We spent six weeks rewatching every movie about basketball. We did this because we are just (slightly) larger versions of children, but also because we wanted to figure out who is the best fictional basketball player of all time.
This is a more overwhelming task than it would appear to be. To organize our research, we needed rules. They are as follows:
Rule 1: You can’t pick more than two players from any one movie. This is the Blue Chips Rule. Blue Chips was loaded with actual players. In a movie-vs.-movie basketball tournament, Blue Chips waxes everybody.
Rule 2: If someone has played a basketball player in more than one movie, you can pick only one of his or her roles. For example, Marlon Wayans was in The Sixth Man and Above the Rim, and he played basketball in both. You could pick him for only one of those performances — though we can’t imagine anyone would ever, ever, ever pick Marlon Wayans twice for anything.
Rule 3: You can’t pick anyone who was portraying a real-life basketball player. That’s no fun. The legend’s already been written. This is the Earl Manigault Rule.
Rule 4: There is no restriction on the type of movie referenced. It doesn’t have to be described as “a basketball movie”; it only needs to contain some basketball scenes. Remember when Rufio played halfpipe basketball in Hook? Remember when Jim Carrey broke the backboard in The Cable Guy? Remember when John Tucker did that flip dunk in John Tucker Must Die? It’s all up for grabs. This is the Fletch Rule.
Rule 5: This is not a Who Was the Best Basketball Player thing, this is a Who Was the Best Fictional Basketball Player thing. That means acting has to be considered. Of all the eligible players, Shaquille O’Neal was very clearly the best player (Michael Jordan in Space Jam is disqualified because he was playing himself). If it were a straight basketball measurement, he’d have landed at no. 1. But he’s about as good an actor as a tree stump wearing sunglasses is, so he did not land at no. 1.
Before we get to who made it into the top 10, some awards:
Jason: “I’ll make it.” Jimmy Chitwood. There is nothing else to say.
Shea: There’s actually a lot more to say, because this is not the best monologue from a basketball movie. The best monologue in a basketball movie isn’t even given by a basketball player. It’s given by a coach. And guess what? It’s TWO best monologues, from the same character — the best two kinds of monologues there are.
The first: This one is from the beginning of Blue Chips, and it’s Nick Nolte just losing it:
He obliterates everything. He does the leaving-the-room fake-out move on the team TWO TIMES IN A ROW. He touches on all the modalities of destroying someone, transitioning from MAD ANGRY to FIRE ANGRY to DISAPPOINTED ANGRY to SAD ANGRY to SUPER-FIRE ANGRY, then finishes it off with SUPER-DISAPPOINTED ANGRY. When I was watching it the first time, I swear to God everyone in the movie theater — we all just got up and started running wind sprints.
The second one: This is from the end of Blue Chips, and he gives it at a press conference after he’s become completely unraveled.
Amazing. This is somewhere near the top of the Movie Press Conference list, likely either right before or right after Al Pacino’s end-of-movie press conference monologue in Any Given Sunday. This is the quiet monologue.
Pick either one of those. Tell Jimmy Chitwood to GTFOH.
Jason: Jimmy is a man of few words and many baskets.
Best Trash Talk
Jason: It’s Cold Crush vs. Fantastic Five in Wild Style.
Let’s be real: The best basketball movie trash-talk scenes ever happen in White Men Can’t Jump. Trash talk in WMCJ is funny and cutting and mean, without being actually offensive. No small feat!
So I’m going to go a different way. My choice is the rap battle — which, technically speaking, is just trash talk with more structure set to a 4/4 meter — between Cold Crush and Grand Wizard Theodore and the Fantastic Five in 1983’s seminal Wild Style.
Shea: You’re right. The trash talk in White Men Can’t Jump was transcendent. So we’ll skip over it here. If we continue with your “mean without actually being offensive” criterion, then this award would go to Philip Seymour Hoffman in Along Came Polly. Because him shouting “Raindrops!” while shooting will never not be funny.
But I don’t like “mean without being offensive.” I fall in the opposite camp. Mean while being mean is an especially wonderful kind of trash talk, and so that’s why this category has to belong to Tupac in Above the Rim.
He played Birdie, and he was just so devastating. Birdie turned mean into an art. He bullied everyone in the movie, but nobody suffered as much damage from his thundercock of maliciousness more than poor, poor Bugaloo. Here’s the most unsettling scene:
If you’ll recall, Bugaloo ends up shooting Birdie at the end of the movie. I think that’s the best evidence that your trash talk got to someone.
