He has always been notably quiet in person and has seldom had a lot to say from stage.

But big speeches weren’t what people have wanted from Alan Jackson. They wanted the songs: “Drive (For Daddy Gene),” “Chattahoochee,” “Don’t Rock the Jukebox,” “Remember When,” “Small Town Southern Man,” “Where Were You (When the World Stopped Turning).” Those titles spoke volumes about Jackson as a singer-songwriter, and about the fans he served.

Jackson caps his concert career Saturday (June 27) at Nashville’s Nissan Stadium with Last Call: One More for the Road — The Finale, a show that serves as a milestone in the Country Music Hall of Fame member’s career and a nostalgic reminder of his substantial body of work. But just as importantly, it highlights his influence. More than 35 years after Jackson reached the national spotlight, the ‘90s country that he helped define — marked by strong hooks, proud lower- and middle-class stories and an unapologetic use of fiddle and steel guitar — is hot. “Last Call” will feature appearances by a bundle of younger artists who took the baton, including Riley Green, Cody Johnson, Lainey Wilson, Eric Church, Miranda Lambert, Lee Ann Womack and Luke Combs, just to name a few.

They’re not the only music folks who’ll be on hand. The stadium will also welcome the four executives who headed the labels that oversaw his releases prior to this year: Tim DuBois, who signed Jackson to Arista Nashville; Joe Galante, who worked with him when a restructuring placed Arista under the RCA Label Group umbrella and, later, under Sony BMG; Mike Dungan, who signed him to Capitol Nashville; and Cindy Mabe, who succeeded Dungan at Universal Music Group Nashville (now MCA).

They collectively see Jackson as a key voice for the nation’s heartland.

“I call him the Norman Rockwell of country music,” DuBois says. “He just paints a picture that is so relatable to middle-class America.”

Jackson has amassed 26 No. 1 singles on Billboard’s Hot Country Songs among 50 top 10 singles, deftly using everyday language and unpretentious musical construction to create a bond with the genre’s listeners. He avoided gimmickry and never overplayed the emotional content in his material. Instead, he delivered his stories with sincerity and respect, using those tales as his primary means of communication. He could acknowledge commitment and economics in the same chorus — as he did when he sang “Livin’ on love, buyin’ on time” — capture intimacy in the lines of “When Somebody Loves You” and laugh at rejection in “She’s Got the Rhythm (And I Got the Blues),” the latter co-written with fellow traditionalist Randy Travis.

Jackson connected with men and women at the heart of their humanity, but he had his surface attractions, too.

“I know I sold a ton of music,” DuBois quips, “but I also sold a lot of long legs and long hair.”

A native of Newnan, Ga., Jackson communicated regular-Joe status through a love for the water and a passion for automobiles. He married his high-school sweetheart and kept cassette recordings of his songs in brown paper grocery bags, writing about his parents, his wife, his good times, his church and his growing pains. Fans saw him as one of their own — and he was. He still is.

But he wasn’t a pushover when it came to the music business. He needed a record company, but wasn’t about to sacrifice his identity to make it. Particularly as a younger man, he was prone to push back when the business people asked him to try marketing moves that didn’t fit his view of his art.

“He wanted it to be about the music,” remembers Dungan, who first worked with Jackson in the early days of his career. “When you’re the head of marketing, as I was at Arista, there are a million opportunities to fight with a man like that.”

And they did. Dungan remembers one brutally loud argument at a Nashville restaurant that turned the heads of other patrons. It wasn’t personal. Jackson simply had a public profile and — like most great artists — a sense of what he was willing to do when his name or likeness was attached. He knew what made his business work, and he didn’t compromise when it didn’t make sense.

“He was always on the lookout for anyone and everyone who was going to try to interfere with his creative process,” Dungan recalls.

Galante knew that side of Jackson, too. A year before Arista came under Galante’s leadership, Jackson registered a top 5 single with “Little Man,” a frank lament about the brute force of big businesses gobbling up market share in small communities. It wasn’t just posturing, but his own artistic success placed him in situations where he had to make choices between the music and the business sides of the music business.

When WHTZ New York, Z100, heard Jackson’s 9/11 reflection, “Where Were You (When the World Stopped Turning),” the top 40 station was interested in playing it. As a five-minute country ballad, “Where Were You” was a bit of an outlier for a pop station. The company was willing to accept that, but executive vp Butch Waugh funneled one request to Galante: Could Jackson remix it with less steel guitar? Galante called the artist with the proposal.

“The silence — it seemed like an eternity, but it was probably three or four seconds,” Galante recalls. “He said to me, ‘I kind of like steel.’ And the next thing I heard was a click. I went into Butch’s office, and he said to me, ‘How did it go?’ I said, ‘Well, as I expected, he’s not going to change the record. And I don’t think he should.’”

It’s not like Jackson was acting out of selfishness. Though his songwriting was a hallmark of his career, he recorded a fair number of outside songs, including 18 of his top 10 singles, such as “Little Bitty,” “It’s Five O’Clock Somewhere,” “Gone Country” and “Right on the Money.”

