Ranking The Big Brother Winners

From Eddie to Dan, and all the schemers in between.
'Chill Town' Will Kirby and winner Mike 'Boogie' Malin pose at 'Big Brother 7: All-Stars' at CBS Radford on September 12, 2006 in Los Angeles, California
'Chill Town' Will Kirby and winner Mike 'Boogie' Malin pose at 'Big Brother 7: All-Stars' at CBS Radford on September 12, 2006 in Los Angeles, California. - Getty Images
Charlie Toft

Big Brother kicks off its eleventh season this week, making this the perfect opportunity to look back at the first ten winners of the summer fixture. One thing they all have in common: at some point in any season, a player has to understand that these people aren't going to be your lifelong friends, much less lovers, so they have to be prepared to put the money ahead of a temporary relationship.

None of these ten were bad players -- they all won, after all -- but some had a relatively easy road to the crown, and others were the primary movers in making their success happen. Ranked from (relative) worst to first:

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10. Eddie, Season One: Eddie has to rate last due to the fact that Big Brother was almost strategy-free during its first season -- all a player needed to do was stay popular enough to win a viewer vote if he happened to get nominated. He still deserves mention for being one of the few people in reality TV history to announce flat out that he was playing the game to win money, and do so without making viewers resent him for it.

Annie Wersching

9. Adam, Season Nine: He turned out to be a pretty good guy in the end, despite early controversy over some jaw-dropping political incorrectness on his part. But this turned out to be a season filled with big personalities who were either completely unlikable or who did not make it to the end. Adam and Ryan, the two finalists, were a pair of amiable nonentities who needed limited strategic skill.

Annie Wersching

8. Mike Boogie, Season Seven: What is it about reality shows and their "all-star" seasons being won by people who hardly qualified as stars based on their original seasons? Boogie, who only got invited back to begin with because he was Will's mini-me, was carried along in his wake for most of all-stars, though he did win numerous competitions down the stretch and did a terrific job explaining himself to the jury.

Annie Wersching

7. Dick, Season Eight: This is the only season ever where the winner was also the oldest person in the game. Being the oldest is ordinarily a major social handicap in Big Brother, and I would give Dick bonus points for that, except for the help he received behind the scenes during the "America's Player" season, thanks to TV viewers who were fed a steady diet of Dick the lovable "rock 'n roll dad" and were spared the worst of his profane misogyny.

Annie Wersching

6. Lisa, Season Three: Lisa is probably the closest thing to an afterthought to ever win Big Brother, as she spent the entire game as a satellite member of two separate alliances, and ended up winning primarily because she was deemed less hateful than her endgame competition, Danielle. Not the most exciting player or blessed with much of a personality, but she had excellent survival instincts.

Annie Wersching

5. Maggie, Season Six: Maggie was the eventual survivor of what was the most bitter season of Big Brother ever, one where the alliances formed very early on and the two sides almost never acknowledged each other. In one respect, her win was simply a matter of keeping the numbers on her side, but she still managed to emerge as the leader of a group of disparate and headstrong people, and that took some ability.

Annie Wersching

4. Dan, Season Ten: Billed prior to the season as a conservative teacher from an all-boys high school, Dan proved to be more interesting than it first appeared he would be, and was willing to take the hits when it became clear he would have to disappoint some friends along the way. He ended up scoring a surprisingly easy victory over Memphis, who on the surface seemed to be the more ingratiating player.

Annie Wersching

3. Jun, Season Four: Jun and her runner-up Alison pioneered the idea of playing two alliances against each other until such time as they could team up to assume control of the game. Watching her play her hapless ex-boyfriend Jee, it was easy to see who the brains in the relationship was. Jun had her nasty side, but in the end, all she had to be was less hateful than Alison.

2. Drew, Season Five: He began his season coming across as an ingenue under the protection of older and louder male allies, but he proved to have surprising survival skills. His decision to latch on with the smartest person in the game (house girlfriend Diane) and the dumbest (Cowboy) paid off when he unemotionally made Diane the last person evicted from the house. Cruel, but it was worth a million for him.

Annie Wersching

1. Will, Season Two: No surprise here. In some ways Will Kirby is still the most unusual winner of any reality show ever: someone who went from gross egomaniac to last survivor of a hated alliance to the house jester to a runaway season winner, all in the space of a few weeks. Blessed with natural wit, he was the perfect person to spend three months with. Let's hope we're this lucky again this coming season.


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