Best Thing That Happened on a Court That Wasn’t a Basketball Game
Jason: Zero Dark Thirty. On a dusty, dirt-choked, makeshift basketball court somewhere in Afghanistan, Navy SEALs, acting on intelligence developed by the CIA, made the final preparations for their raid on Osama bin Laden’s Pakistani compound. I’m going to go ahead and say this cannot be topped.
Shea: Dang. Bodied. I was going to say when Jason Statham fought those dudes and stabbed that basketball with that Godzilla knife and then rode off on a motorcycle in The Expendables, but this is probably better.
Best Game Played
Jason: It’s Jesus Shuttlesworth vs. Jake Shuttlesworth in He Got Game. Just think about the stakes: After two hours of highly imperfect buildup, Jesus finally squares off against his jailbird dad, who’s back in his life only because he needs Jesus to sign a letter of intent to Big State University. For Jesus, this game is about finally taking agency in his own life, when everyone in the world, including his father, wants to take a piece of it for themselves. And, it’s about beating the man WHO KILLED HIS MOM in a game of one-on-one.
Jake is playing for his freedom; if Jesus doesn’t sign, it’s back to crafting shivs out of melted shoelaces and bartering with cigarettes. More than that, he’s playing for pride; no father, in history, has ever been OK with losing a game of one-on-one to his offspring — and that’s without the threat of continued incarceration hanging over his head if he loses.
Apparently the script called for Jesus to win the Oedipal showdown 15-zip. Denzel, who played college ball under P.J. Carlesimo at Fordham, had other ideas and scored the first basket, eventually running the score out to 4-2, Mom Killers. My favorite anecdote about this scene is that Ray tried to call cut when Denzel started scoring. According to director Spike Lee:
So, Denzel had the ball first and he made a couple of lucky shots and Ray called, “Cut. Timeout.” He says, “Wait. The script says he’s not supposed to score.”
OK, STEVEN SPIELBERG. WHY DON’T YOU JUST LEAVE THE MOVIEMAKING TO PEOPLE WHO KNOW WHAT THEY’RE DOING AND STOP GETTING SCORED ON BY AN ACTOR?
Shea: Four things here:
1. You think of Ray Allen now, and you think of this:
But back then, his NBA rep didn’t overshadow the character of Jesus Shuttlesworth. I think a big part of that is because Ray was still with the Bucks in 1998, so there were only, like, 15 people who knew he was actually in the NBA and not just some tall actor.
2. This game was poetry. The two best parts: When Denzel hits that goofy layup early in the game and then takes a victory lap around the 3-point line, and Ray just stands there watching him and seethes. Later, when Ray bodies Denzel down low and then tells him, “I thought you lifted weights in Attica.” What a great jab. I remember the last time I played my dad in basketball. It was half as athletic as Ray and Denzel, but just as contentious. Near the end of the game, he was pressing up on me, so I stepped back a bit, bounced the ball between his legs, ran around him, caught it on the other side, then dribbled in for a layup. That was 16 years ago. I don’t think we’ve talked since.
3. One of the reasons this scene is so compelling is because you get to watch a guy who is not a professional basketball player square up against a guy who is. Every NBA fan has asked themselves, “How well would I do against an NBA player in a game of one-on-one?”
4. HOWEVER: I love the Jesus vs. Jake scene, but I have to give the Best Game Played title to when Sidney and Billy played Flight and Willie in the final of the Two-on-Two for Brotherhood Basketball Tournament. I’m gonna talk about this a bunch later, though.
Most Devastating Thing That Happened in a Basketball Movie
Shea: I have two, even though only one of them is applicable. The first is when Cornbread was shot by the police in Cornbread, Earl and Me. The second one happened in Fresh, which was more about chess, but featured scenes that took place on a basketball court, and that’s where the devastating thing that I want to mention happened.
Without getting all the way into the movie’s plot (which is especially tricky), there’s a 12-year-old boy who has a crush on a girl. There’s this scene in which the boy and his buddy are out on a basketball court, and the girl is there too. There’s a basketball game happening away from the three of them, and one of the players in that game is a very aggressive drug dealer. He feels disrespected when one of the younger players shows him up, so he takes out his gun and shoots him in the chest. The camera pans out, and right there — oh man, I can barely even think about it. Right there, lying on the floor, is the little girl the boy had a crush on. She took a stray bullet to the neck. It’s just the worst. The worst of the worst. I can’t even. I don’t even want to try to find a clip of it.
Jason: I have nothing else to add.
