Jelly Roll on Covering Toby Keith’s ‘Should’ve Been a Cowboy’ With T-Pain for Amazon Music, Plus Stagecoach, the ACMs, New Music and Social Media (EXCLUSIVE)

Chris Willman
·12 min read
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Jelly Roll might not have grown up on “Gunsmoke,” Roy Rogers and Gene Autry, the way the narrator of Toby Keith’s massive 1993 breakout song “Should’ve Been a Cowboy” did. But when the Western-wear fits, wear it. The rapper-turned-country music superstar has covered the late Keith’s signature song for an Amazon Music Originals exclusive, coming out the same day he’ll sing the song at the Stagecoach festival in California — joined for both the studio version and the festival appearance by no less a cowboy than T-Pain.

Jelly Roll got on the phone with Variety the day before the release of the cover (hear the stream, above) and his Friday night Stagecoach appearance to talk about the Keith tune, which benefits the late star’s children’s cancer charity. It sounds as though fans can expect at least one new song during his performance, as well, which, like many of the festival performances over the weekend, will be livestreamed on Amazon Music. He also discussed his first-ever nominations for May 16’s ACM Awards (four in all, iincluding entertainer of the year), and whether he’ll be returning to social media any time soon, after his decision to take a time-out belatedly created headlines of its own.

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Did Amazon come to you and said, hey, we have this idea for this Toby Keith cover, or how did it come about?

No, actually, Amazon just came to us and talked to us about partnering for something cool for Stagecoach and, as I was flipping through the ideas, I had been covering “Should’ve Been a Cowboy” for about a year now at most of my shows, just kind of honoring Toby as he was getting sick before he passed away. Then I really started chewing on, man, what better place to honor Toby than Stagecoach? Plus, Toby Keith was one of the artists that from afar, even though he would never have known it, encouraged me to do country music.

How so?

Just with songs like “Should’ve Been a Cowboy” or “The Next Thing on My List” and “I Love This Bar” — just the whole way he put his personality into his music. He was an outlier. He was unapologetically Oklahoma. There are a lot of things he did that encouraged me and empowered me. He was very individualistic and carved his own path and he did it his own way, from pillar to post. He never knew it, but he was a mentor to me, just watching him from afar.

You are a little too young to have grown up on “Gunsmoke,” like the guy in the song did, but you related to it nonetheless.

I love nostalgia songs in general, songs that take you to a place in time or have a setting. And that’s kind of another reason we picked it for Stagecoach. I mean, dude, think about it, in the middle of the California desert, 80,000 country music fans, what better place to sing “Should’ve Been a Cowboy.”

How did you wind up getting T-Pain on there?

I love T-Pain and I love his work and I was thinking about who would be a perfect surprise guest for Stagecoach that nobody would see coming. I love putting together odd pairings, because I think I’m an odd pairing by myself. And I think Toby was kind of all about that too. And then when I got to talking to T-Pain about Toby just in general, he was telling me the story about how the only time he’s ever done something big in the country space, at the CMT Awards, he was presenting with Toby [in 2009]. And he was just talking about just how awesome Toby was just as a human and how Toby made him feel comfortable and was cracking him up before they went out.

And I think also when he covered that Chris Stapleton record (“Tennessee Whiskey”), I don’t know if I speak for the whole country music community, but I’d definitely seen it and was like, wow, this is incredible — just what a raw, pure voice. I think T-Pain got a bad rap for his voice for so long because he leaned into Autotune but never really needed it. So it just seemed like a really cool pairing and a totally different look on the song.

T-Pain agreed and so did I — it just showed who he was again— that all the proceeds from this song will go towards the Toby Keith Foundation, to help kids with cancer. I just figured that we’re doing it for Toby and the cool thing was, I called T-Pain with that and he didn’t hesitate.

I’ve been covering the song and Toby’s son saw me at the CMTs and took me to the side and said, “Hey man, I want to let you know I’ve seen a video of you covering this song, and I think it’s one of the best versions of it ever. And I think you honor my father.” And it just meant so much to me.

You guys did not go for the Autotune thing on this song, so nobody should expect that.

No, no, no, no, no, no. I’m telling you, man, T-Pain can really, really sing. I dunno if you’ve seen the “On Top of the Covers,” but go watch it on YouTube. He covers 10 or 12 songs at a speakeasy in Vegas and it’s just him and a band, and, dude, his voice is undeniably incredible.

This is your first time at Stagecoach, this weekend. Do you expect you’ll get to hang out with anybody on your night there? Eric Church and Elle King are also on the main stage Friday night.

Well, I’m gonna hang out for the weekend too. I’m a such a country music fan. We blocked this weekend off last year, even if we didn’t get to play, just because we were gonna come and just experience it. So we’re hanging. And the cool thing is, Eric Church is a mentor and a friend, I look forward to seeing him. I look forward to talking to Elle. I look forward to seeing Miranda Lambert’s set, Nickelback’s late night show. Diplo… I’m gonna be giving hugs away, like the CMT Awards [where the promise of Jelly Roll hugs was a bit in Kelsea Ballerini’s opening monolog].