There was a practicality about it — invariably, the songs represented his love of classic country or expressed his viewpoint in a way that he didn’t think he could. The songs he selected and the compromises he refused to make were all a part of a genre that was central to his identity.

“He never lost his roots, and I think he always thought about that,” Galante says. “I mean, he was a shade-tree mechanic, coming from a small town, and still remembered what the struggle was like. I think that resonated in everything he picked, or wrote, and we worked.”

When Jackson left Arista, he called Dungan, who had moved on to Capitol, and suggested working together again. He acknowledged that they had had their share of arguments, but said he always knew that Dungan was giving him an honest assessment. He apologized for the long-ago restaurant squabble, and he laughed it off when Dungan said he wanted to get Jackson back on the radio. Jackson believed programmers had moved on.

“I was very shocked, because if you ever work with artists, you know none of them ever say that,” Dungan notes. “It’s the other side of the coin. It’s like they will not accept that radio won’t play them anymore. Here was a guy, who was very difficult in his early career, being the most grown-up adult in the room.”

The fact is that Jackson had a handle on what worked for him.

“Looking back,” says DuBois, acknowledging his own battles with Jackson, “he was right more times than I was.”

Jackson’s final concert is timely in a way he could not have predicted when he booked it more than a year ago. Back in 1989, Jackson — despite his longing for a recording contract — insisted on meeting DuBois’ boss, Clive Davis, before he became the first artist signed to Arista’s unproven Nashville division. Davis died on June 22, just five days prior to Jackson’s stadium show. Similarly, Larry Shell, who co-wrote “Murder on Music Row” — the award-winning 1999 release that excoriated the country industry for turning its back on tradition — died June 17. George Strait, who recorded “Murder” with Jackson, will participate in the concert.

Jackson’s legacy “matters so much, because the past, present and future of country music all connect together,” says Mabe, whose Joan of Arc Music is set to develop an NBC special out of the concert. “He’s an extension of Hank Williams, and what he’ll do for that next generation is they’re going to pick up the extension of Alan Jackson and move it forward. That’s why this concert and everything that comes in this moment is going to be so pivotal. It’s a cultural moment. It’s not just a last concert.”

Mabe’s production, of course, will need to demonstrate that through the music and through the other voices that might appear in it. Jackson, as someone who isn’t prone to talk much publicly, is certainly not one to boast. It’s not necessary.

The most talkative people in a room “tell you everything that they possibly know about anything,” Mabe observes. “The one with all the information is the quiet guy in the corner. That’s Alan Jackson. I’ll be honest, he knows a lot of stuff.”

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Matt Damon is stepping into the studio and behind the mic for… a rap track?

That’s the premise for a new clip for Water.org, helping to promote the charity’s new “Get Blue” initiative. In a clip posted to Instagram earlier this month, Damon debuts his rap alter ego, “The Nomad,” to riff on the “constant struggle” to get water into the homes of those who need it most. The actor-turned-aspiring musician seeks advice from Hit-Boy, the Grammy-winning producer, who questions whether rapping is really the right move for Damon’s altruistic intentions.

“Isn’t ‘Nomad’ just ‘Damon’ spelled backwards?” Hit-Boy asks, to the chagrin of the embarrassed actor.

In person, Damon is anything but embarrassed to promote the Get Blue campaign, no matter what it takes.

“We’re always looking for ways to cut through all the noise, and sometimes, humor is a shortcut to get people’s attention,” he tells Billboard. “We’ll try anything, you know?”

Damon hasn’t had to rap in his career to date, though he notes that, “I sang in The Talented Mr. Ripley a long time ago and uh, I sung in Eurotrip.”

And while his kids are musically-inclined — “Taylor [Swift] is a huge influence in our house,” he says. “We know that catalog pretty well” — don’t expect to see Damon debuting any official musical endeavors anytime soon. “Obviously, Kendrick has nothing to worry about. I’m not gonna become a rapper,” Damon says. “I don’t think that would go well.”

For now, Damon’s rap attempt will just live on social media, with the actor also using his studio time in the clip to tell Hit-Boy about the millions of people around the world who still lack access to clean water. With the Get Blue campaign, Water.org is partnering with brands like Gap, Starbucks and Amazon, to launch products that give back. For every purchase of a Get Blue product on the Gap site, on Amazon’s Get Blue storefront (official page coming in July), or a purchase of two specialty drinks on Starbucks (the Iced Blue Coconut Matcha and the Blue Coconut Refresher), the brands will make a donation to Water.org.

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Amazon makes it even easier, with a dedicated Get Blue playlist for inspiration and a host of REDISCOVER playlists on Amazon Music, bringing back popular artists and songs in one place. Amazon says it will donate $1 to Water.org every time someone plays a participating artist’s REDISCOVER playlist. The exact list of artists will be announced in July.

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An even easier way to make a difference: customers with an Alexa-enabled device can say, “Alexa, donate to Get Blue” and Amazon will contribute $5 on their behalf.