Best One-Two Punch
Jason: Since we have to prevent this from being a White Men Can’t Jump hagiography, I’ll go with a blind Chris Pine and his best bro Pooch Hall, straight hustling fools in H-O-R-S-E in the rom-com Blind Dating, which is like a genre mash-up of At First Sight, Mississippi Masala, and The Graduate. I call this scene “White Men Can’t See.”
Shea: “White Men Can’t See” is the best fake title. There should be a whole “White Men Can’t … ” spinoff series. George Clooney, born deaf, plays the coach of a basketball team at a tough inner-city school in White Men Can’t Hear. Brad Pitt plays a disabled war veteran who lost his hands in the war and takes up basketball at the rehab clinic and learns to love again in White Men Can’t Hold. Matt Damon plays a man born with a rare disease called notastebudiosis that renders his tongue useless in White Men Can’t Taste. And then there’s a team-up movie with all three of them together like the Avengers, and they play in a three-on-three tournament to rescue the president’s daughter. That one’s called White Men Can’t Do a Bunch of Shit. I’m in. I’m all the way in. I’m watching all of those.
Jason: It’s David (Michael Fassbender), the android from Prometheus, hitting hook shots in outer space while riding in circles on a bicycle. There aren’t a lot of in-game applications for a move like this, I grant you. Still, we’re talking legit 3-point depth while on the move and operating a vehicle. With a good screener, this move is essentially unguardable. You cannot get more advanced analytics than those measuring an artificially intelligent robot shooting efficient 3-pointers. This is what Daryl Morey dreams about instead of electric sheep.
Shea: For real, I just watched that clip for an hour straight. Great as it is, though, I feel like I should advocate for a real-life version of that shot, which is what Sigourney Weaver did during the Alien: Resurrection shoot.
Watch Clay Morrow’s face in the bottom right corner of the screen when she makes the shot. Nothing has ever made me happier than watching him break character right there.
Most Likely to Actually Know How to Play Basketball in Real Life
Jason: Every single dude in Blue Chips. Seriously, look at this cast. In addition to Shaq, there was Penny Hardaway, Matt Nover (Indiana University and a bunch of teams in Portugal and Spain), Kevin Garnett, Bobby Hurley, Calbert Cheaney, Keith Smart, Allan Houston, Rick Fox, Chris Mills, and many, many more. I realize this is kind of cheating, but, c’mon. No-brainer here.
Shea: One hundred percent cheating, Jason. The answer here is Duane Martin, who played Kyle in Above the Rim, Willie in White Men Can’t Jump, and a security systems salesman in Boys II Men’s “I’ll Make Love to You” video:
Also, another guy is probably Tom Cruise. Here’s his basketball scene in Cocktail:
He hits seven 3s in a row, the sixth of which is a hook shot, and the seventh of which he shoots behind the back. I remember reading this thing about how Cruise put a pool table in his apartment and trained for months for The Color of Money. I wonder if he put a hoop in his backyard before Cocktail. Tom Cruise is beautiful. I’m going to miss him whenever he ascends into an alien ship.
Least Likely to Actually Know How to Play Basketball in Real Life
Jason: There’s approximately zero percent chance of any breed of dog ever successfully competing in an organized basketball game, much less actually scoring a basket.
Shea: Whoa. I guess you’ve never seen the Puppy Bowl then, Jason?
If we’re at the park, and all the people from all the basketball movies are there, and we start a pickup game, and you and I are picking teams, Air Bud’s gonna show up on someone’s team near the end of the draft, but he will not be the last one picked. You know who the last one picked will be? I’ll tell you who will be the last one picked: Josh motherfucking Hartnett from O.
The Top 10 Fictional Basketball Players
10. Jimmy Chitwood, Hoosiers
Jason: Jimmy Chitwood. The name itself evokes the susurrus of endless fields of golden Indiana corn swaying gently in the breeze of God’s own breath, with the sun — ripe and red — setting on another bountiful Midwestern day. “Jimmy Chitwood,” whispers the stalks as evening gathers in their lengthening shadows, merging with those of the silos and barns.
All the hours here in the palm of Eden’s hand, from dawn to the deepening dim, are marked by a couplet of sounds that, hand-in-hand, beat out the metronomic and immortal pulse of the land.
Bounce. Swish. Bounce. Swish. Bounce. Swish. Bounce. Swish.
It is the Chitwood, and the Chitwood is the land.
Men, strong men, who fought in places far afield and returned to plow the land and whose pride is as undilutable as the atom, grow silent when the Chitwood passes by.
