Look at the people getting this one right. For all the moronic governors, members of Congress, and former presidents that who been elected but have nothing better to do than make their constituents’ lives worse — but still win by tapping into those tried-and-true methods of racism, misogyny, homophobia, and transphobia — the public is on the right side of history this time.
Sidney Deane and Billy Hoyle for the Fictional Hoopers Championship. Did the committee set the entire bracket up for this to happen? Of course we did! But see, when we gerrymander it’s not just for our benefit. It’s for everyone’s. White Men Can’t Jump is quite possibly the greatest sports movie of all time. Every character, from Gloria, to George, to the Stucci Brothers, to Marques Johnson’s sensational performance as the loveably deranged Raymond, hit every note to create a glorious symphony of basketball, toxic relationships, and capitalism.
The stars of this grand opus, Wesley Snipes and Woody Harrelson. The Academy actually put them and Rosie Perez on stage for a reunion at The Oscars, because, as always, the Academy is decades late in giving people their due for great performances. So hit up @Deadspin on Twitter one more time to vote for your favorite between Sidney Deane and Billy Ho.
Also, since this intro was started with an election metaphor, we’re ending this tournament presidential-debate style.
1. Let’s start with a simple question. Since this movie is about basketball, there’s a lot of winning and losing — regardless of Gloria’s ambiguous definitions of what is actually a win, a loss, or a tie — the question for both of you is why did your character win the movie?
Stephen Knox: The movie starts with Billy, it ends with Billy, it centers around Billy. We get to explore his redeeming qualities and his bad ones, and let’s be real, the redeeming qualities are few and far between. He has a terrible temper that cost him all of his money multiple times and damn near his life. Billy is also quite racist. Sidney absolutely should’ve taken his money after that unprovoked and repulsive “a Black man wants to look good first and win second,” comment. That’s the second time that he said that in the movie, and the first time it was accompanied by a, “how many dinners did this chain set your family back?” Not to mention how mean and controlling he can be with Gloria, even though she stays with his dumbass after repeatedly losing all of their money, and putting her life at risk, too.
But there is also the endearing side of Billy. The open-hearted buffoon that you want to root for. The guy who didn’t hesitate to put his car on the line to get Gloria on Jeopardy!, or the fact he actually called Sidney a good guy after clearly getting hustled for his life savings. That’s the Billy that you hope gets it right. The guy who you just shake your head, and say “Poor stupid bastard, I hope he gets it together.” The good, the bad, and the ugly, it’s all there with Billy, and he makes you feel it. The movie is his even if it’s Sidney who actually gets everything he wants.
Sean Beckwith: Sidney won the movie because he was the better hustler. Despite Billy being a better team player and shooter, and getting the best of Deane early in the movie, Sidney returns the favor, and only gets caught because Gloria sniffs out the scam. Also, not only does Deane “listen to the woman” in his house, he’s taking her out of the ain’t-no-vista-of-no-view apartments and presumably into a house.
I thought it was clear who won the movie. Gloria left Billy, and Billy had to give all of his winnings to the token goons pursuing him over some unseen scheme gone wrong. Yes, he proves he can dunk, but only off an alley-oop. That’s one step above “guy who can only dunk a tennis ball but tells you he can dunk” in the pantheon of guys who tell you they can dunk but don’t tell you there’s a caveat.
Affably gullible and good-hearted aren’t what Ringzzzz culture demands; winning requires a smart, cut-throat, no-honor-amongst-hustlers approach. Sidney loses twice in the movie, and once was on purpose. Billy Hoyle has three Ls in his name alone, and by the time the credits roll, it’s evident that the label “loser” will follow him until he sorts out his priorities.
2. We’re dealing with a couple of hustlers who were duplicitous in many instances during this movie, but hey this is America. Like Wesley Snipes said in New Jack City, “You gotta rob to get rich in the Reagan era.” Since that statement can apply to any presidential term, the question for you two, is why is your character the most likable?
SK: I mean, come on, who doesn’t love a good dope. We watched Jerry Springer and Maury to feel better about our own family drama, and dopey main characters are a nice ego stroke. When it comes to dopes, few are dopier than Billy Ho. If you pinned a dollar on Billy’s shirt, he’d lose the shirt. We all have friends who are terrible with money — and if you don’t, then you need to make an appointment with a financial adviser immediately — but hopefully not like Billy. I can’t even call him a gambling addict because he doesn’t go to casinos or shoot dice in Venice Beach alleys. He just plays basketball, bets with his heart instead of his head, and writes terrible love songs to convince Gloria that she should continue to waste her life with an idiot.
What’s not to love about this guy? He’s the perpetual underdog every time he takes the basketball court and puts in work. The guy is a true hooper, and who doesn’t love a good underdog basketball story? And he can even talk a little trash. He’s the only person in the movie who can make Sidney lose his cool, and Billy really twisted the knife early on by letting Sidney know he was getting hustled and throwing that country club comment back in Sidney’s face. He’s not 100 percent dumbass, but he’s enough of one to make viewers feel better about themselves while also being entertaining.
