I learned to love eight-ball pool early, at the edge of a gleaming Brunswick table in the corner of my great-grandmother’s basement. The table was for adults, and I wasn’t allowed to touch it, but sometimes my grandfather would let me get the balls out. He taught me a rudimentary bridge, how to draw the cue back straight. Though I didn’t yet understand the rules of the game, the mystery cult of pocket billiards lodged deep in my brain.

In 2021, during the second pandemic summer, I joined an eight-ball pool league in Chicago. I started playing with them because I wanted to get better; I stayed because of the people I met. The lively community of players in Chicago come from all walks of life. Every Tuesday I shot alongside a livery driver, a chef, and several bartenders. I’ve played a vintage-furniture salesman, an advertiser, a high-school teacher, a real-estate agent, a train conductor, a political-campaign worker, a chocolatier. We play in a bar with two heavy wooden tables that are only slightly younger than the city of Chicago itself. The bar’s owner makes his own cues in the basement on an ancient lathe. These shooters in Chicago share a love for the game, an affinity for cheap beer, and an almost universal appreciation for the bitter Midwestern spirit Malört. But what really brings us together is losing. A lot.

When a game starts, scratch risks loom everywhere. A scratch gives the opposing player ball-in-hand privileges, meaning they can pick up the cue ball and place it anywhere on the table to set up their next shot. Skilled players can use a ball-in-hand opportunity to run the remaining balls off the table and win the game.

Early on, I scratched all the time. I shot too hard and ricocheted the cue ball into a pocket. Ball-in-hand. I hit my opponent’s ball before my own. Ball-in-hand. After a shot, a ball didn’t hit a rail. Ball-in-hand. One memorable (rare) time, I was given ball-in-hand because of my opponent’s mistake. I lined up a straightforward shot into a corner pocket, hoping, after I made the shot, to knock the cue ball into position for the eight ball. This required me to put draw, or backspin, on the shot. Instead, out of sheer nerves, I hit too hard and scooped the ball up with my cue. It went airborne, hopped over the ball it was supposed to hit, and sailed neatly into the pocket. Ball-in-hand.

Pool is the most humbling game I’ve ever played because your mistakes are obvious and all your own fault. Every pool table is crosshatched by failure: past missed shots, errant cue balls. It’s a fickle game, and even the best players make mistakes. Success comes down to some concoction of nerves, timing, luck. Bad losses are immortal; wins are forgotten. Pool is a game of losers who hate losing—who hate it so much they keep playing. It’s no wonder it’s often associated with gambling; a game that involves so much failure needs other stakes than pride alone.

In the stairwell of a pool hall where I often practice hangs a faded poster for The Color of Money, Martin Scorsese’s 1986 pool drama starring Paul Newman and Tom Cruise. The film was shot all over Chicago, including the pool hall where its poster hangs. This pool hall takes up the entire second floor of a nondescript building on Chicago’s northwest side. Forty tables of various sizes fill the space. Plastic flaps separate each room, like it’s a meatpacking plant. On screen, I recognized the scuzzy light of the place, the numbers above the lamps illuminating each table, and the tall wooden chairs. The film follows the often-confrontational partnership between Eddie “Fast Eddie” Felson (played by Newman, who reprises his role from 1961’s The Hustler) and Tom Cruise’s character, Vincent Lauria. Unlike most sports films, losing, not winning, is the main thrust of the plot. To turn Vincent into an expert hustler, Fast Eddie teaches him to throw games—to lose on purpose to better con his marks. But beyond the thrill and the drama of the fake losing, Eddie’s actual losses are what I recognize most in the film. As the film progresses, Eddie, who was once a young phenom like Vincent, realizes he’s losing his edge. He gets sharked by a pool hustler named Amos (played by a young Forest Whitaker in one of his first film roles). Eddie refuses to quit even as loses game after game. Newman plays Eddie as quietly desperate in this scene. “Are you a hustler, Amos?” he asks again and again, already knowing the answer. Eddie’s inner turmoil only comes through via Newman’s eyes: they spark with defiance and cloud with shame. After the games are over and Eddie parts with his money, he crumbles, berating himself as Vincent looks on. He lets out a sigh that every pool player would recognize, the sharp exhale that comes with a weary acceptance of failure. “I gotta work harder,” Eddie mutters.

I’m not a hustler, and I could fool no one with my skills. But I’ve lost many games that I shouldn’t have. You wish you could rewind it, undo your mistakes, but you can’t; the balls are already re-racked for the next game. All in all, the stakes of losing a pool match are low for me. I don’t play for money, and the league is competitive but casual. But there’s still something about the bareness of it, how stark and stinging it is to watch someone else make their balls while yours sit. My fellow players taught me how to look at that bareness head-on. There weren’t tableside lectures on the nature of losing. They just failed in front of me, and I returned the favor.

After his failures with Amos, Eddie arrives at a pool hall in the harsh light of the next day to practice, alone. Lost in thought, he knocks a cue ball around an empty table as the camera pans back over a seemingly endless row of identical tables. The tables emanate a sort of tranquility, each one a blank slate.

In matches, when I finally pull my stick back to try for the eight ball, the cue ball sliding across the felt holds my attention. It holds the potential for success, but what I’ve learned is that success is often only delayed failure: sometimes the black ball drops, but not every time.