Women, strong women, who sustained the hearths and stood sentinel at every resting place from crib to coffin, beam with silent pride that among them is one who nursed this child, this man, this Chitwood.
Into this place came Norman Dale, the worst, most boring-est, play-the-right-way son-of-a-bitch garbage coach in the entire state of Indiana. “I want to see four passes before every shot,” says the worst coach ever, whose offense is so tedious that people who spend every minute of their empty lives watching corn inch ever skyward are mortally offended by its pure shittiness, and resolve to drive Norman Dale from his post and their town.
But it is the Chitwood, his hair swept back with the motor oil from a thousand broken-down tractors, who stays their hands, and whose words strike with the force of thunder above the eaves when he says, “Coach stays, I play. He goes, I go.” The men and the women of the town murmured their discontent but could do no more. The Chitwood had spoken and his words were as timeless and true as Orion’s great belt.
And how did Norman Dale, the worst fucking coach who ever walked the face of God’s earth, show his gratitude to the Chitwood, whose bounce-swish-bounce-swish carried the team, Norman Dale’s team, against all who opposed them and whose words restrained the townsfolk from chasing the coach through the night at the points of their farm implements? By trying to give the last shot of the state championship, the sacred game winner, to Buddy Long. Who the fuck is Buddy Long?
Shea: Did I just fall inside a Norman Rockwell painting? What TF just happened? That was beautiful. I feel so American right now.
Sidebar: What a terrible, terrible play call at the end of Hoosiers. “Hey, here you go, here’s the ball, Jimmy. Just stand there for, like, 20 fucking seconds, then shoot a contested jumper. Good luck, bro.” I gotta believe Hoosiers is Scott Brooks’s favorite movie.
9. Jim, The Basketball Diaries
Shea: I’m going to toss three things out here:
1. I cheated here. I broke Rule 3. I’m sorry. It’s just if I have the opportunity to talk about a movie in which someone masturbates on a roof, then I’m going to take advantage of that opportunity. Sorry. I’m sorry.
2. There was Pre-Junkie Jim and Post-Junkie Jim. Post-Junkie Jim is playing in the video above. I’m specifically talking about Pre-Junkie Jim here. He was a basketball panther. He was super-skinny and slight, but so is Kevin Durant. Pre-Junkie Jim is White Kevin Durant, and you’re crazy if you think I’m not buying up all of that stock.
3. Michael Rapaport played a skinhead in two movies … IN 1995.
8. Neon, Blue Chips
Jason: Blue Chips is the story of how the coach of the fictional Western University resuscitates his team by subverting NCAA rules. Shaquille O’Neal essentially plays himself while everyone else in the movie has to call him Neon. Neon Boudeaux is from Louisiana; Shaq went to college at LSU. Neon scored 520 on his SATs (960 after tutoring); Shaq scored 780. Neon left school early for the NBA; Shaq is Neon.
Neon basically dunks everything. He’s unstoppable. His shooting percentage is probably something in the low 80s. When Western’s coach needs a play out of a timeout with 12 seconds left in the game to beat no. 1 Indiana on national television, he goes with the dude who has literally not missed a shot for the entire movie, ShaqNeon Boudoneal, for the game-winning dunk. I’d put him higher, but Blue Chips was Shaq’s first movie and the subsequent damage his film career has done to humankind is pretty much beyond measure.
Shea: This feels way too high for me, but I’m willing to concede that I might feel that way because I just don’t think I can ever forgive Shaq for trying to ruin Inside the NBA. God, he’s the worst. He’s like if a bowl of oatmeal could talk. I need Shaq to sit on top of a missile and then I need that missile to be shot straight TF to Neptune.
7. Shorty, Sunset Park
Shea: He is super-quick, fearless, invested in winning, and had a super-big heart and just the right amount of craziness. He’s the movie version of Allen Iverson.
Fredro Starr had the best bone structure of anyone in the ’90s. I’m not sure how he’s gone so underappreciated as an actor. I mean, I understand that he has only one note, but he plays the shit out of it.
Also, when he was in The Wire, his nickname was Bird. Tupac’s nickname in Above the Rim is Birdie. All of a sudden I have a lot more respect for birds, bro.
When Shorty’s team loses in the championship game, that was one of the first times I ever had my heart broken by sports. I just didn’t understand why anyone would make up a story and not have the guys who were supposed to win at the end actually win. It seemed completely ridiculous. It still does. I am not a fan of the Good Guys Lose outcome.
