Season 23 of CBS' long-running hit reality TV show competition Big Brother is set to premiere on Wednesday, July 7, 2021. Hosted by Julie Chen, the show gathers a collection of strangers who are forced to live together in a lavish abode for several weeks, where they are challenged to make friends, forge allegiances, and avoid a vote-based elimination by whatever means necessary.
With various challenges, showmances, secret infighting, and manipulative backstabbing, the contestants face numerous hurdles while enduring their stay in the Big Brother household. To win the game, a player must overcome the odds and demonstrate at least one iconic moment of triumph on the show.
10 Eddie McGee - Season 1
In addition to being the very first BB winner, Eddie Mcgee also bore the distinction of being the youngest winner at age 21, a record that held until 2014 when Ian Terry broke it. He was also the only amputee to participate in the show, much less be crowned as champion.
While Eddie had several standout moments on the show, few eclipse the time won a sumo wrestling challenge by defeating the Houseguests and earning a luxurious massage as a reward. While that was his most iconic scene, his biggest feat includes avoiding more than three eliminations in a row and still winning the game.
9 Will Kirby - Season 2
Will Kirby is one of the most infamous contestants in BB history. The duplicitous doctor earned a rep for his manipulative gameplay, which helped him endure 82 days in the house en route to victory in Season 2.
While he coined the term "Showmance" and saved the pot-belly pig Ophelia from drowning in the house swimming pool, Will's most iconic moment that led to his victory includes the rare time he won the "Great Escape Challenge" on Day 56. Along with Bunky, Will completed the challenge first and was awarded a scenic helicopter tour of Los Angeles. That being said, Will's most iconic moment in show history includes his epic "Veto" rant in his return in BB7.
8 Lisa Donahue - Season 3
Lisa Donahue bested Danielle Reyes for first place after both spent 82 days in the house during BB3. Lisa made history by becoming the first female winner, as well as the first HoH to also win the entire game.
However, her most iconic scene came when given the chance to save her love interest, Eric Ouellette, with whom she shared a showmance for several weeks. In one of the most ruthless and strategic moves imaginable, Lisa voted against Eric's return to the show. The dramatic decision ultimately led to her making the final three before emerging victoriously.
7 Jun Song - Season 4
While her feats include forming an alliance with Allison and avoiding a single eviction vote, Jun's most iconic scene came when she won the HoH competition and was awarded a trip to attend the 20th annual MTV Video Music Awards by herself. Upon her return, she immediately nominated Jee.
6 Drew Daniel - Season 5
BB5 winner Drew Daniel amassed several historical feats during his time on the show. As the first houseguest to win four HoH competitions and compete in every single Power of Veto competition, Daniel aligned with The Four Horsemen as his key strategy.
Therefore, Daniel's most iconic scene came when he shockingly ditched his showmance, Diane Henry, and opted to take his friend and fellow Four Horsemen member Michael Ellis to the Final Two. The strategy paid off, but he lost a significant other in the process.
5 Maggie Ausburn - Season 6
Maggie Ausburn won BB6 after enduring 80 days in the house, earning four precarious eviction votes in the process. Thanks to her ties to The Friendship Alliance, Maggie was able to lead the alliance after her secret ally Eric Littmann was eliminated.
Maggie's most iconic moment came during her one time winning the "Power Roller" HoH competition during week 4, where she successfully bowled a ball the closest to a hole without entering it. Her victory immediately led to the formation of The Friendship Alliance with April, Beau, Ivette, and Jennifer.
4 Mike "Boogie" Malin - Season 7
In addition to winning BB7, Mike "Boogie" Malin has also competed on BB2 and BB14 All-Stars edition. As one of the most popular and longest-tenured houseguests, he has no shortage of iconic moments. Creating the first BB alliance in Chilltown with Will Kirby and proposing to Krista in Season 2 are among them.
However, Mike's most iconic scene from his winning season came when he shockingly nominated his long-term showmance, Erika, for eviction after winning the "Big Brother Bowl" HoH competition. Despite pretending to be in love with her early on, Mike claimed to have no feelings for Erika whatsoever in the end.
3 Dick Donato - Season 8
Despite his personal attacks on various housemates, "Evel Dick" Donato won BB8 after spending 81 days in the house. As the elder statesman in the cast, he used his wily experience to manipulate his way to the winner's circle.
While competing with his daughter Danielle and winning three HoH competitions rank among his high points in BB8, Dick's most memorable scene came when Jen stole his cigarettes, bleached them, and hid them around the house. Dick retaliated by launching Jen's wardrobe against the wall, which led to a massive fight. Walking away from the competition in Season 9 is a close second.
2 Adam Jasinski - Season 9
While he defeated Ryan Quicksall in a decisive 6:1 jury vote in BB9, Adam Jasinski's biggest moments on the show became famous for all the wrong reasons. He became a controversial figure after making disparaging remarks about disabled children during the very first competition.
Yet despite the controversy, Adam became a member of Team Christ and forged a showmance with Sheila Kennedy. His most positive moment came when won his second HoH competition in three weeks and winning his one and only Power of Veto challenge one week later.
1 Dan Gheesling - Season 10
Like Will Kirby and Mike Malin, Dan Gheesling is one of the most iconic and most experienced contestants in BB history. While Dan demonstrated superior strategy en route to winning BB10, his biggest moment came during his All-Stars return in BB14.
In one of the all-time most notorious moments on the show, Dan arranged his own funeral and recited his own eulogy during BB14. The strategy paid off when he was taken off the Veto block when he was a primary target. The move is widely hailed as one of the smartest strategies in show history.
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