The video above is the 30 for 30 film on Sonny Vaccaro, a famous and infamous character in the sneaker world who is celebrated and vilified and revered and maligned. It’s about what his role was (or maybe wasn’t) in turning basketball shoes into a multibillion-dollar industry. Sole Man is interesting even if you are not into basketball or shoes, because really it’s about how powerful people interact, which is always intriguing. I wanted to write about it, but I wasn’t sure how because while I do have feet, I’ve only ever cared about what I put on them three times:

• When I got my first pair of Nikes. That was the fifth grade, and was the first time I’d ever given any thought to what I was wearing. Really, I didn’t even know I wanted them. My mom just showed up one day with them. I remember being very excited about it because where I was from, having Nikes meant that you weren’t poor (that sort of thinking, incidentally, is an easy tell that you are, in fact, poor — or rich). They were a full size too big. I wore a lot of socks that year.

• When my mom brought home Rollerblades. The problem here was that they weren’t actually Rollerblades, they were just big-as-fuck shoes that looked like Rollerblades without wheels. I swear they came all the way up to the middle of my calf. My mom had bought them in the summer between my sixth- and seventh-grade years. They were supposed to be my play shoes because I’d outgrown my school pair and wasn’t going to get new nice ones until the next school year. I put the Rollerblades in the closet and never ever EVER wore them. I stayed in those too-small shoes. I didn’t wear a lot of socks that summer.

• When my mom bought me the Reggie Millers. They were the first signature athlete shoes I owned, because Reggie Miller was the first basketball player I ever loved. I loved Reggie Miller so much. He was skinny and had big ears and weird teeth just like me. He also never shut up, a trait I have always appreciated.

Those are the only three times I remember feeling anything about my feet beyond “I hope I don’t get glass in them,” so rather than just write about shoes, I talked to some people who know a lot about that sort of thing. One is Jake Woolf, a very handsome style writer at GQ who owns many jackets and shoes. The other is Lawrence Schlossman, the very handsome editor-in-chief of Four Pins, Complex’s menswear site (he’s also the host of Complex TV’s Fashion Bros. and cowrote that big Fuck Yeah Menswear book).

OK, let’s start easy, with a topic that I wish more people talked about. Allen Iverson’s first shoe, The Question: That’s the coolest basketball shoe that’s ever been made, right?

Lawrence Schlossman: It’s unquestionably up there, but coolest of all time might be a stretch. It’s a great shoe to actually ball in — or so I hear; I’m Jewish, so I don’t play any sports — but hard to wear casually. It’s easily the coolest signature athlete sneaker Reebok has ever made, though, for sure.

More Grantland Q&As Click here for all of our interviews with fascinating people from the worlds of sports and pop culture. Jake Woolf: Those were actually the first sneakers I ever begged my parents to buy me, because I’m too young to have begged for Jordans. Those and the T-Macs were my Jordans. AI made them easily the coolest sneaker of the early 2000s, but now that I’m older it’s pretty hard to argue against any Air Jordan from 1 to 13, except for the 9s. 9s are garbage water.

Schlossman: Yeah, Jordans will always be king, but for that one fateful night when AI crossed up the greatest basketball player ever, The Questions held the title belt.

Has Steph Curry somehow made Under Armour shoes cool? If so, he needs to win, like, probably the next 20 MVPs.

Schlossman: For my money, Under Armour shoes are super wack. All that next-level performance stuff they lace the best point guard alive with (R.I.P. CP3’s life) doesn’t mean shit when they look like they were designed by a third-grader. Granted, as Steph’s star continues to rise, we can probably expect an increase in UA’s market share … but I’ve never once seen anyone wearing ’em on the street, and I doubt I ever will.

I feel silly when I say or write the phrase “sneaker culture.” Is that because it’s actually silly or because I am ignorant?

Schlossman: Both? Sneaker culture as it exists today is basically an embarrassing, greedy, clusterfuck bizarro-world version of what it once was, so on that note it should be shamed. However, there are still members of the old guard who look at sneakers with the kind of love and admiration a normal person might with their children, though they can be corny in their own right, admonishing an entire new generation of thirsty flippers sight unseen. The best analogy I have for sneaker culture is hip-hop fans. It’s a constant struggle between “old heads” and new, younger aficionados jockeying for a voice in a popular and crowded arena.

