Struggle Jennings knew Jelly Roll long before hardly anyone else did. The singer, songwriter and rapper has been friends with Jelly Roll since before either of them had flourishing careers, through the highs and lows of both their personal and professional lives, including their own time in prison for various offenses. Both Jennings and Jelly Roll also made music together in the past, including four Waylon & Willie albums, honoring Jennings’ grandfather, Waylon Jennings, and Willie Nelson.

Now, the two have combined their talents again, on their collaborative “Hard To Hate.” The song is from Jennings’ forthcoming Monte Carlo album, scheduled to be released in May.

“We have been best friends for 20 years,” Jennings tells Everything Nash. “We effortlessly make music together. We got in the studio, and decided to do something different than we had ever done. He’s been leaning more toward the country genre. I’ve got an album coming out that’s about 80 percent country; I’ve always integrated country into my rap. But I’m just exploring, and moving into the next phase of my life and my career. So we were like, ‘We’re gonna do one that’s just singing, just country.'”

“Hard to Hate” was inspired by their collective challenging pasts, and the hard battles they fought to get to where they are today.

“We were just sitting there having a conversation before we started writing, about all the things that we’ve let go of and the things that we just can’t let go of,” Jennings recalls. “The things in our life that we’ve let go of that are old ways and old habits, and then there are some things that you can’t let go of, ’cause they’re so dear to you. So the song started like that, and it ended up becoming what it was and I love it. It’s one of my favorite songs off the album for sure.”

Jennings and Jelly Roll’s friendship has gone through more tests and trials, and highs and lows, than almost seem possible. But it was their hard-fought struggles that make their relationship so strong today.

“Everything that two men can possibly go through together, me and Jelly Roll have gone through together,” Jennings previously told American Songwriter. “We’ve carried caskets, we’ve taken care of each other through jail and prison bids, we were on the streets together when music wasn’t on the up-and-up and we were hustling. We’re best friends.”

Jelly Roll has had quite a year, which includes his recent No. 1 hit, “Son of a Sinner,” breaking a Billboard record by spending 25 weeks at the top of the Emerging Artists chart. As Jennings continues to make his own mark in music, he remains Jelly Roll’s biggest fan, and strongest advocate.

“We’ve been friends for 20 years, and I couldn’t be more proud of him,” Jennings boasts. “This is definitely his moment. It’s well deserved and he’s definitely worked for it. It’s so exciting to see, and getting to see him get the recognition as an artist that I feel he should have gotten ten years ago. But watching it happen for him, and watching how he’s handling it … it’s making him a better person. He’s just become such an incredible person to be around. He always has been, but just watching this transition of his, and watching him shoot to the top has been a blessing. It’s been so heartwarming and I couldn’t be prouder of him.”

Find “Hard To Hate” and all of Jennings’ music, as well as a list of his upcoming shows, at StruggleJennings.com.