Why You Don't Know the Name of the Biggest Star in NBA Media

Meet Jxmy Highroller, who's worldwide but not on Twitter

I was at a dinner, hosted by a friend who invited other friends. People discussed their jobs, and mine came up, organically I promise. An attendee named Jonathan asked, “Do you know Jimmy Highroller?”

“Jimmy who?” I responded, thinking the name must have been mispronounced or garbled. After over a decade in NBA media, I’d at least heard of everyone in that orbit, if I didn’t directly know them. Or so I figured.

“Jimmy Highroller,” he said. “He makes NBA videos on YouTube. I watch them all the time.” 

Had I really been on Substack so long as to not recognize a major NBA content creator? I texted about a dozen former colleagues, “Do you know who Jimmy Highroller is?” The answer, without exception, was, “No.” 

My confusion only grew after I got home and looked up Jimmy Highroller (Spelled “JxmyHighroller”). It turned out he had an astounding two million subscribers. Some of his videos boasted eight-figure view totals. 

A week later, I’m at the same house, talking to a different friend, who happened to be a weekend warrior sort of pickup basketball player. So I asked, “Who is Jimmy Highroller?” Of course he knew Jimmy. As did the college buddy of mine I hung out with the next day.

Based on objective standards and my own subjective non journo social circle canvassing, Jimmy Highroller is a giant in my industry, one of the most popular men in NBA media, if not the most popular. ESPN would kill for videos that rack up his numbers. When you compare Jimmy against ESPN over a span of the last two years, Highroller has produced three videos that would rank as ESPN’s most watched. And Jimmy doesn’t have the entire Disney apparatus pushing his content. He appears to be crushing Goliath as a singular force.

Yet, I and probably more than 95% of my former colleagues in NBA media had never heard of the guy. How could this be? How could involvement in NBA media be almost inversely correlated with one’s knowledge of a top producer in it? And, just who the hell was Jimmy Highroller? Did he even exist? Was he a man or a myth?

Jimmy Highroller’s real name is Grayson Anderson. He lives in the state of Washington, in “a moderately sized city” as he terms it. He has a wife he met in high school, and two kids. After college, he worked a few months as a car salesman, but didn’t feel the job was right for him. Then his YouTube hobby took off when he started listing high school basketball stars to an instrumental. 

The JxmyHighroller channel has since generated millions of dollars in revenue. You’d think Mr. Anderson would have used its success as a way to get famous, but he’s mostly stayed out of frame. Anderson used to do the occasional camera-facing Q&A on his channel, but has since stuck to video narrations. When we spoke, he told me it was the only interview he’d ever conducted with an outlet, outside of a podcast he did with a friend as a one-off. 

“I think it’s just kind of who I am,” he explained of his fame avoidance. “End of the day, I don’t really feel like I’m important; I feel like I’m good at what I do.”

And Twitter? He doesn’t bother with it. Anderson explained:

I wouldn’t have a Twitter if I wasn’t a YouTuber, so why have one now? It’s a really toxic environment and it seems nothing ever good comes of it.

He continued:

I provide people with entertainment. I give guys a break from everyday life, let them kick back for 10 minutes at a time, and hear a story. And that’s just about it. I’m not an influencer. I’m not here to change anybody’s life, make them somebody they’re not. I’m just here to entertain some people.

I’m not sure we have archetypes or stereotypes of what a YouTube celebrity is supposed to be like. I recall that when top YouTuber Mr. Beast appeared on Joe Rogan’s podcast, many were struck by how nice and personable 23-year-old Jimmy Donaldson came across. Perhaps there’s a widespread assumption, often unsaid, that a YouTube creator must be some sort of weirdo. I mean, what sort of normal person would successfully hack this nexus of psychology and algorithmic rhythms? You’d figure it’s a psychopath who sees the human mind as easily manipulated gears and levers. Or at least I’d figure. Yet Donaldson, though his work methods were extreme, appeared less narcissistic than the average celebrity. He seemed like a down-to-earth guy and a solid hang.

Grayson Anderson comes across similarly, even if he perhaps had more reason to think highly of himself earlier in life. “When I was younger I was more boisterous,” Anderson said. “When you’re good at sports and you make friends, you feel like you’re the guy.” Before he was Jimmy Highroller, Anderson was a high school track and basketball star. He attended Washington State University on a track scholarship, where he excelled as a high jumper between injuries. Anderson explained all this in a video titled, “My D1 Story,” which was his rare foray into self-expository. That video has since been pulled, due to musical copyright issues. You can, however, watch a video of a British guy reacting to Anderson’s original video. 

The British guy is performatively shocked by Anderson’s athletic feats, especially when Grayson’s high school basketball coach appraises him as “the most freak of an athlete I’ve ever seen at the high school level” as a highlight montage of Anderson plays. The high school coach adds, “Not a game went by, and I’m not joking, not one game went by that, not a ref and an opposing coach said, ‘Who is that kid?’” 

