How Larry Bird’s Spirit Helped Ben Affleck and Matt Damon Hit It Big in Las Vegas

We caught up with the A-list actor and director and he told us a great story featuring him and his equally famous friend after a visit to Larry Bird's home.

Ben Affleck WynnBet 2021

Ben Affleck WynnBet 2021

Ben Affleck WynnBet 2021

If you gamble, especially on sports, you have a system. Some make bets based on stats, metrics, and meticulous research. Others rely on their eyes. Then there are the ones betting big based of a premonition.

Ask Ben Affleck to tell you his most memorable quasi-sports gambling story and it ends up having everything to do with a vibe he and Matt Damon—way before the two become uber-successful actors and filmmakers—felt after a pit stop in Indiana during a cross-country trek. The famous friends, who grew up around Boston, decided on their way to Los Angeles that they would say what’s up to Larry Bird by rolling up to the Celtics legend’s home in French Lick, Indiana.  

“So we drove up to his house, saw his basketball court, and were like, ‘Is Larry home?’” Affleck recalls. “Even though he wasn’t there—or maybe he was there and he blew us off, I don’t know, but we actually never saw him. Then we kept going and we were like, ‘Yo, we were at Larry’s house. It’s a sign.’”

Las Vegas is where the story picks up next and I’ll save the rest of it for below because, hey, we’re running a business here and you’re capable of scrolling. Just know the energy the duo felt when they strolled into a Sin City casino, and that Affleck’s felt numerous times as a well-chronicled card shark, is part of what he channeled in his latest directorial duties that you won’t see in a theater or if you fire up Netflix.  

Debuting Monday, you can catch Affleck’s work directing and starring in a spot for WynnBET’s new sports gambling app that features his pal Melvin Gregg, Shaquille O’Neal, Jennifer Lopez’s mom Lupe, and a cast of characters all imploring Affleck to subscribe to their unique betting methodology. You decide who steals the show in the 2:20 spot, but O’Neal’s performance, in particular, stood out to Affleck. Which is great since the king of commercials made sure he brought his A game for the A-lister.

“When they told me Ben Affleck was directing and my main man Melvin Gregg was going to be in there, I said to myself I have to step my game up,” says O’Neal. “So for the first time only, I memorized my lines because I just wanted to bring the energy. Bro, you can’t have a commercial directed by Ben Affleck and you’re stinking it up.”

We caught up with Affleck and Gregg—and few days after that O’Neal, but you can read that interview Tuesday—via Zoom to talk about filming on the casino floor, some sports betting dos and don’ts, their favorite sports gambling stories, and why they believe LeBron James and the new-look Lakers are legit.  

(This interview has been edited and condensed for clarity.)

Ben, I’ll kick it off with you. What was the coolest part of directing this spot for WynnBet?

Ben Affleck: I’ll tell you what, it was fun to shoot in the casino and to try to communicate and bring the energy the Wynn people wanted, the way sports betting with your friends can be fun, and communal, and try to give a sense of that energy and electricity that Vegas has, the Wynn in particular. So just communicating the fun of that experience of showing up in Vegas and meeting up with your friends and trying to profile all the aspects of the casino. Shaq was a lot of fun and he was improvising and he had great energy. Melvin, I just love as an actor, and I’m just lucky I got a chance to work with him. Any opportunity I get to work with him and spend time with him I always want to take. It was a great experience. It was a lot of fun.

Before I get to you, Melvin, I did want to ask why you handpicked Melvin. You kind of just laid it out there, but tell me what be brought to this specifically.

Ben Affleck: Melvin’s just a really, really good actor, you know, who I worked with on “The Way Back.” The first day we worked together I was—in the way that you are ever, you know, 10 movies or so—just taken aback and kind of astonished by somebody’s evident talent. That in the case of Melvin, combined with just a very, smart, funny, cool guy who I wanted to be friends with—and who’s talent I admired and career I wanted to be part of. All the positive steps in my career have tended to be gravitating toward people that I think are talented and mooch off their talent as much as I can.

Melvin Gregg: You can’t see, but I’m blushing right now. Thanks, Ben.

Melvin, are you as good at busting Ben’s balls in real life as you were in the spot?

Melvin Gregg: Ben is just a great guy all around. The amazing thing with Ben is you feel the energy around the guy.

And what did you most enjoy about filming the spot?

Melvin Gregg: : Just getting a chance to work with Ben. We got a chance to work on “The Way Back” as actors and getting to be directed by him is a dream come true. I’ve been watching him since I was like eight years old. To be able to be directed by him, just the energy, man, was just so much fun. It didn’t feel like we were working at all we were just in the car kicking it, laughing, making jokes, and we just happened to be working for the WynnBet casino app. And working with Shaq as well. I felt like a kid meeting his idol. It was a great experience, on and off camera.

Obviously the spot is centered around the gaming app and everything that Wynn’s doing in the sports betting world. So I’m curious how big of a sports gambler are you guys? And Ben we know your reputation as card shark.

