For a long time, March Madness was a great excuse for magazines and websites to make their own pop culture–related brackets to, say, pick the best TV season ever, the best skit from Chappelle’s Show, or the best fast food restaurant. This year, though, bracket-making became a recreational activity for Twitter users. It started when Twitter user Carrington Harrison went viral with a 64-song bracket he made of Kanye West’s best work (as of this writing, Harrison’s tweet has over 30,000 retweets). From there, people started making brackets for their favorite artists—Future, Young Thug, Nicki Minaj, Dave Matthews [extremely Dave Matthews voice: I DID IT]—and then the trend spilled beyond music and into things like millennial kids’ shows, teen movies, and Pixar movies. Twitter has been so flooded with brackets that four days ago, Vox galaxy-brained and made a bracket about all the brackets.

But in the sea of pop culture brackets, something was noticeably missing. Obviously I’m talking about how no one made a bracket covering all of the baseball caps worn by Leonardo DiCaprio.

Oh—this wasn’t obvious to you at all? This is a topic only I have been keeping tabs on? Well let me catch you up, then: Leonardo DiCaprio, Academy Award winner, noted boyfriend to a parade of models, loves to wear baseball caps. And I mean LOVES. The guy must own stock in Lids or something. In about 90 percent of paparazzi photos of Leo, he is wearing a baseball cap. (In the other 10 percent, he is wearing a newsboy cap.) It is often pulled down to his eyebrows, to obscure his identity, and its brim is often bent awkwardly, as if Leo folded it in haste for some reason. The wildest thing is that he wears so many different baseball caps—over the years he’s supported colleges like Colorado State, Rice, and the University of Rhode Island—and has zero team loyalty. Here he is at the 2015 U.S. Open wearing a Notre Dame cap (and vaping):

And here he is in 2009 wearing a Michigan cap:

Here he is in Italy in 2011 wearing an Alabama cap:

And here he is in 2016 wearing an Auburn cap:

Notre Dame and Michigan hate each other! Alabama and Auburn hate each other even more! Leonardo DiCaprio must be the only person on the planet to have worn all four of these caps at one point in his life.

So of course we need a bracket to discuss the best baseball cap Leo has ever worn, and because March Madness season came and went without anyone assembling this important bracket, I have made one myself:

So many hats. (Please know that it was not very hard to make a 64-team bracket of Leo’s baseball caps; cuts actually had to be made.)

I separated the hats to the best of my ability into four regions based on the locations of the hats’ teams. I then seeded the hats in each region based solely on how random their appearance on Leo’s head felt. For example, the Florida Atlantic University cap got the 1-seed in the South, while a University of Miami cap got the 16-seed. Also, seeding was occasionally rigged so that hats of the same team were forced to face each other in the first round.

The best way to fill out this bracket and accomplish the goal of figuring out Leo’s best baseball cap is to go region by region. Starting with the East, I’ll show you my picks and then break them down. Though seeding was based on randomness, going forward the matchups will be determined by more than that, also taking into consideration the quality of the hat, the iconicness of the hat, and the activities performed while wearing the hat. OK, let’s get to the hats.

The East Region

Four Stray Observations

1. Though we can’t read too much into Leo’s hat choices—they’re so random and extensive that trying to derive any meaning from them is a fool’s errand—it does appear that he is a bigger Mets fan than Yankees fan. I think it’s mostly because the Mets are more adventurous with their color palette, and therefore have more hat options. Leo is a volume guy when it comes to hats, so the more options, the better.

2. It is really hilarious that during his mountain-man phase—when he was shooting The Revenant—Leonardo DiCaprio decided to wear a West Virginia Mountaineers hat:

That is just serious dedication to making your baseball cap fit your circumstances.

3. This region is filled some incredibly weird hat choices. There’s the A.S. Roma hat (no. 3 seed, and the only soccer hat in this tournament) that Leo wore at a 2001 Lakers game, the NRDC hat (no. 13 seed), the mega NRDC hat (no. 1 seed) that depicts the planet Earth literally on fire, and the camouflage Montauk hat (no. 12 seed), because nothing says “Montauk” like camouflage.

