All that seems relatively simple but it takes a lot of social abilities to be able to put it all into practice. Luckily for us, Will had social skills in spades and as we would find out throughout the course of Big Brother 2, he knew how to use them to his advantage.

Early on in BB2, Will is fairly low key on the strategy end. He establishes a bond with Mike and Shannon and Chilltown is born. Chilltown is not well liked around the house for its behavior. Thankfully for Will, Mike and Shannon are easily more disliked than he is, which is certainly not sheer coincidence from Will’s end. Of course he genuinely liked both Shannon and Mike but in the back of his mind, he’s also thinking that by virtue of being associated with them, they go before he does in any scenario. This buys him time when the house later decides to turn against Chilltown.

At this point in the early game, Will is worried about how the house perceives him knowing he is a doctor. He does not want his competition seeing him as the smartest guy in the house, something he highlights in a DR about the first impressions HOH competition. Because of this, he really emphasizes his vanity to the house guests, talking about how attractive he finds himself and constantly primping himself in the mirrors. Sure, the vanity is part of Will’s natural personality but it is the part of him he wants to show the house guests so that they forget about his intellectual side. We get an early DR about this which foreshadows the Will we eventually see down the road:

I hope everybody here has underestimated my potential for uh… for just massive destruction.

The earliest of Will’s mind games with the house is when he decides to bring up a communal 24 hour hunger strike. He talks about the spiritual benefits one gets from doing one and how he thinks the house should all try fasting. This is of course pure Will bullshit as he just wants to see how many of these guys he can get to do whatever Will wants. The entire house agrees to do the hunger strike. It is the first instance of us getting a DR from Will calling himself a puppeteer. He also gets extra insight on Autumn’s poor willpower when three hours into the hunger strike, she is unable to continue and whines to the entire house about it.

As Shannon becomes more and more unbearable to the non-Chilltown house guests, she is put up with Will by Hardy in week three. Despite having true affection for Shannon, Will ensures himself staying in the game by forming a bond with both Hardy and Nicole. Shannon also decides that she will sacrifice her game for Will by going ballistic in the house and using Hardy’s toothbrush to scrub the toilet. At this point, Will is not liked by the audience and seen more as a nuisance on the season more than anything. That doesn’t stop him from giving some solid DRs about his relationship with Shannon. Two funny ones in particular:

I consider her to be a sister. A hot sister I’m trying to hook up with but a sister nonetheless. I do have a message for her boyfriend at home… he’s outta here. It’s over for him. That’s completely done with.

There is something to be said that Will can be giving such cold hearted, douche DRs and still have a charming way about him. No other player in the history of Big Brother could be this mean and still amass such a large fan base. It speaks to his natural charisma that is unmatched in North American reality TV. It is around this point that Will also starts hammering the point that he is no threat to anyone. Everybody in the house dislikes him and no one will vote for him in the end. That line of thinking starts being repeated by others in the house and Will sort of starts settling into his underdog role.

The following week, Kent wins HOH and Will knows he is once again in trouble. Kent does not like Will for his association with Chilltown but he dislikes Boogie even more. Will, knowing he needs to secure his safety, brokers a deal with Kent. The latter will leave him off the block and if Will wins HOH the following week, he will keep Kent safe. This is a deal we will see Will make with Hardy and Krista down the road as well. It is a very one sided deal considering Will is never trying to win competitions as a way to further minimize his target and emphasize his general “incompetence”.

We also get during this time, a section on Will’s philosophy on house fun. He tells us in a DR that he participates in every house activity but makes sure never to win whatever they are doing. We get a great clip of the house playing Ouija and the board spelling out Jim. Will tells Nicole about his cousin Jim who died out on an oil rig in Thailand. Cut to a Will DR about him having a cousin named Jim who is far from being dead. That’s right Jonny Fairplay, your move was not the original, Will did this years before you ever lied about your grandma in the Pearl Islands. It is also with this DR that Will tells us what I have established as his second philosophy:

Are you familiar with the theory that the bigger the lie you tell, the more believable it is?

Those beliefs, hand in hand with Will’s natural ability to talk about anything, combine to make Will into the liar that he is. Most people should not go on a show like Big Brother with the plan to lie at every turn. They would come off as disingenuous and get caught by the rest of the players so quickly. Will is so good at lying that he is the exception to the rule and because he tells such grandiose lies, nobody ever thinks of questioning him on it. Even when they have their doubts about his honesty.

Needed a Chilltown GIF even if it’s not from BB2.

So Will loses his best friend Mike and is suddenly alone in the house. He vows revenge for his friends but plans nothing in the short term. Will knows that a direct attack at the Hardy and Nicole coalition would only weaken his long term game. This is another part of Will’s game that is inimitable unless you are born with his values and ability to disconnect himself from his emotions. Most players, given the chance, would fire back at the people who took out their friends. Even if that means making the island they are on even larger and solidifying a majority against them. That Will is able to delay his thirst for vengeance in order to give himself a real chance to survive in the house is impressive gameplay. Especially given that nobody had yet written the book on how to play Big Brother.