On its face, it’s not surprising that a super-athlete found success by describing the exploits of athletes. But here’s the unexpected aspect and perhaps why the Brit is shocked: Almost none of Anderson’s athletic background appears to inform his famous videos. He’s not breaking down the game from the perspective of a player. Indeed, his videos, which often obsess over the historical significance of statistics, using charts and graphs, seem like they could have come from the least athletic of basement-bound Internet sleuths. As in, the weaponized autism meme could apply to such productions. The man behind Jxmy is an affably popular jock who produces the sort of granular observation usually reserved for antisocial nerds. And he does it all so well.

If you want an example of a classic JxmyHighroller video, look no further than “When A 17 Year Old Luka Doncic Had To Guard MVP Westbrook,” attracter of 5,386,552 views as of this writing.

It’s a fairly unassuming title, and it describes an event that wasn’t significant enough to be well-remembered. In 2016, Real Madrid played Oklahoma City in an exhibition game and young Luka Dončić was overmatched against Westbrook, who was kicking off an eventual MVP campaign. 

Teen Luka sucked against prime Westbrook. Fair enough. But then the video starts progressing through time. We see Dallas Mavericks Dončić dominating Westbrook and his teams. There’s something jarring to the visual of how the dynamic flips. Then JxmyHighroller’s video starts skipping around the basketball world, to these snapshots of NBA stars sharing scenes with kids who’d later become famous. Andre Iguodala bullies a 16-year-old Devin Booker in a game of 21, only to later bear the brunt of Phoenix Suns star Devin Booker’s scoring barrage. Childhood Trae Young lends the best visuals to the video, because he appears so tiny as a kid when taking photos with NBA players he’d later torch as a pro. 

And yes, it all makes sense. The young grow up, gain strength, learn, and challenge the established order. But there’s a magic in actually seeing the comparison points. ESPN, with its daily debate shows, is all about the present moment and less about how we got here. There’s no time for that as you’re quick-cutting from segment to segment. They’re always selling you a present so stimulating as to make the past irrelevant. JxmyHighroller reminds you that the NBA is actually one big story, in a constant conversation with itself. Of course, nothing can matter unless the past does too. 

Jonathan, the guy who tipped me to Jimmy Highroller, was something of a history podcast fan. He loved Dan Carlin’s pod, as do I. And while I wouldn’t have figured that an affection for “Ghosts of the Ostfront” would have much in common with a affinity for deep dives on the Ball brothers, so it does. History is history, on the floor or on the battlefield. And a lot of dudes love a journey to the past, wherever it leads.

“A couple years ago I started shifting to more history-based stuff,” Anderson said. “Some of my favorite videos are, a story of a guy trash talking MJ.” He explained his process, at least the one that precedes his Final Cut Pro and WavePad edits:

I’ll be surfing on YouTube and then I’ll see a clip and go down the rabbit hole. What are the numbers involved? Oh, here’s a weird factoid. You just go down the rabbit hole and suddenly you have 15 minutes of content. Then you’re saying, “Yo, I should make a video about this.”

Often, it’s not enough to just find what’s historically intriguing. Increasingly, for Anderson, the game is to tether a present event to the not-so-distant past.

Take right now, it’s the NBA playoffs. That’s where everybody’s eyes are right now. I like doing the history stuff, but also making it current. Like right now I’m doing a video on Kevin Durant and his first-round series and how it was a complete meltdown. I took the currentness of it, and compared it against the history, and investigated whether … was it the biggest meltdown?

That concept sounds simple enough, but the video journey takes you to unexpected places, both foreign and familiar. The examples cited are reminders of the long-forgotten and indelibly memorable, all merged into one accessible narrative. The view count on the latest KD video is climbing, on its way to one million views at the time of this writing.

Now, notice something about that video, specifically the thumbnail still shot you see before you click. Look at that photo of Kevin Durant sitting with a young Jayson Tatum. See how the image quality is quite shoddy. Odd, right?

This aspect is intentional. There’s a reason you’re seeing a poor-quality image, though nobody quite knows why to a definitive degree. I just know that its presence is all part of a collaborative, ongoing trial-and-error process.

As a star YouTuber, Grayson Anderson is in conversation with other star YouTubers. You might assume that such creators are wholly atomized in their respective Internet kingdoms, but theirs is actually a highly social community. They’re all working together, informally but obsessively, trying to figure out what succeeds on YouTube. In this Joe Rogan clip, you can see how Mr. Beast built his career up in this way, through teamwork among friends, in a process they called “Masterminds.”

Mr. Beast, who boasts a video that’s reached an astounding 247 million views, and who runs channels that translate his productions into multiple languages around the world (his reach grows by the day in Brazil and Mexico), might be the most famous entertainer on earth by objective measure. Such is the compartmentalized nature of YouTube that this can be so simultaneous with the decent chance you’ve never heard of him and the excellent chance that your mom hasn’t either. So how did Mr. Beast achieve this new sort of international renown? He explained a foundational education that sounds like something between film school and card counting. Of his initial YouTube friends, he said:

We basically talked every day for 1,000 days in a row and did nothing but hyperstudy what makes a good video, what makes a good thumbnail, how to go viral. 

This was a granular process.