A fun fact is that most of these random hats are connected to Leo’s former girlfriend and Tom Brady’s current wife, Gisele Bündchen. Gisele wore the same A.S. Roma hat when she and Leo attended Game 4 of the 2004 NBA Western Conference finals (they sat next to Mark Wahlberg, who wore a Titleist hat). The mega NRDC hat also pops up in this classic photo of Leo kissing Gisele on the face at a 2003 Lakers game (I think Leo took Gisele to more basketball games than any other girlfriend):

The camo Montauk hat has no connections to Gisele—Montauk is just a place Leo likes to go to listen to Nancy Atlas, sip rosé, and make out with Kelly Rohrbach.

4. The full image of Leo in a St. John’s University hat needs to be seen, because it is basically a still from Molly’s Game.

Most Intriguing Matchup

The 1-seed vs. 16-seed matchup between two non-sports hats, the NRDC Burning Globe hat and the Adidas hat Leo wore while eating spaghetti in the ’90s:

The latter is such a great hat, and nothing is more “goals” than Young Leo eating a giant bowl of pasta alone. These photos also inspired a legendary Photoshop that substituted Leo’s glass of ginger ale for a pouch of Capri Sun, and it’s a bonus that the Adidas hat was part of that marvelous creation.

But that hat couldn’t unseat the Burning Globe hat, with its extremely literal interpretation of a complex topic, its aforementioned connection to Gisele, and the fact it predicts the future. No one should be surprised that Leo has become a staunch environmental activist—because the guy was wearing a picture of the Earth on fire in 2003.

Why This Hat Won

The East Region final between Leo’s 2001 Puma hat (no. 14 seed) and his 2015 classic blue Mets hat (no. 8 seed) was really tough to decide. How can you pick against this image:

There is so much to like here. First of all, the Gangs of New York hair, the sunglasses, and those nerdy sneakers and white tube socks—WHAT A LOOK. Second of all, Leo and Gisele are using a shopping cart for … maybe four bags of groceries? Third of all, this image of a woman being draped over Leo while he mindlessly goes about his own business is a recurring one throughout his career. Here he is with model Toni Garrn in 2014; and here he is just last week with model (and “step-daughter” of Al Pacino) Camila Morrone.

But the blue Mets hat is nearly undefeatable, for it was the chosen hat for Leo’s romp around New York City in 2016. It is the hat that was worn when he rode around Manhattan on a Citi Bike, and it is the hat that was worn when he, as the Daily Mail so eloquently put it, took a “vape break.”

Just phenomenal. The reigning Best Actor at the Oscars (at the time), leaning against a tree in Hudson River Park, pulling up his shirt so that you can see his boxers, and ripping mad vapes. One of the most iconic moments in Leo’s hat history.

The South Region

Four Stray Observations

1. Let’s just briefly talk about the Anaheim Ducks cap (no. 10 seed) Leo wore in 2010. The first thing worth discussing is that he wore this hat not at a Ducks game, but at a Lakers game. The second thing is that while it does make some sense that Leo would own an Anaheim Ducks hat (because the Ducks are an L.A.-adjacent team), it makes less sense than wearing a Los Angeles Kings hat. To my knowledge, Leo has never worn a Kings hat—apparently he leaves that job to his friend and fellow Posse member, Lukas Haas. The third thing is that this hat looks like a bootleg that was not sanctioned by the Ducks or the NHL. “ANA” in block letters and that’s it??? It’s eight years later, but the Ducks do not currently sell any hats that simply say “ANA” on a blank background, and I bet they never did. It’s weird enough that Leo wore an Anaheim Ducks hat—it’s much weirder that it seems like he bought the hat on Canal Street.

2. In 2017, College Choice ranked Florida Atlantic University as the 29th best college in Florida. But of course Leo owns one of its hats (no. 1 seed).

