Since breaking out as an aging stoner in Dazed and Confused, McConaughey has had more incarnations than the iPhone. He was a lovable rom-com staple for much of the aughts before a career drought forced him to reinvent himself as an oddball character actor in films like Mud, The Paperboy and Killer Joe. It was a sharp left turn that laid the groundwork for what became widely known as The McConaissance, a magical run that included unexpected turns in Magic Mike, True Detective, Wolf of Wall Street and that culminated with a Best Actor Oscar for his transformative performance as Ron Woodruff in the HIV drama Dallas Buyers Club. His newfound movie stardom, coupled with his enduring offscreen persona—that of a perennially shirtless, bongo-playing, catchphrase-spouting Texan—helped make him one of the most instantly recognizable people on the planet.

But not everyone is familiar with the tao of McConaughey. When Baltimore high school student Richie Merritt was literally plucked from outside his principal’s office and flown to L.A. to test for White Boy Rick’s title role, his first order of business was reading with McConaughey, who had already signed on to play the character’s father. Merritt and McConaughey first met in the parking lot of a bowling alley, and as far as Merritt was concerned, the man standing in front of him might as well have been the valet guy. “He had no idea who I was,” McConaughey tells Playboy of his young costar. “But part of his innocence and ignorance of not knowing who I was and not having the reverence for me or biography on me, not being a film guy who dreamed of being an actor, all of that was part of what was just right on the money for him being right. He had the confidence to behave honestly in front of the camera.”

Directed by Yann Demange and hitting theaters Friday, Sept. 14, White Boy Rick is the incredible true story of Rick Wershe Jr., a teenage drug dealer who became the youngest-ever FBI informant in 1980s Detroit. McConaughey stars as Rick Sr., a well-intentioned but hapless father who moonlights as a gun dealer and dreams of one day opening a video store so that he and his family can leave their life of petty crime behind. But it becomes quite clear from the film’s outset that despite his cockeyed optimism, Rick Sr. is something of a putz, a ne'er-do-well for whom the American Dream will always be just slightly out of reach. In other words, this is McConaughey like you’ve never seen him before—this is McConaughey, the loser.

“I usually play people that handle the situation, even if it’s not good for them. [True Detective's] Rust Cohle, [Gold's] Kenny Wells—there’s a whole bunch of them. But I’ve never played someone that loses so much,” he says. “There’s a sobriety to it. And what I mean by that is, these people are just doing what they gotta do to survive. These are people living on needs, not wants. There’s a difference. This is not a privilege. It’s a necessity. And this guy is surviving on the hopes and the dreams of the future.” But despite his character’s propensity to lay waste to everything around him, McConaughey stops short of calling him the L-word. “I don’t play a loser. I play a guy who’s trying to win but keeps losing. That’s the struggle. He can’t cut the mustard. He can’t tow the line. Every scene I’m in, I lose. Someone said the other night, ‘Is this story about redemption?’ And I was like ‘What? Redemption? Hell no! Everybody loses!’”

When I ask McConaughey if he used his own experiences as the father of three to help inform his performance as Rick Jr.’s dad, he flashes a lazy smile before answering, “It’s safe to say, without even knocking on wood, that I’m a better dad.”

But Rick Sr. does love his kids. I guess sometimes love just isn’t enough?

“That’s a great way to put it. It’s the first time I’ve heard it. That part I brought, which is the unconditional love and support. Family means a lot to me, and here’s a guy, who all he wants is to have his family together. His heart’s in the right place. He’s got all the ‘want to,’ but he just ain’t got the ‘can do.’ He comes up short every time.”

It’s when he shared scenes with the young Merritt—who had never even taken an acting class, let alone starred in his own movie—that McConaughey’s paternal instinct really kicked in. After all, it was 25 years ago, after being spotted in a Texas bar, that the then-non-actor found himself in front of a camera on the set of Dazed and Confused. “The challenge for me, part of the rodeo for me, was that I knew he didn’t know the rhythms of actors, he didn’t know certain things that we instinctually understand and set each other up for. He didn’t know what a mark was. I had to talk to Richie Merritt. I had to get to Richie Merritt’s heart." 

How did you that?

“I noticed early on how much family meant to him. So anytime to get him back on focus or get us in line or to be present in the scene, I could bring up family to him. I could share about my own family, or ask him about his own family, and it would just center him. He’d be right there. Another great thing is that he’s meeting a guy named Matthew McConaughey in the parking lot of a bowling alley, and he’s going to play his dad for the next five months. That’s about all you need, man. His understanding of me is based on the guy he met in the parking lot in the bowling alley, to right now. That’s really what it is.”

At its core, White Boy Rick is a tragic story about a father and son, which is what attracted McConaughey to the role in the first place. But it’s also a bracing look at late-20th century urban America, which was in the throes of the crack epidemic. To understand what life was like in Detroit’s gritty east side during that time, McConaughey visited Rick Jr. in prison, where he’s serving a life sentence (he was granted parole in 2017). There, the two men bonded over their respective families. Rick Jr. even made paintings for McConaughey’s kids that are hanging in the actor’s house to this day. But what struck McConaughey most about Rick Jr. was his honesty.

“I’ve talked to many people in prison, and 99 out of 100 tell you that they are innocent,” the star says. Rick Jr. also admitted that even though he knew that what he was doing then was wrong, he had one helluva time doing it. Still, it was important to both McConaughey and Demange to not glorify a life of crime. “There’s a seduction thing in people being outlaws, people who live by their own rules,” Demange tells me. “That’s always been fascinating for everyone. But I was very careful here to not sensationalize crime. It’s bullshit. I had to be honest in showing the excitement at times of the partying, of the aspirational side of it. You have to remember that I’m looking at it through the eyes of a 15-year-old who's going, ‘This is fucking fun,’ because that’s all Rick told me, how much fucking fun he was having. But I’m not going to sensationalize or glamorize the life.“ McConaughey agrees. “That’s why I was a fan of the script, and I’m a fan of the movie,” he says. “It’s not glorifying, and it’s also not sentimentalizing. It’s saying these are real people in real circumstances.”

McConaughey has been somewhat reluctant to get political in interviews after drawing heat for some post-election comments in which he said we should give Trump the benefit of the doubt, but I decided to end our conversation by asking him whether or not he hopes this film sheds light on the imbalances in the criminal justice system. “You can take that from it. I don’t know if there’s a statement, but you can that from it,” he says. “The parking-lot talk when you walk out of the theater can be about a lot of things. It can be about poverty, mandatory sentences—it can be about a whole bunch of things that are relevant." 

Do you think Rick Jr. should be set free?

“Look, there are a lot of people who dealt a lot more, that came in after him and have left before. There are murderers that have come in and left. Then you gotta go, ‘Jeez, how many other thousands are in here that just don’t have a spotlight put on their case?’”