Jelly Roll moved to tears at sold-out American Family Insurance Amphitheater in Milwaukee

Jason DeFord dropped out of school in the ninth grade. His mother has struggled through mental illness and addiction, often staying secluded upstairs in her bed. He went to jail around 40 times, including on a felony aggravated robbery charge when he was a teenager, and missed the birth of his daughter while locked up. He was a drug dealer before he was an adult and became a drug addict himself.

And the Nashville native turned his life around. Stopped taking hard drugs. Never went back to jail after his daughter was born. Built a music career as Jelly Roll. Now 38, DeFord knows it's a blessing that he's not dead or incarcerated.

And to be on stage at a sold-out American Family Insurance Amphitheater in Milwaukee Friday, part of the blockbuster "Backroad Baptism" tour as one of country music's biggest breakouts of recent years — you could see in his eyes, he knew it was a miracle.

"I'm sitting up here with (expletive) goosebumps staring at all 23,000 of you," he said with a laugh six songs into his hour-and-45-minute set. "This is crazy, this is so (expletive) crazy."

Then he started to cry, turning away from the deafening cheers for a moment to wipe away his tears. He then turned back around, his eyes still watery, to sing "Son of a Sinner."

"Mistakes I made, I paid for them in cash. Walked a million miles on broken glass," he sang. "I'm feeling like I'm fading. My heart is slowly breaking."

As raw emotion poured out from Jelly Roll's quivering voice, a tough-looking guy standing next to me looked on, his right cheek stained by a single tear rolling down his cheek. He never wiped it away.

"This is real music for real people with real (expletive) problems," Jelly Roll said at one point. But this wasn't a concert, he said. "This is a family reunion of people healing together."

Admitting Friday he was going to have to fight to hold back his tears, Jelly Roll reflected on his mother's devastating struggles during a shattering performance of "She."

"I don't want to say goodbye. She can't get herself to stop," he sang somberly of her pill addiction. "And she feels like she's flying, while we're all watching her fall."

As he sang, the phone number for the Substance Abuse and Mental Health Services Administration hotline appeared on a screen behind him. "If you are here tonight and you are celebrating your recovery or your sobriety, on behalf of all of us, we want to say we're so (expletive) proud of you," Jelly Roll said. The star and fans together cheered on a fan with a sign announcing 422 days of sobriety at the first concert with their son, and another with a sign announcing their year-anniversary of being sober, as pictures of recovering addicts achieving several years of sobriety flashed on the stage's screens.

And during that song, and for finale "Save Me," it was clear Jelly Roll's fans weren't the only ones healing. He still is, too.

"I'm so damaged beyond repair," he sang. "Life has shattered my hopes and my dreams."

But in processing their pain together Friday, all hope was not lost.

"You changed my life in ways I would never guess. You changed my wife's life, you changed my daughter's life, you helped me break generational curses," Jelly Roll said Friday. "I can never thank you enough."

As heavy as this all was, that gratitude, from star and fans alike, took Friday's show to places of tremendous joy.

During a medley of songs that inspired him and offered needed solace when he was younger — including DMX's "Ruff Ryder's Anthem" and Eminem's "Lose Yourself" — the crowd was so smitten by Biz Markie's "Just a Friend" they sang the chorus again and again, a first on the tour, prompting belly laughs from Jelly Roll.

The crowd also got a big kick from an onstage appearance from Jelly Roll's wife Bunnie XO, a former sex worker turned podcast host and influencer, who Jelly Roll serenaded with the love ballad "Kill a Man."

Jelly Roll also resurrected a couple old Southern rap rock songs from earlier in his career like "Hate Goes On," delivered with plenty of bravado (and plenty of heavy lifting, as was the case all night, from a powerhouse seven-piece band).

Among the night's hip-hop performances, he was smoked by a 12-year-old fan with a sign that asked to perform his Brantley Gilbert collaboration "Son of the Dirty South" with him. The kid crushed it, firing off tongue-twisting rhymes like he'd been destroying stages in front of 23,000 people for twice his lifetime.

"That was incredible. It blew my (expletive) mind to be honest with you," Jelly Roll said with a laugh. "Boy son, if I had had that talent when I was 12 years old, I wouldn't have went to prison. ... It's going to be truly (expletive) hard to follow that, that sucks. We should have saved him for last."

Fortunately for him, "Need a Favor," from Jelly Roll's new country album "Whitsitt Chapel," showed up two songs later. Still resembling the authentic, edge-of-destruction singing and songwriting that's made Jelly Roll an unlikely phenomenon, but with more musical edge and a faster beat, "Favor" is the biggest song of Jelly Roll's career. The current Billboard Country Airplay chart topper also is the first song ever to also top the Mainstream Rock Airplay chart. But judging from the explosive energy from Friday's crowd, a breakthrough milestone like that seems to be just the beginning for Jelly Roll.

"I want you all to know I will never in my life do another tour and not come back to (expletive) Milwaukee," he said. "But you've got to fulfill a dream of mine. My dream is to play the arena right here in downtown. That's my dream."

I'm guessing that can be arranged. And along with an inevitable Fiserv Forum Jelly Roll show, I bet we'll see him headline American Family Field, too.

More: These are all of the arena, amphitheater and stadium concerts in Milwaukee in 2023

More: With big concerts with Morgan Wallen, George Strait and more, Milwaukee has become a must-play market for country music.