Woolf: I think it’s kind of a fallacy that may or may not have been invented by Nike to sell more sneakers. Like, I guess kids have fun Instagramming their kicks, selling kicks, going to conventions, and doing drugs while waiting in line to buy sneakers, but does that constitute a “culture”? I don’t know. But the most important thing is that, yeah, saying “sneaker culture” just feels incredibly nerdy to say. It’s like when struggle rappers say they’re starting a “movement” or making songs for “the culture,” when really they mean that they just have no friends.

More important moment to sneaker culture: Dr. J winning the 1976 ABA slam dunk contest, Jordan winning the 1988 NBA slam dunk contest, or Dee Brown pumping his shoes up before his blind dunk in 1991?

Schlossman: Relevancy in the sneaker world always goes through MJ. That’s just a fact. OK, I will acquiesce to the pump being right up there with the best shit Reebok has ever done, and Dee Brown so blatantly juicing his kicks up is an incredible moment in flexing history, but, again, everything sneakers goes through His Airness first and foremost.

Woolf: I think what we’re getting at is that in the wake of the Air Jordan phenomenon, every sneaker company tried and ultimately failed to create a signature sneaker at that level. For one, no one is or will ever be Michael Jordan. But also these other brands like Adidas and Reebok just didn’t have the design talent or advertising savvy that Nike and Wieden+Kennedy did. They were all just making signature sneakers because they felt like they had to. Even to this day, Nike is trying its best to make hot signature shoes with Durant, Kyrie, and even Kobe (which has been moderately successful, relatively speaking), but no one else has that MJ juice.

Fair enough. Let me use that same premise but make the question less obvious. Arrange these moments in order of importance to sneaker culture:

• Run-D.M.C. doing “My Adidas”

• The “you stepped on my brand-new white Air Jordans” scene from Do the Right Thing

• Fat Joe licking the sole of his shoes on MTV Cribs

• Back to the Future Part II’s Air Marty McFlys

Schlossman: First is Run-D.M.C. doing “My Adidas.” An iconic sneaker becomes even more iconic thanks to an iconic cosign. Sales were BOOMIN’. Also, Adidas is pushing the Superstar incredibly hard in 2015 after finding similar success relaunching the equally classic Stan Smith last year.

Second is the “you stepped on my shoe” scene from Do The Right Thing. Without getting wildly out of pocket, this kinda serves as an allegory for race relations in America today that’s more pertinent and urgent than ever, so its impact as a moment when cinema transcends the screen cannot be understated.

Third is Fat Joe licking the sole of his shoes on MTV Cribs, the most incredible moment in Cribs history outside of Redman showing off his stash box and Dave Chappelle ethering the entire show’s existence with one of his best skits ever. Honestly, you’re not living until you’ve literally tasted the spoils of victory by licking a brand-new fire sneaker you just copped.

Woolf: An incredible moment for MTV, Fat Joe, and wealthy people everywhere, but not really important to sneakers. But let’s be real — Fat Joe will lick just about anything.

I wish we all got to see Fat Joe lick more things.

Schlossman: Fourth is Back to the Future Part II’s Air Marty McFlys. This was cool at the time but has since become this quasi-trash moment in retrospect since it led to Nike releasing the Air Mag, their corniest, most ridiculously gauche, overhyped sneaker to date. Those shits didn’t even lace themselves!

Woolf: Back to the Future Part II is second place for me. They were actually science fiction and Nikes at the same time, which is basically the perfect formula for appealing to teenage boys. It’s also awesome that they were designed by Tinker Hatfield, the guy who designed the Air Max and all of the best Air Jordans. Because the movie took place in 2015, Nike is releasing them later this year in full self-lacing form, and people are going to definitely punch each other in the face to get a pair. For the record, though, they’re insanely ugly and anyone who’s worn a pair from the limited-release auction back in 2011 has looked like nothing short of a hypebeast clown.