3. VCU’s Cinderella-story run to the Final Four happened in 2011, but Leo was spotted wearing a VCU cap (no. 3 seed) two years before that. This guy is either extremely on his stuff or he just goes into Lids, closes his eyes, spins around four times, points at a hat, and that’s the one he buys that day. My guess? Leo saw VCU upset Duke in the 2007 NCAA tournament and was like, “Yoooo, that’s dope. I need one of their hats.”

4. Anytime someone tells you their crush is Leonardo DiCaprio, just show them the Atlanta Braves photo:

Most Intriguing Matchup

The South final features two great moments in Leography. You have the 2-seed Rice, which is a 2-seed because why in the world would anyone ever own a Rice hat? Said noted Houston resident Michael Baumann: “I’d never thought about it but the only people I’ve seen wearing Rice hats are Rice baseball players.” It’s also great that Leo wore the Rice hat at a 2011 Lakers game he went to with Tom Hardy. Hardy wore a cooler hat; a retro dad hat for a team from the Negro Leagues; and also a hat that wasn’t a Rice hat.

And then you’ve got the 4-seed Auburn hat, one of the few hats Leo has worn multiple times. I’m not sure anyone from outside the state of Alabama has ever worn an Auburn hat—just another instance of Leo really pushing the sartorial bar. But that’s not why Auburn ultimately won the matchup ...

Why This Hat Won

Auburn won the matchup because the hat was the uniform for two important moments. First, there was the time he practiced riding a bike … while on a bike in August 2013.

“So how do you do it again? I know you put your arms like this, but after that I’m lost.”

But more importantly, Leo was wearing the Auburn hat when he and then-girlfriend Nina Agdal were rear-ended in the Hamptons in 2016. The hat was in full view while Leo was consoling Nina–generally laughing at her tears.

“The only reason he survived was because he had his Auburn hat on,” a commenter on a Rivals.com forum said. “Allegedly the car flipped 14 times and blew up twice but Leo and his hot girlfriend walked away injury free due to the hat shielding them from the massive destruction caused by the multi-car incident.” All of that is completely false—what I’m presupposing is, what if it wasn’t?

The West Region

Four Stray Observations

1. You may notice that there are a bunch of Lakers hats in this region—finally, a hat that makes sense! Of course he’d wear Lakers hats to Lakers games. What’s funny, though, is that Leo’s choice of Lakers hats is terrible. They’re all hideous: black and poorly designed. The 1-seed Lakers hat has the team’s normal logo—that’s good—but purple on black is never great. Then there’s the 7-seed Lakers hat, which uses the team’s “L” logo, meaning that all the purple and gold is condensed, which looks even worse. And then there’s the 16-seed, which has “Los Angeles” written in purple script on a black background. It’s an awful hat. You’d have to be three inches away from Leonardo DiCaprio to know what team he’s supporting. Its badness alone propels it to the West region final, because it’s just so flabbergasting that a celebrity would wear that hat.

2. Once again, Leo is ahead of the curve in terms of supporting a team: He wore a Golden State Warriors hat in 2004, before Steph Curry was even born (I’m pretty sure).

If we learn anything from this bracket, it’s that most of Leo’s best hat moments came while he was dating Gisele Bündchen. That woman really inspires greatness.

3. Not only did Leonardo DiCaprio wear a Washington State University hat in 2017, he might’ve also bought Nina Agdal one:

I briefly interviewed college sports expert Rodger Sherman about this oddity. He answered my questions with more questions: “Does he have a passion for Air Raid offenses? Does he like drinking a fuck ton of Fireball in the middle of nowhere? Is he a big Ryan Leaf fan? Is this Leonardo DiCaprio? Is this Leonardo DiCaprio?”

He then offered a summation: “The gist of Wazzu fandom seems to be devoting yourself fully to destroying your own body even though the team isn’t that great, because you’re in the extremely green and boring hills of Far Eastern Washington.” I suppose Leo finds that relatable.

