As Kenny Rogers established long ago, life itself is a gamble. The odds are long, the stakes are high, and the house always wins, eventually. But it’s especially true for artists. After all, what could be a longer shot, a riskier enterprise, than pursuing a creative life as your livelihood? Now take that basic premise and multiply it by ten, and you’ll start to understand the mentality of a rapper.

Almost every rapper you know and love is a lottery winner who has hit an eight million to one parlay with dozens of legs. As such, it shouldn’t be a surprise that rappers tend to be gamblers. They’re young, rich, and many come from cultures where shooting dice on the corner, betting on the NBA Finals with classmates, or wagering whether or not your friend can sink a crumpled-up takeout delivery bag in a small waste bin from across the room is part of the rhythm of existence.

Hollis, Queens legend Ja Rule started off in the Cash Money Click almost 30 years ago, spent some time at the industry’s pinnacle building his Murda Inc. empire with Irv Gotti, and is now running a concert series in New York and launching his own $250-a-bottle cab sauv with a winery in Sonoma Valley. Ja is, historically, hilarious, and incredibly open and honest about his life and his past—and that includes his wins and losses as a gambler. Which is to say: He doesn’t hold back. Or as he puts it: “You’re talking to a real gambler and not somebody that bullshits. I gamble for real.”

GQ: Do you bet frequently?

JA RULE: I bet all the time. I love betting on games. I bet on golf. Football. Prop bets.

You were just in Las Vegas a few nights ago. How does going to a casino in Vegas work when you’re famous? Do you gamble with everyone else or do they have a special area where you can get some privacy?

I do both. Sometimes I go get the private tables when I want to just lock in and really try to take down the house because I’m playing high limits. And then other times I like to go and have fun amongst the people because that’s really fun too, betting on them. They get energy from that. When you go out and bet at the live tables with people, they don’t really allow pictures on the floor. So it’s kind of a win-win.

What’s the most you ever made gambling?

Oh, man, a couple of hundred grand.

What was it on?

A couple of things: Basketball, Super Bowl, stuff like that.

When you win big like that, how does it happen? Is it a parlay? Moneyline?

Betting the spread, moneyline, parlays, all the above. But usually when I win big like that, I bet big and I usually take the moneyline or take the spread. I don’t usually play parlays for big money. I play small money on parlays and shit and hope to the gambling gods we win.

Is there one bet in particular that you can remember winning big?

One time I was in, I want to say Australia, and I made maybe 100 grand at a craps table. That was a good time. I was shaking them things all day. And the crazy thing— I had to do a TV interview, and I completely blew it off. You never leave the table on a heater.

How about losses?

I remember a time when me and [Irv] Gotti, we bet, like, a couple of hundred grand on a basketball game, and Gilbert Arenas killed us on the spread. We was fucking with him, heckling them. At the end of the game, he took this shot in hopes and desperation to backdoor cover the spread—because they couldn’t win the game—but he took a half court shot just to fucking destroy us, and we lost our money. I’ll never forget that ever in my life. He fucking punished us that day, man. Big shout out to the Hibachi.

That’s the up and down flow of gambling. You go through that shit time and time again. Gamblers, we got all kinds of ways to try to get it back. Once we lose it, it’s a slippery slope. That’s why I don’t gamble as much as I used to.

What are you into these days then?

I like fantasy football. I’m big on that. We play fantasy football for big money. I play with a really cool group of guys like CC Sabathia, Michael Rapaport, Joe Budden, Bun B. I won this fucking year, just to let you know.

What’s the buy in for the league?

I think we’re at maybe like 10, 15 grand? Something like that. We went up a few times.

Is it an auction or snake draft?

Snake. I play in another league where we play the auction. But nowadays, that’s how I like to gamble, more amongst friends. I’d rather see a friend of mine win 100 grand from me than the fucking casinos. Because I have all kinds of ways to get that back. We can play golf on the golf course.

You bet on golf?

Oh, yeah, we bet on the golf course. Hell yeah, we bet skins. When you’re a gambler, you gamble, man.

What’s the most random thing you ever gambled on?

I learned how to gamble coming up as a young kid in the hood. We used to gamble on everything. Pitching quarters. We gamble on that. We used to play skelly. That was like the culture amongst the friends that I grew up with. We gambled a lot, and that translated into our lifestyle and how we did things in life.