Instead of going out and trying to win HoH, Will joins forces with Hardy and Nicole as their secret partner by convincing them it is better to work with him now that he has no one and is not a threat. This brings us to the third tenet of Will’s game, his ability to connect with people. With Hardy, he gets in by talking about working out, both being into their own bodies and generally leading healthy lifestyles. With Nicole, he talks about fine cuisine that no one else in the house likes or would be willing to discuss with her. An example of that is when Will mentions missing Japanese cooking whereas the rest of the house wants burgers and fries and Nicole excitedly chimes in: “A sashimi plate!” Of course with Shannon and Boogie it’s the ability to let loose and have fun. In the late game, we see this ability again when he bonds with Bunky over their shared “sentimentality” and Bunky calls Will a sweet guy. Short of it all, Will knows what makes individuals tick and adapts himself to fit in whenever necessary. He is the definition of a social chameleon.

The first week post-Boogie, Hardy wins HOH and nominates Will as a pawn next to Kent. This angers Kent because he had a secret alliance with Hardy, Krista and Monica, something he tells Will. The good doctor takes this information to Krista who stupidly confirms it with him. She tells him not to tell anyone because no one else knows but of course, Will does no such thing and he goes right to Nicole in order to build trust with her and also break down some armor in the Nicole/Hardy dynamic. He makes up a lie about Monica, Krista and Hardy sitting around pretending to play cards and flipping cards over to indicate who goes home next. Another big lie that people should question but don’t. Nicole buys it hook, line and sinker and now believes that Will is her sole ally in the house.

Of course, blowing up the secret alliance makes a few people mad at him. This includes Monica who is not one to control her temper. To do some damage control, Will comes up with a brilliant plan. Remember when Derrick held a house meeting in order to deflect a bunch of blame onto Zach? Yeah well Will did it first to Hardy and Monica who proceed to get into a verbal fight in front of the entire house as Will sits there picking his feet and staring off into the sky.

The one human moment we see from Will is losing Krista. She is his last friend in the house and he can’t give her a sympathy vote. He truly feels like a coward for this and sheds what appears to be genuine tears over it. Then again, Will could be lying in the DR about the entire thing and using it to his advantage. I say this because his tears bring him close to Bunky and he also takes the time to make sure Monica sees him crying so that he appears weak. While Will feels bad to lose his friend, he also recognizes that it’s game on for him:

Now there’s no one left in the house that I like so we can begin anew and let the games begin.

As the chaos of being in the house starts to set in for everyone, Will drops us another little nugget coming from his DRs:

I know everyone in this house is evil. I’m just the only one who can admit it.

That’s Will’s final tenet and one of his bigger ones. Being able to find what causes individual housemates to break and show their dark side is Will’s elite skill. Knowing how to bring it out, expose it and then make the other person feel bad about it is exactly how Will can shame people into doing his bidding. We will see him doing it to Hardy and Bunky when they both accept deals for money in exchange for putting the house on peanut butter and jelly sandwiches and we see him do it to Nicole constantly throughout the season.

Once again, Hardy wins HoH and puts Will up on the block. However, he goes up but is the pawn because he makes Hardy laugh and Hardy feels like they are friends. Hardy feels closer to Will than to Bunky and this costs Bunky his life in the game. Will also makes a promise to Hardy that he will keep Nicole safe were he to win HoH. They are getting to the final four and they still have not realized that Will is actively losing competitions to avoid going back on his “deals”. With his promise to Hardy, Will also drops a quote in the DR that I feel completely describes Will’s BB2 game. It’s the one that has stuck with me more than 15 years later:

I would stab them both in the back and leave them to bleed on the kitchen floor and I wouldn’t even clean it up. And if I did, I’d use a dirty towel and leave it on the bathroom floor.

Once the game hits Final Four, Will is basically an unstoppable force. He openly throws the HoH to Monica, knowing she will put up Nicole and Hardy because who would want to go to the final three with a pair? He then gets to cut Hardy like he said he would weeks ago but not before making Nicole sell Hardy down the river so that she begs for her life… just for the fun of it. Nobody said Dr. Will was a good person. Just an entertaining one.

At final 3, he tells Nicole he will try to win HOH but of course, that’s a lie. Nicole has to win it instead to avoid elimination and is forced to evict Monica because she knows she would never beat Monica in the final 2. That is all part of Will’s plan to ensure Monica’s vote because as she leaves, she is absolutely livid with Nicole.

One of the most interesting things about Big Brother 2 is the dynamic between the two finalists. Early in the game, Nicole and Will are at odds. Nicole is a tight ass and Will is kind of a jack ass. Nicole starts on the bottom and narrowly avoids being the first out but she slowly gains power as Will falls to the end of the totem pole. Recognizing that he needs to be social with her to survive, Will starts trying to make bonds with Nicole and their relationship is… odd to the say least. Over and over again, Will tells Nicole he won’t do something and then goes out and does it. Nicole then gets angry at him but eventually forgives him and gives him another chance. Rinse, lather, repeat until Will wins half a million dollars.