4. The hat-only picture doesn’t show it, so I just want you all to know that Leonardo DiCaprio is one of those people who listens to the radio broadcast at sporting events:

Most Intriguing Matchup

Choosing between Leo’s baby blue UCLA hat (no. 14 seed) and his UCLA “B” logo hat (no. 3 seed) was not easy. The baby blue hat was part of one Leo’s trashiest Citi Bike uniforms ever: a pair of baggy cargo shorts, slip-on shoes, and a loose blue shirt with the sleeves rolled up. It was also what he was wearing when this happened:

But the “B” logo (for Bruins) could not be stopped in the West region …

Why This Hat Won

The “B” logo won because it is the tournament’s most extreme example of counterintuitive action in hat selection. Not only is UCLA’s “B” logo its least recognizable logo, but it also looks identical to the Boston Red Sox logo. To most, it probably seems more likely that Leo bought a customized Red Sox hat rather than a UCLA hat. (To wit: if you Google “Leonardo DiCaprio UCLA hat,” this hat won’t come up in the search; but you can bet it comes up when you google “Leonardo DiCaprio Red Sox hat.”) When Zac Efron saw him wearing this hat at a Lakers game in 2008, he must’ve been like, “Damn, bro. This Leo guy must’ve really become a Sox fan when he was filming The Departed.”

You can tell that Efron is not hearing whatever Leo’s saying here. He’s only thinking, “’Sup with that hat?”

The Midwest Region

Four Stray Observations

1. Wanna see a photo of Leonardo DiCaprio feeding a baby animal in a Notre Dame hat? OF COURSE YOU DO:

2. Leo’s Colorado State hat is just beautiful. The ’90s aesthetic, the brim bent to shit—it’s a really great hat performance. You may also notice that this photo is a very early entry to a series we talked about earlier, in which a beautiful woman hangs on Leo while he goes about his business.

3. Tough break for Wichita State (no. 2 seed) here. It’s a very random hat, and once again, Leo supported the team before it got popular—he wore the hat at the 2009 NBA Finals, and the Cleanthony Early–Fred VanVleet–Ron Baker Wichita State dynasty didn’t start until the 2012-13 season—but in the first round Wichita State drew Leo’s Cleveland Indians hat from 1993:

This hat may be patient zero for Leo’s love of hats, and it should be recognized thusly.

4. Rodger Sherman says Texas Tech is a “solid third-tier Texas school.” It’s random—like, regular old Texas would’ve made more sense, though I don’t think Leo likes the color orange—but it’s not that random. The most random choice would’ve been UTEP. Sherman is also smart to note that Texas Tech, like Washington State, is another college that employs the Air Raid offense. (Both teams have also employed Mike Leach as their head coach.) Leo loves them high-scoring teams, baby!

Most Intriguing Matchup

The Kansas vs. Kansas matchup is amazing. First of all, imagine a guy from California owning one Kansas hat. Then imagine that guy being like, “Ya know, I also need a black version of this hat.” Why? Why own two Kansas hats? Is this a matching concern? Does Leo like Bill Self that much? Doing this bracket has not answered nearly as many questions as it’s raised.

Anyway, the black Kansas hat (no. 13 seed) wins, because it’s way weirder and because in the full photo, Leo has a plastic bag strapped to his waist.

Why This Hat Won

The classic Michigan hat (no. 9 seed) is one of Leo’s most frequently worn hats. He’s worn it at tons of Lakers games; as we saw above, he’s worn it to tutor Zac Efron courtside; he’s worn it while strolling through New York City; he’s worn it with a suit jacket; he’s worn it while making out with Kelly Rohrbach as they wait at an intersection on Citi Bikes:

But most importantly, Leo wore this Michigan hat while he was shooting his shot at Rihanna at Coachella in 2016.

That photo is a work of modern art, on par with anything Botticelli ever painted. It is why the Michigan hat must win.

The Final Four

Here’s how everything plays out in the end:

The repeat uses and the spectre of a romantic rendezvous with Rihanna is too hard to ignore. Michigan may have lost Monday night, but it’s all good: The Wolverines won the Leonardo DiCaprio Baseball Cap Bracket. That’s just as prestigious.

Andrew Gruttadaro