Just becoming a rapper was a big gamble, man. A lot of my friends, we talk about that, and they talk about how I’m fearless in that way. I’ll take a risk. I’ll take a gamble. And it’s probably because of how I grew up as a gambler, and how I’ve lived my life.

Are you nice at Cee-Lo?

I’m incredible. You ask some of my friends. They won’t even pick up three dice around me no more. It’s ridiculous.

Do you have any philosophy to gambling? You mentioned craps, do you have an approach to playing?

I definitely have an approach to it. It’s all luck of the dice, but I play the numbers. I also play the hard ways. I’ll play the outside, inside, or all of the numbers. It depends. And then see, here’s where it gets tricky. Sometimes I will go in on the “Don’t Pass.”

Oh wow. You’re that guy?

[Laughs] I will play with the house sometimes and still play the numbers, roll the dice for a while, hit my numbers, hit my numbers, and still be betting on that. It’s weird, like, sometimes I’ll put it on the don’t pass and if I roll a six or eight, I’ll take it down and go with my roll. But it doesn’t matter because I’ll have money piled up on the hard ways. So hopefully I roll a hard ten. It’s all just trying to maximize your odds. It’s a little bit of a system that I have, but nothing can save you from losing money. Play at your own risk, people.

What’s your favorite sport to gamble on?

Football, because you get that whole week to make your picks, get your study in. I like the slower pace to figure out what I’m doing, calculate a little bit, try to make the best bet.

When you bet, do you use a bookie? An app?

I do use an app. But I ain’t biggin it up! They don’t pay me. Anybody got deals with these guys? Hit me up. I’ll let you know what app I use. I’m a hustler, baby.

Do you have a team that you go back to when you’re betting?

When you bet, it’s tough in situations where you have favorite teams. You’re gambling with your heart. It’s never good to do that. You got to gamble with your mind. So I try to stay away from that, but I do it sometimes, and sometimes it pays off in big ways. Like, the Giants are my favorite football team, so naturally, I bet the Giants beating the Patriots, and fucking came up pretty good on that! So those types of times are always good when you bet with your heart. But the problem then is when you bet with your heart and lose.

I rarely touch the Knicks. I feel the same way as you. I prefer not to gamble on the teams that I like, because then when you lose, you lose double.

I mean, if your team is the Golden State Warriors, you’re good. You can gamble on them. But when you see the Knicks and the Jets, you better be careful.

How about players?

Yeah, Jordan killed me in my lifetime. Going against him, betting amongst friends and homies and shit like that. And I used to always bet on the Knicks and lose. But as I got older, I bet on the Kobe and Shaq Lakers, they made me good money. Steph and Golden State, I love betting on them. They always covered.

But like said, I’ve slowed down a lot on that type of gambling. I don’t really gamble like that as much as I used to. I do it more now to scratch my itch, you know what I mean? And I put the bigger gambles on my investments, because to me, it’s the same. It’s like gambling. You do these startups, any investments and you see what happens. In three to five years, you hope you pick great companies and great teams that run these companies and you see what happens. I think that’s the progression of the gambler. When they start making real money or having real money, they start gambling on companies and businesses. It’s the gambler spirit, man. The gambler’s mentality.

I love that idea. Unfortunately, I feel like a lot of bankers and stock brokers have the same mentality.

Yeah, they’re all hustlers and gamblers. You can believe that. Trust me. I know a lot of hedge fund guys. We bet on all kinds of shit. And they’re good too. They’re good at making the right bet and that comes from the gambling. You gotta do your research. Some people just gamble blindly. Like, I like this team, I bet on this team. And that’s “fun” gamblers. But when you start getting into gambling, you really get into the nuances and the intricacies of, “Is this player going to play tonight? What refs are in the games?” and get into all that shit.

But see, now you’re not just making a bet, you’re hedging your bet. And now it starts to become a business. And when you’re doing business, it’s the same thing. I’m not just going to make a bet. I want to hedge my bet. I’m going to do the research on these companies and see and know what, and who, I’m actually betting against and betting for. So I can say a lot of those skill sets came from gambling.