Lil Skies has been on an incredible run lately, and one of his biggest moments yet was the release of a Cole Bennett-directed video for "Nowadays" featuring Landon Cube.

Shot in Bennett's old high school in Illinois, the video had to overcome a series of obstacles to actually see the light of day, though. In a new interview with Billboard, Bennett explains that he had to trust his intuition and fund the video out of his own pocket before battling with his local school district to get it released.

"We were originally going to do another song off the mixtape, 'Big Money,'" he says. "That’s what the treatment was written for. But I had a feeling about 'Nowadays.' I thought it could be big, and also the setting and this treatment, I felt like it fit 'Nowadays' more than 'Big Money.' Also, I was like, 'I don’t want to upset the school. I feel like ‘Nowadays’ has a better message to it.'"

According to Bennett, the label was set on the idea of shooting "Big Money," so he took matters into his own hands: "I was like, 'You know what? I’ll pay for this out of my pocket. We’re doing 'Nowadays.' I don’t give a fuck. Cancel the budget. I have a feeling about 'Nowadays.' We’re doing ‘Nowadays.'"

After shooting "Nowadays," though, Bennett's teacher called him and said the school asked to obscure its identity in the video because they didn't want to be associated with it. Then, they said they wanted to keep the video from being released altogether.

"I was in Europe on tour with Ski Mask, and my teacher was blowing me up on my phone saying, 'We can’t release the video. This can’t come out. We had a meeting with the school board, and everyone voted it down.'" Bennett says. "So I landed back in Chicago, and I typed up this three-page counter argument for every argument they could try to use about everything. Because I knew how big this was gonna be, and I knew how harmless it was—and keep in mind, they hadn’t seen any of the footage, or heard the song at all."

After speaking with officials at the school district, Bennett got a clearer picture of what was going on. The school didn't seem to be happy about getting associated with face tattooed rapper. Bennett says, "They were like, 'What would you think if you were a parent and you were thinking of putting your kid in Plano High School, and you saw a rap music video coming out with a kid with face tats walking down the hallway?' And I was like, 'What is going on? That’s the most stereotypical thing I’ve ever heard.' I was like, 'You guys haven’t seen the content, you haven’t heard the song.'"

Feeling that something wasn't right, Bennett looked into the situation and found out that the school district hadn't yet gone through the proper steps to ban the video from coming out.

"You need to have a public board meeting to make a decision like that," he says. "And they hadn’t had a public board meeting, they just spoke about it together. The next board meeting was like December 20th or 22nd, and I was like, 'Damn, I need to put out this video before that next board meeting, so they can’t legally ban this video.' And I was like, 'I’ll face the consequences when we get there, but I know I’m not doing anything wrong.'"

Realizing that the school district would likely be happy with the video once they saw a positive reaction from their students and the rest of the community, Bennett decided to put the video out before they had a chance to hold a board meeting and ban it.

"I wanted to release it Sunday so that all the kids at the school could be talking about it on Monday and so that all the school board members could hear how excited all the kids were," he explains. "‘Cause I knew how impactful it was, ‘cause that’s inspiration! It’s a very small town, so to see these kids’ favorite rappers in their high school, and now the song’s on the Billboard Hot 100—that’s crazy! And I don’t think the school sees all the benefits of it, but they saw it as, 'Cole Bennett’s doing a video here and in the past he’s had videos with guns...' And I was just, 'At Lyrical Lemonade, we have a positive message. My previous videos have no reflection on what I’m bringing to your school.'"

He was right. Bennett put out the video and the school said nothing when they saw the positive response. Now it has over 60 million views and Lil Skies' career is taking off faster than anyone imagined. Seems like he made the right decision.

If you haven't already, you can watch the "Nowadays" video at the top of the page and learn more about Lil Skies in the mini-doc below.

Continue for his thoughts on old heads, drugs, and "Red Roses."