We’d do things like, take 1,000 thumbnails and see if there was any correlation between brightness of the thumbnail to how many views that it got. Or like, videos that get over 10 million views, how often do they cut the camera angles?

Within a month, the Masterminds crew members went from earning 10K-20K views to reaching over a million. It all made sense to Mr. Beast, who explained:

You mess up, you learn from your mistake. You in two years might have learned from 20 mistakes. Or if you have four other people who are also messing up and if they learn from their mistake, they teach you what they learned. Hypothetically, five years down the road, you’ve learned five times the amount of stuff. So it helps you grow exponentially way quicker. 

This method of collective study works, and so it’s breeding a spirit of collaboration among creators you might assume would viciously compete for attention. Anderson cannot reveal exactly what he’s picked up from whom, but he’s in conversations and he’s always learning. He relays how the conversations go, saying,

It’s tips like, when there’s an arrow and it’s 200 pixels wide in the thumbnail, I get this many views. They do all of that stuff and they gather data from thousands of videos and they’ll just find these correlations. The title has to have “never” in it. And Michael Jordan is in the thumbnail. That sort of thing.

So why is the pixelation shoddy on Anderson’s last video? That’s what’s been working of late:

Last year, I’ve been taking these really raw, 360p screenshots of games and moments. I used to use more refined shots, a really high-definition picture. But recently I’ve been taking these screenshots. That seems to pique people’s interest.

The fuzzy images work better than the crisp images. Nobody can be completely sure why, though Anderson has his theories:

When something seems too curated, too refined, it seems too commercialized. There’s this saying that it’s always the low-quality videos that are best. In my opinion, when you’re with your phone out, it’s completely candid and you catch something amazing, you’re not going to have the perfect angle with the perfect lighting. If it’s too crisp, I think it really deters people. Because people have had too many experiences of clicking on a crisp thumbnail and it being disappointing. 

Anderson prefers a more naturalistic approach than some others. Apparently he’s the unusual sort who makes the video before he makes the title and thumbnail:

All the big creators I know, they almost work backwards from what I do. They come up with the title and the thumbnail first. Because if you can’t get people to click on it, it doesn’t matter. 

So, in a way, Grayson Anderson is a pure artist, expressing himself through his own interests. He’s not selecting the thumbnail first. But in another way, he’s hacking your interest, in a semi-corporate application of data science. He’s making the thumbnail blurry.

As he relayed his process for the first minute of videos, it started to dawn on me that we shared similarities. The realization came from what Anderson said about using mystery to provide a hook:

Is my hook good enough? These days, getting people to stick around for 15 minutes is really hard to do. In the first minute, how many people can I convert? So maybe I propose something. Something that seems almost too good to be true. 

Well shit, my articles typically take about 15 minutes to read, and yes, I worry about whether the first few sentences hook you. I hoped that the dinner story with Jonathan didn’t lose your interest, and counted on its inherent mystery to pull you forward. I asked a few questions before the paywall divider because I’d once seen a charismatic preacher use that trick to set up a sermon that I stuck around to hear. Am I thinking algorithmically? Am I just a less efficient version of what I’m describing?

This brings us to a certain convergence, either an immense coincidence or a predictable overlap, depending on your perspective. In researching this article, I, of course, looked up what the most viewed Jimmy Highroller video is. It’s “How Nike Lost Stephen Curry with ONE WORD,” a title that compelled me for reasons other than its ONE WORD tease.

This is because the Highroller video is a recapitulation of an article I wrote in early 2016, to date the most widely read thing I’ve ever written and not by a little. According to Chartbeat, that post on Nike fumbling Steph Curry to Under Armour was the 39th-most read English-language story of 2016, a year that featured some stiff competition in politics, if I do say so myself. It was an unexpected outcome for an article that ESPN The Magazine had cut from its print issue, assuming there wouldn’t be much of an audience.

Highroller’s version came out on November 7, 2017, well over a year later. That lag did not hurt the video’s popularity, obviously. At the time of this writing, his video has racked up more than 14.7 million views — more eyeballs than I likely drew in print.

To be clear, I take no issue with Grayson using my article. I lost nothing from the exchange. I’m mostly just amazed that it exists in some other form, consumed by the population of a midsized nation, and that it all happened without my knowledge.

What sold my article was the reporting within, reporting I’d gotten extremely lucky on. Upon getting those details, I felt this responsibility to craft the information for maximum exposure. Edits were made to the hook that burn me up to this day, even if the story worked and I should let it go. You get only one chance to do a story like that. Or so I thought.

I asked Grayson, “What worked about the video version? Why did this pop for you?” He laughed. The Steph Curry Nike video had just come up in one of those creator discussion sessions, brought up immediately by a legend in the field:

The first thing he mentioned to me was that video. He said, “According to our algorithm, that’s the perfect thumbnail and title.”

Grayson had finally nailed the systematized approach with this one, earning buy in with an efficiency the greatest ad men could only dream of. He laughed a bit about stumbling into this perfection, before adding, with perhaps a note of reassurance.

That being said, there still has to be a story there.