SB: Winning a popularity contest against a guy who is intentionally goofy and then, voilà, he can hoop is impossible. Billy is supposed to be charismatic. He’s a lovable, dopey white guy who has a propensity for self-destruction. I know a ton of Billy types; I’m one of them.
I can relate with Hoyle, but I look up to Sidney. Having your shit together — or holding onto your wife who has her shit together and mandates that you have your shit together, too — is commendable. Liking and listening to your significant other is the kind of relationship we all should aspire for.
I acknowledge that my candidate’s wardrobe somehow aged worse than his competitor. That said, the ’90s are making a comeback. I saw multiple college-aged ladies with Jnco-esque jeans and/or Doc Martins out over the weekend, and if those pass as retro these days, then hiking your shorts up dangerously close to your belly button and then tucking a loose-fitting, pec-accentuating tank top into it is idiotically ironic enough to qualify as high fashion. Deane wore a cycling hat, just like Will Smith sporting a similar one in the intro to Fresh Prince of Bel-Air.
The only people who bought parental advisory shirts were teenagers with an affinity for Hot Topic and too much allowance. Also, in order for the current youth to even understand the concept of sticking a disclaimer on a CD jacket, they’d have to know what a CD jacket is.
3. Through all of the basketball played in this movie, the one matchup we did not get to see is Billy against Sidney in a real game of one on one. Why would your character be triumphant in that matchup?
SK: Billy would sit on that stupid behind the back layup that Sidney does and snatch it right from him. Then he would whisper a smart aleck remark in Sidney’s ear, and at that moment the game would be over. Sidney would try to play it cool but he’d be livid and start missing, just like he missed that jumper in their shooting contest. Of course Sidney has the athletic advantage, as kindly pointed out when testing the rim for Billy during his absolute personal worst — yet highly entertaining — five minutes of the movie when he lost a four-figure come up, and ride, after a racist comment.
Still, even though Billy is less athletic, he moves better than Sidney does on the court. Those assists in that very first game show that he has a real feel for the rhythm of basketball, something that Sidney never showed. It would be hard work for Billy Ho to take down this matchup. But in the end he’s just a better basketball player than Sidney Dean.
SB: The only qualm I have with White Men Can’t Jump is the directors depriving us of what would’ve been the best post ending scene of all time. They wouldn’t even have to do it like a Marvel teaser, rather just run wide-angle footage of Sidney and Billy going head to head next to the credits like a blooper reel. Set up the camera so it feels like we’re watching from the bleachers, hit record, and hope Wesley Snipes and Woody Harrelson don’t look too embarrassing playing actual basketball.
We were never going to get that though because the facade would’ve been exposed. A 5’ 9” guy and a 5’ 10” guy failing to come anywhere close to dunking would’ve destroyed the entire premise of the movie. As far as who wins a theoretical game between Hoyle and Deane, it’s Sidney. Billy took the initial game of glorified horse because he played dumb, and Sidney’s game is about athleticism. What makes Billy so good is his passing and shooting. Well, if he has no one to pass to and can’t shake Sidney to get open looks, he’ll have to rely on a ton of pump fakes and guile the way Kobe did after his burst left him. Now that Billy has lost the element of surprise and Sidney has the book on him, Sidney wins seven games if they play 10 of them.
SK: Billy Ho is a classic American character. Raised by a preacher, but goes out into the world because he wants something different, and finds out just how hard and cold the world can be. College didn’t work, so he started hustling. The man has talent, but he’s one of those people who always reacts, but rarely thinks. That’s how he found himself with gangsters chasing him and pissing away money like a bar patron on beer No. 9. Life could be easier if the man would humble himself, but instead he allows everyone else to humble him. Every single time he feels that his pride is under attack he makes costly mistakes.
However, it’s his flaws that make him compelling. He’s out there scratching and surviving, and in the process landed a really hot, smart girlfriend that he absolutely does not deserve and he knows it. Yet, he’s out there every day with that chip the size of his convertible on his shoulder. Billy can’t get it right, but bless his heart, he gets up the next morning and tries again with the small bit of charm and talent that he was gifted. So even though Billy is not able to hear Jimmy, there’s a reason he was the No. 1 overall seed in this tournament. He has it all, the jokes, the game, the woman, the likability despite having very few likable qualities. Billy Ho is a true American tale, and that’s why he’s the best fictional hooper. Though there is that racism shit.
SB: After 62 games and five rounds, we should’ve just done an article on who was better between Billy Hoyle and Sidney Deane. It’s not shocking that this is the final we ended up with in a field of so many fictional hoopers. White Men Can’t Jump really is a perfect movie. There are so many layers to it, the leads have irrefutable chemistry, it’s funny, it’s heartbreaking, it’s polarizing, and the use of basketball as an allegory about race is fucking brilliant.
It’s for the best that we never saw definitively who would’ve prevailed in a game of one-on-one because that would’ve vaulted one man’s philosophy ahead of the other’s. Both of these men are flawed individuals — Billy puts basketball above all else, including Gloria, and the only person Sidney won’t hustle is his wife.
However, for all his faults — taking Billy’s money by betting him he can’t dunk is so cruel — who comes out on top monetarily and personally? Sidney is getting out of the sticks and taking Rhonda with him. Billy is broke and alone. Looks like you can look good and still win.