As their relationship evolves, Will keeps telling Nicole she’s attracted to him and that she’s in denial. Keep in mind that Nicole is married. To prove Will that he is so totally wrong, she follows him in the shower and starts undressing like she’s going to join him, all the way to taking off her pants and opening the shower door to see a totally nude Will. She also often takes the time to shave his body, since Will is averse to body hair, which always struck me as something fairly physical and intimate. There is also the hot tub incident which I won’t elaborate on because we lack details but something happened there.

Behind the scenes, in his DR, Will was brutal to Nicole. He disparages her and she was the butt of pretty much all of his jokes. The way he played with her head also sent her into an emotional tailspin and by the end of the game, she was a complete mess. It made her the perfect person for Will to bring to the finals because she had no chance to form coherent arguments and was unlikable for her crabby behavior in the house. Will took Nicole on in psychological warfare and completely shattered her.

That’s just the game side of things though. What makes Will a truly great character is his natural abilities in front of a camera. Some people try to be funny or charming, Will just happens to be both from birth. He is far and away the most quotable player on his season and whenever he is not on camera, the season suffers from it. Some highlights from his time in the house:

• In one of his first speeches to the house on eviction day, Will uses the time to quote Gloria Gaynor’s “I will Survive” and gets the whole house breaking into the song as Julie Chen awkwardly tries to handle the situation.

• Just his general relationship with Julie and how he completely throws her off by just being himself.

• Will’s relationship with Ophelia the pig. He’s her primary care taker, he saves her from drowning and likes to use her for a lot of his jokes.

• The house getting a trampoline through America’s vote and Will losing his god damn mind over it “TRAMPOLINE! TRAMPOLINE! TRAMPOLINE!”

• The boy band he, Boogie and Hardy create.

• Will hitting Nicole with a RV Car, sending her on another meltdown and then apologizing to her while basically laughing in her face about it.

• Will making Nicole’s doll for her, giving her nipples and a thong and pissing off Nicole. This nearly causes Nicole to decide to vote him out instead of Bunky before Will massages things over yet again. Few people played more dangerously with their stock in the game than Will in Big Brother 2.

• When the Survivors come to visit, Will making light of their situation by comparing it to his blisters and being forced to go from the hot tub to the pool.

• Will’s total embracing of the giant Peanut Butter jar he won in the final four HoH comp that he threw, much to Hardy and Nicole’s anger because it left them out to dry.

These are all without even considering Will’s classic DRs. So to end this writeup, allow me to give you Will’s 10 best quotes from inside the Big Brother house during BB2, in no particular order.

About Hardy’s crying over nominations:

Hey maybe no one will notice except 100 million Americans.

Upon receiving Ophelia:

We got a pig today and the first thing I though was what about the bad manners, the smell and the gross hair? And then I realized you know what? If I can deal with Bunky and Kent, I’m sure the pig can deal with Bunky and Kent.

About Monica’s interesting way of phrasing things:

When Monica says it’s on it might mean that the light in the living room is on or that she might punch you in the face.

As everyone talks about the emotional things the money could help them with, like Monica’s dad’s debt or a tombstone for Krista’s mother:

I’m going to buy gold chains for my friends, a jet ski, jewelry, pork bellies. Just good solid investments.

On Nicole’s body insecurities:

When Nicole got on the scale and it told her she gained four pounds, Bunky and Hardy told her it was muscle. WHAT?! Its FAT! It’s fat. PS: you’re getting fat.

As Hardy starts turning into a dark character:

As far as I can tell, Hardy is turning to the dark side. He’s dyed his hair black, he got these bags under his eyes and now he’s smoking cigarettes.

On Will and Nicole’s dynamic:

Nicole and I don’t have much in common but the one thing we do have in common is that we are both attracted to me.

After winning his only competition of the summer:

“I was considering donating this trip to someone else in the house who has been a little more depressed like Nicole… just kidding!! I’m keeping this trip! I’m not letting anyone else use it. Of course I wanna ride in a helicopter and no one can take this from me”.

One of his many fun interactions with an awkward Julie Chen, this one on the phone for the peanut butter offers:

“I can’t go to dinner with you Saturday, I’m in a serious relationship!”

Describing the Nicole doll he made for her:

This is a doll that Nicole asked me to drop off. What it really is is a very angry woman, she has one eye that’s a piercing eye. It’s used mainly for finding dirty towels on the floor. Also, it’s used to finds kids who are having fun and yell at them. (in Nicole voice) Pick up your towels! No one’s allowed to talk! I’m freaking out about everything! Will, don’t have any fun! Don’t have any fun! Don’t have any fun! These arts and crafts are bullshit! I hate them, I’m not doing them, I’m way too advanced for this, I’m not doing anything blah blah blah.

If you haven’t seen the season in a while Big Brother 2 is worthy of a re-watch. It may be slower paced in comparison to what is currently happening on modern Big Brother seasons but it doesn’t matter. They have some great casting choices and the crown jewel among them is Will. Maybe you’ve forgotten why he is so appreciated in the Big Brother community. All it takes is a few episodes of BB2 and you’ll go right back to remembering his legend.