’t consider Danielle Reyes the best player to not win BB, you likely consider Paul Abrahamian to be that person. Paul’s first season was BB 18. Despite being nominated for eviction six times, Paul reached the final two and won three HoH’s and three PoV’s along the way. Paul was topped by Nicole Franzel in the final by a vote of 5-4. Paul didn’t have to wait long at a chance for redemption, as he immediately returned for BB 19. The only veteran in the house, Paul managed to control the entire season. He tallied three HoH and five PoV wins, and was brought to the final two by Josh Martinez. In heartbreaking fashion, Paul was once again on the wrong end of a 5-4 vote. His 14 competition victories are the most in BB history.
Dan Gheesling — Big Brother 10 & 14
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An argument can be made that Dan Gheesling is the best BB contestant of all-time. On his initial season, BB 10, Dan had the entire house pitted against him. He was hated by mostly everyone, yet found a way to stay alive thanks in part to his own victories — three HoH, two PoV — and a secret alliance with Memphis. Dan reached the final without accruing one eviction vote, and took home the money by sweeping the Jury vote, 7-0, against Memphis. Dan returned for BB 14 and put together another scintillating performance. The magician saved his game by hosting his own ‘funeral’ at a Veto meeting, and pushed his way back into the final two. Due to what many believe was a jealous jury, Dan lost to Ian by a vote of 6-1.
Dr. Will Kirby — Big Brother 2 & All-Stars
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The Godfather of Big Brother, Dr. Will Kirby. Perhaps the shrewdest strategist the show has ever seen, Will paved the way for the likes of Dan and Paul. Despite not winning a single HoH on BB 2, ‘The Puppet Master’ reached the final two. Will was nominated for eviction four times, but kept himself alive with his mind and persuasion. Will’s second chance at glory was ended by Janelle in the final four of BB All-Stars. After weeks of controlling the house alongside Mike Boogie, Will’s reign came to a crashing halt. Will’s ability to openly manipulate his fellow competitors was a work of art. If you put together a Mt. Rushmore of BB contestants, Will would be the first person added.