Ben Affleck: [Laughs.] My father actually made a little book—not legally—when we were kids. I remember we got our first VCR. My father said, “You can thank Steve Grogan for that.” [Ed’s note: Grogan was the Patriots’ QB from 1975-90] Because in Boston, you had to bet on the Patriots so he made a lot of money with people betting on the home team, making book at this bar he worked in. So sports betting has always, to me, been part of the fabric and culture around my life. It’s always kind of been an aspect of watching sports that frankly makes it more fun. If you have $50 on the game and you’re watching, like me growing up when the Patriots were terrible and the Red Sox were terrible, the Celtics were good for a minute, watching those teams it made it more interesting if you had $50 on the game. Also I tried to bring that energy that Melvin would be so good at because part of it is like who would you most like to be friends with and hang out with and Melvin came to mind right away for that. I was like this is a guy that people will gravitate toward and respond to. And part of that was trying to communicate the energy that whatever it is about watching sports together and rooting for a team and the way that can be fun and competitive but also can bring out a lot of joy and pleasure from it. That’s why sports are so popular. That’s why everybody sits around watching football games and basketball games. It’s not always because they have some intense personal rooting interest. There’s a communal aspect to it. Part of that is always in my life I just always understood having a little bit of money on the game gave you a rooting interest.

Melvin Gregg: A lot of what Ben said. When you got something on the game the stakes are a little higher. You have skin in the game every play is heightened that much more. Like he said, it’s a communal thing. A camaraderie of guys getting together, girls getting together, whatever, kicking it, watching your favorite team or whatever game is on and having some stakes with bets is an experience. I just feel like WynnBet is adding to that experience.  

One of themes, or plots, of the spot is your allegiance to Boston. Have you ever bet against one of your squads? Some people will while others think that’s a cardinal sin of sports gambling.

Ben Affleck: There are times I haven’t bet on my team. But I don’t bet against them. Although, there are definitely times when, like any sports fan, you’re more or less happy with your team or the choices they’re making or frustrated by it. The satisfying thing about betting is when your team is good and the Yankees fan not only is humiliated by the loss, but has to reach into their pocket.

There are characters in the spot that implore you take their advice because they have a system. Do any of your friends have crazy handicapping systems they try to convince you work?

Ben Affleck: That’s one of the wonderful and terrible things about sports in general. Everybody’s a fucking expert, you know what I mean? Everybody’s absolutely convinced they’re absolutely right, right up until they’re not. One of the things that I thought was fun about the concept for this was the way when you’re trying to figure out which way to go. Some people have their weird systems they work out, some people think they get signs from the universe, whatever random shit shows up on their Instagram feed they decide, “Oh no, I gotta go with Kansas City.” The way it brings out people’s idiosyncrasies and their personalities. Like if you’re a very logical, focused, front-brain math person you’re going to approach it that way. If you’re somebody into astrology you’re going to approach it another way. I tend to think a lot of it has to do with, I fall in the category that sometimes you get lucky, sometimes you don’t. Sometimes you’re looking fastball they throw you a curveball and that’s just the way it goes. That being said, that unpredictability and uncertainty about it is what’s fun. And the fact it brings out all these aspects and personality traits about who we are underneath is revealing. I was trying to illustrate that in a fun way with all these characters. The hard part was trying to squeeze it all in.

Do you guys have a favorite sports gambling story?

Ben Affleck: One story that’s semi-sports betting. When I first moved to LA, Matt Damon and I drove cross-country. We stopped off at French Lick, Indiana because we thought we were going to go to Larry Bird’s house. Now, I would discourage people from going to the personal homes of people they admire. But we went to French Lick and we were like, “Where does Larry Bird live?” So we drove up to his house, saw his basketball court, and were like, “Is Larry home?” Even though he wasn’t there—or maybe he was there and he blew us off, I don’t know, but we actually never saw him. Then we kept going and we were like, “Yo, we were at Larry’s house. It’s a sign.” So we stopped in Las Vegas and we’re going to make one bet, we’re going to each put $500 down, which at the time was like an irresponsible fraction of our total net worth to be betting on a roulette number. But we did it nonetheless. And I swear to God, I shit you not, we walked into the casino, put the money down, looked around for the roulette tables. Both of us bet $500 on No. 33 and it fucking hit. We walked out of there like, “We have to leave Vegas now, we can’t make anymore bets.” Got back in the car and went back to LA and felt rich. We were sure it was the spirit of Larry Bird and our pilgrimage to see him.

How about you, Melvin?

Melvin Gregg: I can’t top that one. That’s tough to top. Imma bow out. That’s a great story.  

Alright, so tell me, Melvin, as a Lakers fan, why they should be odds-on-favorites to win the Western Conference?

Melvin Gregg: I mean, look at the lineup. We got some great weapons. LeBron is fully rested, AD is fully rested, you saw what we did the year before last. We weren’t healthy this year. Carmelo Anthony, come on, the chip on his shoulder.

Eh, lot of old guys.

Ben Affleck: That’s what they said about Tom Brady, mother fucker.

Melvin Gregg: Exactly. It’s about experience.

We’ll end it on this. Ben, you’re known as a Patriots fan. Their over/under is 9. What are you taking?

Ben Affleck: That one I’m going to have to, thanks to set of complicated allegiances, recuse myself from offering my opinion. I will tell you I think the reason the oddsmakers like LA is because LeBron, like Tom Brady, like [Michael] Jordan, like Kobe [Bryant], like Shaq, like Larry Bird, like Magic [Johnson], those great players that can do more than just put numbers up, but do something for team cohesion and make other people better and are team leaders tend to win. Even the actuarial, math-minded linemakers recognize the intangible aspects of what that leadership means. That’s why I would never bet against Tom Brady and I wouldn’t bet against LeBron. LeBron is that kind of special player that just seems to elevate people around him, like Jordan, like Kobe. In fact, the best sort of betting tip for sports I ever got is to bet on great leaders.

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