Yelawolf, Struggle Jennings and Josh Adam Meyers opened

Two acts closer to Jelly Roll than anyone opened for him Friday: Yelawolf, who Jelly Roll credited during his set for taking him out on his first tours and buying him dinner when he was broke; and Struggle Jennings, Jelly Roll's “best friend for 20 years” of ups and downs.

Yelawolf described himself Friday as a “country (expletive),” a “rock (expletive)” and a “hip-hop (expletive).” To argue his case, he went from belting Garth Brooks’ “Friends in Low Places” a cappella, to growling along to Pantera’s “Respect,” to spitting verses over Ol’ Dirty Bastard’s “Shimmy Shimmy Ya.”

But mostly he was a hip-hop, well, expletive, delivering rapid-fire rhymes over his DJ’s sharp record scratches for songs like “Pop The Trunk” and “Catfish Billy.”

After about half an hour he let country crash the set again by inviting the latest signee to his label Slumerican, Tony Martinez, sing a song. It was a risky move, especially since the little-known Martinez’s acoustic guitar was barely audible, but his commanding baritone kept the crowd captivated all the same.

“I just wanted to make sure you were awake,” Struggle Jennings (yes, he’s related to Waylon and Shooter) said early in his set after lending his blunt, gravelly voice to Carl Perkins’ Elvis Presley-immortalized classic “Blue Suede Shoes.” Yep, that did the trick — although a sprinkle of fiddle and zesty drum fills kept it from being a total disaster.

Attention seized, Jennings rapped through culture war-channeling anthems “God We Need You Now” and “Cries of the Crusader” with live vocals from surprise guest Caitlynne Curtis. But political persuasion was pushed aside for “Savior” and “Outlaw (Expletive),” where Jennings movingly talked about learning to take personal accountability for the mistakes he made while locked up in prison for five years — and proudly praised his daughter for avoiding her parents’ troubled path. She’s graduated high school with a 3.9 GPA, and next week Struggle Jennings gets to drop her off at college.

Comedian Josh Adam Meyers was the night’s loudmouth emcee, keeping the energy high with band-fueled antics like crowdsurfing over a sloppy cover of 4 Non Blondes’ “What’s Up,” and making a game of “make some noise” increasingly ludicrous, prompting shoutouts from people on high blood pressure medication and folks who pay for Hulu but never watch it.

He joined Jelly Roll during the headlining set, as well, to rap along to Afroman’s “Colt 45,” (part of an eclectic medley that began with folk traditional “The House of the Rising Sun.”)

4 takeaways from Jelly Roll's Milwaukee concert

• "Has the state of Wisconsin legalized marijuana yet?" Jelly Roll asked to a bunch of boos. "I'm from Tennessee ... and I'm still treated like a (expletive) criminal for smoking marijuana. It's insane. ... I'm not the kind of guy that talks about political (expletive) on stage. I don't have any education at all. ... But it amazes me that I watch big pharma profit trillions of dollars a year feeding families drug addictions. It blows my (expletive) mind in places like Wisconsin and Tennessee you can get a Percocet easier than you can get a bag of weed. It's (expletive) insane." Jelly Roll further called for recreational marijuana to be legalized in all 50 states, and that doctors should be incentivized "to prescribe THC and CBD more often than they prescribe narcotics."

• Along with the medleys, Jelly Roll also covered Lynyrd Skynyrd's "Simple Man" Friday, in tribute to the last surviving original member, guitarist Gary Rossington, who died in March. "I'm talking about the man who formed my childhood with these licks," he said. "The day he died I made a promise that every night I was going to sing to the holy heavens ... where Gary Rossington is watching us right now."

• Jelly Roll also dedicated "Smoking Section" Friday to a young fan who died from cancer in December and his family who was at the show.

• It's common for artists to express gratitude from stage, but few have seemed as profoundly touched as Jelly Roll, who offered effusive praise of his 61-person crew, and even praised the layout of the venue, marveling that he could see a lady's pink sign all night on the hill behind the seats. And he offered a rousing speech to his fans to express his gratitude: "Thank you for buying a ticket. Thank you for paying that stupid-(expletive) fee they put on all these tickets these days. ... Thank you for sitting in traffic. Some of you thought you were going to miss the show it was so (expletive) bad. Thank you for waiting in line. Thank you for paying too much money for a beer. Thank you for having to walk all the way around this big (expletive). Thank you for (expletive) every single headache you went through to be at this show tonight. ... Thank you all, man."

Jelly Roll's American Family Insurance Amphitheater set list

1. "The Lost"

2. "Hate Goes On"

3. "Halfway To Hell"

4. "Creature"

5. "Dead Man Walking"

6. "Son of a Sinner"

7. "Boys in the Hood"/"Ruff Ryder’s Anthem"/"Lose Yourself"/"Just a Friend"

8. "She"

9. "Smoking Section"

10. "Unlive”

11. "Same (Expletive)"

12. ”Son of the Dirty South”

13. "Bottle and Mary Jane"

14. "Need a Favor"

15. "The House of the Rising Sun"/"Hurricane"/"Colt 45"

16. "Wheels Fall Off"

17. "Kill a Man"

18. "Fall in the Fall"

19. "Simple Man"

20. "Save Me"

Contact Piet at (414) 223-5162 or plevy@journalsentinel.com. Follow him on Twitter at @pietlevy or Facebook at facebook.com/PietLevyMJS.

This article originally appeared on Milwaukee Journal Sentinel: Jelly Roll moved to tears at sold-out Milwaukee show for 23,000 fans