Big Brother is reality television at its finest. The show takes a dozen people, mostly young and attractive, from across the U.S. and throws them into a massive house with nothing to do but scheme and backstab one another.
The show really is a crazy social experiment. What happens when people from all walks of life are confined to this house, with no communication with the outside world, no electronic devices, no books (Bible excepted), and no music? They have nothing to do but plot against one another, forge alliances, endure horrible punishments (slop or the unitard, anyone?), and compete in grueling physical and mental challenges, of course! Let’s not forget that viewers can watch their every move and hear their every word, 24/7, via live feeds. But the last man (or woman) standing takes home half a million bucks. Nonetheless, it’s understandable that players sometimes go bonkers in the house.
To date, there have been 20 winners who have stuck it out for the long-haul (not including the all-stars and celebrity seasons). A few stand out. And here, in no particular order, are 5 individuals who absolutely deserved to win, and 5 who should not have won at all.
10 Most Deserving: Will Kirby
Winner of the second season, Will (actually, Dr. Will) remains an integral member of the Big Brother family, interviewing jury members in the final episode of each season. He employed clever strategies that were unique at the time but have now been emulated by lots of players, including the secretly-named alliance (his was Chilltown) and the revealing and arrogant diary sessions chronicling one’s trickery.
In a way, he’s a Big Brother trailblazer, scheming before there was such a thing as backdoor evictions and throwing competitions. Will won despite being nominated for eviction four times, thanks, in large part, to his close friendship with Mike “Boogie” Malin and their work together to lie, cheat, and backstab their way to the final two.
9 Most Deserving: Mike “Boogie” Malin
Known for his partnership with Will Kirby in the second season, and for his interesting fashion sense that often included backward baseball caps, visors, and statement T-shirts, Mike returned to win the seventh season of the series.
Playing alongside Will once more, they revived the Chilltown alliance (you’d think players would have caught on by now!) and he orchestrated a showmance that he later said was just a lie to help him get further in the game. Considered one of the show’s biggest villains, Mike still managed to pull out a win despite being a jerk to so many because he was also oddly likable.
8 Most Deserving: Dick Donato
He smoked, he drank, he didn’t give a damn about anyone or anything in the house – except his estranged daughter Danielle. Another notorious villain – he was given the nickname Evel Dick, after all – he ruffled a lot of feathers and made a lot of noise. That made it all the more impressive when he won season 8.
Interestingly, he made it to the final two with his daughter, who he did everything in his power to keep in the house and tried to mend fences with in the process.
7 Most Deserving: Dan Gheesling
A legend in the game, there should be books written about Dan’s amazing gameplay and his ability to manipulate people and flip scripts when it seems like he’s doomed to go home. He would forge alliances with the right people, and he was always in control of the game while the other players were none the wiser. He even convinced someone to throw a competition for him, betrayed them, and still remained in people’s good graces!
Because of this, Dan took home a win in season 10. Notably, when Dan returned for season 14, he held his own mock funeral before eviction to try and get sympathy votes, and it worked! He didn’t end up winning that season, losing out to one of his biggest fans. But a single vote has never been cast against him, and he’s made the final two twice.
6 Most Deserving: Derrick Levasseur
The smartest and savviest player to date, Derrick remained in the background, yet he was actually cleverly pulling all the strings. This is a claim a lot of floaters make, but this was one that Derrick could actually back up. Quietly and effortlessly influencing every decision, he hid his true profession as a police officer from everyone so he couldn’t be judged by it.
He was liked by every person in the house and forged strong bonds with multiple alliances, though he was only true to one: his final two alliance. He was never nominated, and he won season 16 by a vote of 7-2 against his best friend in the house, who chose to take him to the finals out of loyalty.
5 Least Deserving: Adam Jasinski
As one of the more controversial players, Adam received flack for making disparaging remarks about disabled children on the show. And while he was a lot of fun to hang around with, he really can’t be credited with making any significant moves that would warrant the win. Regardless, he won Big Brother 9 by a vote of 6-1.
He endured some trials and tribulations post-show, including being sentenced to jail time after being charged for possession of pills with intent to distribute and failing to file a tax return for the year he won the big prize. Today, he says he suffers from drug addiction and bipolar disorder.
4 Least Deserving: Jordan Lloyd
Ok, you might be angry this sweet, innocent, lovable small-town girl is on the list. She certainly wasn’t a doormat and made moves and won competitions. But she seemed to hide behind, and focus on, her showmance, Jeff (now her husband), more than gameplay.
She was adamant that being laidback and kind was the way to play. (Sure, that makes you a great person, but does it make you a good Big Brother player?) She won season 11 mostly because she had a lot of friends in the house while the woman sitting beside her in the finals, Natalie, made a lot of enemies on the jury.
3 Least Deserving: Lisa Donahue
In this early win from Big Brother 3, the way the jury was handled is to blame for the more deserving winner losing out. Back then, the jury consisted of all 10 evicted houseguests, who had the chance to watch the back and current episodes of the show before voting. Any fan understands how this could be problematic.
Because of this, the bitter and spiteful jury voted for Lisa (depicted on the right) after seeing runner up Danielle’s cocky Diary Room confessionals. It was this decision, in fact, that led the show to change its jury process to include only the last seven evicted houseguests and keep them in a Sequester House so they couldn’t watch the show and have it influence their decision.
2 Least Deserving: Andy Herren
Sure, he was extremely likable and one of the underdogs. But Andy was also the very definition of a floater, shifting from one group to another as it suited him. He was even called a “rat.”
He didn’t start “playing” until long into the game and flip-flopped allegiances so much that it’s a wonder he still managed to stay under the radar. To many people in the house, however, he was just an extra vote. And maybe this was a strategy in and of itself. It didn’t hurt that he also won four final competitions in a row, then was officially voted winner of season 15.
1 Least Deserving: Josh Martinez
Best known for wearing his heart on his sleeve while also constantly banging pots and pans to annoy his enemies, Josh won simply because Paul, a returning player, was just too arrogant. Paul was so sure he would win after Josh brought him to the final two in season 19.
But the jury was more excited to see the look on Paul’s face when he came in second…again, even if that meant giving the win to someone they didn’t think deserved it. For what it’s worth, Josh did play hard, so he’s not totally undeserving. But between the two, Paul definitely played the better game. Too bad his ego got in the way.