Wait. Let me jump back a bit, because I just thought of this. Has there ever been a bigger fall-off in shoe design than going from Iverson’s The Question shoe to Iverson’s The Answer shoe? Because, dudes, what a mess. And to expand on that, or maybe to counterbalance against it, I have to make sure I mention the commercial for The Answer. Do you remember that? It was the one where Iverson explained how to do his crossover. Great commercial, awful shoe.

Woolf: The O.G. Answers, yeah, those were terribly ugly. Though I can’t in good conscience hate on them because as a naive kid I thought Reebok’s DMX technology had something to do with rapper DMX, which was actually reasonable when you consider the timing of all of this (1998-2000).

I was very sad when I found out that that was not the case.

Woolf: Also, Iverson was wearing the Answer IVs when he did this:

https://www.youtube.com/watch?v=H273e0Gk0zQ

Schlossman: Not that I needed any more convincing at the time to be all in on AI, easily my favorite player growing up, but that crossovers-for-dummies commercial definitely sold me heavy even though it will never be as good as this iconic Nike joint:

Not to mention that seemingly worthless DMX technology — which I still don’t understand, by the way — had me gassed more than any sneaker selling point outside of maybe, like, British Knights selling springs in their shoes that supposedly would make you be able to dunk even if you were a 9-year-old white kid from the suburbs. I remember trying to tell my parents the DMX technology made these shoes a steal, like an adult would even give a single fuck about sneakers. They still refused to buy them for me. Looking back, The Answers were pretty butt, but when they dropped I wanted them more than anything.

Who are the white basketball players with shoe deals? Where are they? Why doesn’t Kirk Hinrich have a shoe deal in place?

Woolf: I think Kyle Korver had a deal with Converse but now he wears Nike, which owns Converse. I think we just live in a time when the most electrifying and marketable players in the league happen to be black. That said, a few white guys have signature sneakers, albeit with smaller brands. Kevin Love has a deal with a Chinese sneaker company called 361 Degrees. Chandler Parsons is with a company called Anta, but he wore Jordans on the court a while ago. Steve Nash used to have a signature sneaker with Nike, but it doesn’t exist anymore and no one liked that sneaker anyway. And that’s when he was MVP.

It feels a lot like you’re saying Mason Plumlee isn’t exciting, Jake.

Woolf: The Mason Plumlee signature shoe would basically just be one of those Cole Haan Lunargrand desert boots. Here’s Kevin Love’s signature shoe.

Oh my word. It’s like a car accident. It’s like if someone took all their bad ideas and put them on your feet. OK, let’s do a quick game. I’ll name some basketball players, and you guys give them shoes. They can be real actual shoes or, like, if I say Zach Randolph, you can say his shoes should be we just dip his feet in concrete and he goes out and runs around like that. Let’s start with Amar’e.

Woolf: Amar’e gets Nike X Riccardo Tisci boots because maybe they’ll be supportive enough for his old-ass knees.

This got personal real quick. Jeremy Lin?

Woolf: Nike Air Yeezy 2. Really hyped a few years ago, now just seem corny when you see them in person.

Zach Randolph?

Schlossman: Z-Bo is a beast and a generally frightening human. Assuming how firmly he is about that life and the fact that Stephen Jackson all but confirmed our suspicions on The Grantland Basketball Hour, I’m gonna go ahead and recommend Z-Bo strap on a pair of Vietnam-issue jungle boots and get back to murdering people in the paint.

Mario Chalmers?

Schlossman: A pair of gray geriatric New Balances would be rad because is that not the funniest mental image? Chalmers just running the point in the corniest dad shoes imaginable.

Tiago Splitter?

Schlossman: Tiago being Brazilian and all just seems like he’s a super chill bro, so his career moving forward would probably flourish as a specialist in Rainbow Sandals.

Popovich?

Schlossman: Wait, can Chalmers give Pop his New Balances?

Woolf: New Derrick Rose signature sneakers?

Jake.

Woolf: Also out of left field, but it’s pretty amazing that Rasheed Wallace wore Air Force 1s exclusively throughout his career.

Is that true?

Woolf: I’m not sure if he ONLY wore Air Force 1s, but he definitely wore them most of the time with the strap hanging off the back, because ankle support is overrated.