6. Dream Fletch, Fletch
Jason: Admittedly, evidence of Dream Fletch’s actual skills are scant. He makes a nifty through-the-legs layup and bites a guy’s arm (legal in the ’80s), but that’s really it. My reasoning here is simple, though. The NBA salary cap for the 1984-85 season — the first season the cap was in effect — was $3.6 million. The Lakers had to figure out how to divvy that paltry (from a 2015 perspective) stack among the likes of Magic Johnson, James Worthy, Kareem, and a small forward phenom who we will call Dream Fletch. According to the legendary Chick Hearn in the above clip, the Lakers signed Dream Fletch to a contract worth $4 million a year. So, (1) the Lakers effectively made a mockery of the new salary structure, and (2) Dream Fletch was the highest-paid player in the league that season, nearly doubling Magic Johnson’s salary. The guy has to be very, very good.
Of course, highest paid doesn’t necessarily mean best. But listen to Kareem in the video. No hint of jealousy, no sign of discord. In fact, just the opposite. He praises Fletch’s rebounding and defense and says, “I don’t know where we’d be without him.” The 1984-85 Lakers would go on to win the title. Fletch, no doubt, played an integral role.
Shea: This is the best argument I’ve ever heard.
5. Scott Howard, Teen Wolf
Shea: I’ve always wondered this: Did Scott’s wolf basketball prowess improve his human basketball prowess?
Jason: Definitely. The other example of this is Jack Nicholson’s character in Wolf. Not only does he exhibit all the classic lycanthropic symptoms — sudden hairiness, spontaneous tooth growth, taste for raw flesh, territorial urination urges, heightened senses, off-the-charts sex drive and virility — but, at his day job as an editor at a publishing house, he suddenly finds himself capable of plowing through manuscripts at such a high rate that his boss asks him if he’s on drugs. Related: I would like to become a werewolf.
4. Jesus Shuttlesworth, He Got Game
Jason: I’ve seen He Got Game — along with The Wedding Singer, Titanic, Blade, and the sequel to Babe — roughly 500 times, because I worked in a movie theater for about five months in 1998. Because of that, it’s difficult for me to look at this movie in an unbiased way because of how much I associate it with my hating life and the smell of popcorn. This is a not-good, occasionally really bad movie with great basketball scenes that represents the beginning of the long descent from Denzel’s peak.
That said — Jesus Shuttlesworth, man. Separate yourself from the knowledge that Jesus is Ray Allen. And think of the movie’s interior logic. How good is Jesus Shuttlesworth? So good that the GOVERNOR of NEW YORK STATE has Jesus’s father sprung from Attica, WHERE HE IS SERVING TIME FOR KILLING JESUS’S MOTHER, in hopes that he can convince Jesus to attend Big State University, the governor’s alma mater. Read that shit again. I mean, I know that college recruiting is a dirty business, but that plan is straight-up insane. The plot reads like something out of Lee Atwater’s brainstorming journal.
Despite the aforementioned ridiculousness, He Got Game contains my all-time favorite pickup game scene: Jesus and friends balling out on a Coney Island hardtop, evoking Darcy Frey’s fantastic The Last Shot: City Streets, Basketball Dreams, to the strains of Aaron Copland’s seminal American classic “Hoe-Down.”
Some people, such as our boss, were not fond of Spike Lee’s music choices for He Got Game — the Copland choice in particular. I respectfully disagree. Copland is classic Americana. Spike is quite consciously making the statement that basketball and the inner city are as American as manifest destiny, cowboys on the prairie, and Annie Oakley. Plus, there’s the added meta-commentary of the song’s title, “Hoe-Down,” for anyone wondering why he didn’t go with something from the hip-hop oeuvre.
3. Shep, Above the Rim
Shea: Shep makes it all the way up to third on the list based on the strength of what has to be the greatest in-game performance of all.
In as high-stakes a setting as it gets (they were playing for a tournament championship, but really they were playing for life or death), Shep drops 38 points. He does this (a) by going 14-for-14, including 10-for-10 on 3s, (b) over a 2:34 stretch, (c) WHILE WEARING FUCKING CORDUROY PANTS. Who has ever done anything even close to that? That’s the best bit of basketball that’s ever been played. Have you ever even worn corduroy pants before? Jesus. I’m all of a sudden feeling very bad that Shep wasn’t closer to first place on this, Jason.
Jason: Maybe my favorite part in this whole movie is when Shep just straight-up knees Motaw in the nuts at half court and steals the ball. Not even trying to make it seem like a basketball play.