It’s nice you booked the whole weekend. A lot of people don’t think to do that and then they kind of regret that they have to jump right back on the bus.

Oh dude, I’m flying my daughter out, and you think I was gonna miss the chance for my daughter to see Miranda Lambert headline Stagecoach? [Lambert performs Saturday night.]

You had Flavor Flav introduce your show in Detroit Wednesday. He was in the news today just for talking about you on social media and responding to the stories about how your wife said you had been cyberbullied, and he’s obviously quite a fan of your personality as well as your music.

He’s a sweet human, man. His wife is just salt of the earth. I met their whole family again last night. I’ve gotten to really spend some time with Flav and his family, and they’re real, real salt of the earth.

Anything to update about what he was talking about, where your wife had mentioned that you were off social media? Do you think you’re gonna stay off, or is that just like a temporary thing and you’ll be back?

Oh man. I’m sure I’ll be back, but right now I’m not thinking about anything but just how I’m gonna honor the TK Foundation and Toby’s family. And we’ve got bigger fish to fry, man. I don’t hate social media. And…

I probably shouldn’t elaborate on this because nobody on my team wants me to, but I don’t have a problem with social media. And it wasn’t just bullying that did it. It was not only the toxicity of social media, but the addiction of it. I was becoming too busy to waste hours of my life scrolling. I can honestly say that I’ve been off social media for a few months now and I’ve never felt better or healthier mentally — never felt more clearheaded. I’ve also never had less of an idea what was going on in the world, but I tell you what, I’m definitely not coming back before the election. Bad joke.

No, that may be helpful advice for people… Also in Detroit, you did a new song, “Liar.” So was that just out for a test drive in Detroit, or might Stagedoach hear that?

I feel like if I did it at Stagecoach, it would be its real debut. I’ve been trying new music on the road. I’m a huge comedy fan and I was telling my manager, I was like, I’m a little jealous of my comedian friends. They get to try jokes out in front of people to see if they work before they put ’em on Netflix. So I kind of wanna start doing that more as a musician.

So people might hear something new at Stagecoach.

Yeah, I think we’re gonna. I tell you what, I don’t know what every other artist does when they debut at Stagecoach, but I have taken it serious. I rehearsed more for Stagecoach than I have any single event in my career.

Really? You have done so many shows that you should be in good fighting trim. So what made you think that you had more work to do?

I’ve got 45 to 50 minutes, which is a tight window, and I want to make sure I get across the fullness of who I am as an artist, like a real Jelly Roll show. I spend a good portion of the set getting people to understand where I come from and why I do what I do, and it takes a little time to develop that. It’s a premise that I have to set up throughout the show, so I’m trying to find a way to get that same message to people in 50 minutes.

People at Coachella are there to party, and yours is party-friendly music, but there’s a serious message underlying just about everything you do. So that’s probably an interesting balance for you to walk that line, where you don’t lose the reason why there’s a lovefest going on.

Yeah, that’s exactly right. You’re trying to find a way to tastefully do it and still stay true to who we are, but also keep people moving.

In talking with you at the CMT Music Awards, you said you thought that was the last time you’d be doing a song from your last album in a big TV setting. Anything more you’d say about that, since you do have got the ACMs coming up in May?

The four-time-nominated Jelly Roll at the ACMs! It doesn’t sound real. No, I’m telling you man, moving forward, it’s all new music. You can tell that because I’m teasing songs at club shows. I am sitting on a phone full of songs that are screaming to get out. I’m experiencing that artist patience thing for the first time in my career. I’m calling my manager and label every day, like, when can we leak a song? I think I might have to go back to my “ask for forgiveness, not permission” model.

So people on your team are trying to strap you down…

No, no, not really. They don’t care what I do. They’re cool.

A fun favorite stat about the ACMs is this marks the first time since the early ‘90s that someone’s gone from having no nominations one year to having an entertainer of the year nomination the following year. That happened with Billy Ray Cyrus 32 years ago.

You know, the statistic that nobody gives me when they give me that statistic, though, is, did Billy Ray Cyrus win it that year?

We will have to look that up. That would be a big leap.

Hold on, hold on, hold on. We’ll do it together. Watch this. [He speaks his phone.] “Did Billy Ray Cyrus win entertainer of the year?”… He did not win entertainer of the year. Well, I know it’s a super long shot for me to win that award, but I think I would be the first one to win it in that case, too. Well, you know what? He actually was nominated six times; never won one. American Music Awards, won three of 10 nominations. Two times won a Juno award. Six TNN awards. Two CMAs. He won a Grammy in 2020, and that’s the only time he won. He didn’t win for “Achy Breaky Heart” or “Romeo” with Dolly, but won for “Old Town Road” [for his featured appearance on the Lil Nas X smash]. Crazy, man. I hope it doesn’t take me until 2054 to win one.

With the roll you’re on with every other awards show, it doesn’t look like it’s going to be Billy Ray part two.

Being nominated for an ACM is a really big deal… I’m honored to just be in the building. All I want to know is, are Garth and Dolly coming back as the hosts? That’s the real million dollar question here.

They just announced it today. Reba has come back to do it this year.

Really? See, I’m not on social media. Thanks for telling me. I’d never know.

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