2. Brian, Thunderstruck
Jason: By far, my favorite thing about Thunderstruck, which is not a good movie, is how hard the script works to pretend that Russell Westbrook does not exist. For those who haven’t seen it, the premise of the movie is this: Brian, a 16-year-old Thunder fan, aspiring pro basketball player, fringe JV scrub, and team equipment manager, goes to a Thunder home game against the Detroit Pistons. During the game, Brian is selected to shoot one of those promotional half-court shots,1 which he misses badly, concussing the Thunder mascot. Durant2 takes pity on Brian and, nice guy that he is, assures him that he’ll make his next shot and gives him a signed basketball.
At the precise moment that both KD’s and Brian’s hands are on the basketball, Brian says, “I wish I had your talent,” which triggers an unspecified demonic hex, causing KD’s basketball abilities to transfer through the ball to Brian in a crackle of electrical energy. Durant then goes into a multi-game, 0-for-everything slump, while Brian tries out for and makes his varsity team. The lesson, as always: Ignore your fans, because they are vampires who will not be satisfied until they drain your very essence from you.
Now, you may be saying, “Isn’t this movie a rip-off of Like Mike? If Bow Wow attained the abilities of Michael Jordan via the same transitive law of basketball talent, how can the Thunderstruck kid be better? I mean, Bow Wow ended up playing in the NBA in Like Mike.”
First, shut up. Second, OK, fair question.
1. Like Mike came out in 2002, when Michael Jordan was 39 and in no way the best or even one of the 10 best players in the NBA.
2. Fuck Bow Wow.
3. How is it possible that Michael Jordan wears the same size shoe as Bow Wow? Why are MJ’s presumably childhood Nikes hanging from a power line in Los Angeles? I’m not even going to get into the make and style of the sneaker being anachronistic to the era in which Jordan was a boy. None of this makes sense. Magic energy flowing through a basketball is more plausible.
4. Kevin Durant is one of the best players in the league and averaged 28-8-5 in the season after the movie was released. If Brian has Kevin Durant’s powers in the movie (he does), and Kevin Durant is one of the very best players in the game today (true), and on his way to being an all-time great of the most rare kind (he is), then Brian is the greatest movie baller ever. Insert Latin phrase from debate class.
Shea: A big part of me feels like Russell Westbrook saw this movie and thought it was true. This would explain why he’s so pissed off all the time. He just seems like the kind of guy who starts sentences with, “I saw this movie one time … ” a lot. Also, and this is only semi-related, but if I could steal any NBA player’s talent, I’m going straight to Westbrook first. Nobody is more aggressively and actively athletic than Russell Westbrook right now.
1. Sidney Deane and Billy Hoyle, White Men Can’t Jump
Shea: Was there ever a question? What can I even say? They were the most compelling characters in the most compelling basketball movie with the most compelling arc during a completely compelling time period to be alive in America. And they knew how to play basketball. (One of my favorite side stories is that they had to teach Wesley how to play basketball for the movie and he was such a phenomenal athlete that he picked it up fully.) And they were cool. And they were the most fun.
Jason: The best movie ballers and the best basketball movie, period. So many great scenes, so many quotable lines. My favorite thing about WMCJ is how it toys with basketball’s racial stereotypes without ever being beholden to them.
Billy is the street-level skell with the gambling problem. Sidney is an upwardly mobile professional who has the roofing thing and the cable thing and the basketball thing.
It also brought the “your mama” joke idiom to the mainstream.3 Fun fact: Keanu Reeves was almost Billy and would have gotten the role if he’d had any basketball ability whatsoever. Man, can you imagine?
It’s impossible not to think of these guys as a pair. The tough question isn’t who is the greatest fictional basketball player, it’s who is better: Billy or Sidney?
I think it’s Billy. He beats Sidney in the initial shooting contest, hits the hook shot for the Sudan, and almost wins the game when Sidney double-crosses him.
Shea: Billy. Billy’s better. Billy’s better for all the reasons Jason mentioned and also because by the end of the movie he’s able to dunk. His only real weakness was that he was a bit volatile whenever someone would call him out for being white or unathletic. When he dunked, it was like how Tony Parker became THAT DUDE after he won the 2007 Finals MVP. Before then, he’d always been very good but also kind of a question mark (if you’ll recall, Popovich sat him down in Game 6 of the 2003 Finals in favor of Speedy Claxton). After he won the Finals MVP, he was a goddamn basketball mega-hawk.