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While much movement has been made to increase access to water and improve safe drinking conditions around the world, Damon notes that more than two billion people still lack access to safe water — that’s one in four people globally.

“It’s so hard for us to relate to growing up here,” Damon says. “You’re only a few steps away from a clean drink of water, whereas if you think about AIDS or cancer or things like that, usually there’s an emotional connection for somebody. You’re never very many degrees removed from somebody who’s struggling with that, whether it’s a family member or a friend.”

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“What this [campaign] does,” he explains, “is it raises the awareness, and then hopefully, we can start this larger cultural conversation, and it’ll stay at the front of people’s minds.”

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The Get Blue campaign continues the work that Gary White has been doing for decades, as the CEO and co-founder of Water.org. The charity works with local partners on the ground to offer small, affordable loans so families can get the pipes, pumps, or plumbing they need to serve safe drinking water at home. Education is also an important of their advocacy, with White noting that many young children in developing countries can’t attend school, because they are in charge of water collection for their families.

“So many people around the world, when they wake up tonight, they don’t know where they’re going to get their water, and they have to spend time and sometimes money just to get it,” White tells Billboard. “And with Water.org, we’ve pioneered some really innovative ways to kind of close that gap,” he says, noting the organization’s work in everything from building wells to facilitating clean sanitation.

“But what we also realize is we need to bring in a wider audience,” White adds. “It’s critically important that we have these partners who have a platform, who have a voice, who know how to connect through cool shirts or music, because that’s where people live.”

White’s goal for the campaign and for his organization: “We’ve reached over 90 million people with our water programs and I think in the next four years, we can reach another 100 million.”

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Whether you’re ordering a fancy “blue” Starbucks drink or picking up a T-shirt at Gap, Damon says the Get Blue campaign makes it easier than ever to make a difference.

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“When I was growing up, on our refrigerator, my mother had this quote from Gandhi, and it said, ‘No matter how insignificant what you do may seem, it is most important that you do it,’” he says. “And I’ve always thought about that. I think the problems of the world can feel overwhelming,” he continues, “but if everybody does their part, what you’re doing is not insignificant, because you’re going to save somebody’s life. You’re going to completely change the outcome of their life. And there’s nothing insignificant about that.”

Who knew Vice President JD Vance had Diddy jokes up his sleeve?

Vance visited the Richard Nixon Presidential Library to promote his memoir Communion: Finding My Way Back to Faith and was asked about a chapter that just so happens to be named “More Money, More Problems,”one of the late Notorious B.I.G.’s most popular songs. That’s when he quipped about the song’s producer, Diddy, being a “great Christian theologian,” before saying he’s “going to get in trouble” for the remark.

“I’m a millennial, and so I believe that’s the wisdom of the great Christian theologian P. Diddy, who as we found out in the last couple of years is very much not a Christian or a theologian,” the vice president joked about the embattled mogul after being asked why more money causes more problems. “I’m going to get in trouble for all kinds of things. That will be one of them. That will be in an attack ad at some point in the future.”

Diddy was sentenced to four years in prison last October on prostitution charges and is currently in the middle of appealing his sentence, which can take up to a year to be sorted.

Earlier this year, President Donald Trump revealed that Diddy asked him to consider a pardon through a handwritten letter. However, he said Puff’s criticism of him during his first run for president in 2016 “makes it more difficult to do,” even though the two have been cordial over the years.

Billboard has reached out to the White House for comment.

This week, Billboard’s New Music Friday Guide: Latin roundup — curated with key recommendations by Billboard Latin and Billboard Español editors — features a number of new songs and albums, including Bizarrap and Myke Towers’ “BZRP Music Session #42/66,” Becky G’s “Patrona” and Kane Rodriguez’s album Loco Soñador.

Released Wednesday, Argentinian producer Bizarrap dropped his latest music session featuring Puerto Rican artist Myke Towers. “BZRP Music Session #42/66” is the producer’s first session of the year. His previous one, “BZRP Music Session #0/66,” dropped in late 2025 and featured another Puerto Rican music icon, Daddy Yankee.

The music session with Towers was released in two different acts. In the first one, Towers’ signature melodic rapping style takes precedence while Bizarrap’s bass-heavy, hip-hop-driven beats deliver the undertone. Through the lyrics, the rapper pays homage to his roots, rapping about his elevated lifestyle while making it clear that Puerto Rico remains on his mind no matter where his career takes him.

In the second part of the collaboration comes “Boobytrap,” a long-awaited track that fans have anticipated ever since an early snippet surfaced years ago. In the trap-leaning rap song, Towers shows off his lyrical tenacity, rapping about his lifestyle and how he now has the respect he didn’t get before from others in the industry. The song title “Boobytrap” refers to a famous strip club in Miami, also named Boobytrap, which the artist claims to visit whenever in South Florida.

Meanwhile, artists such as Hermanos Espinoza, Kane Rodriguez, Fuerza Régida and Mariangela also dropped new music this week.

The most recent New Music Latin poll was topped by Feid’s El Moco Verde with more than 49.53% of the vote. Which release this week do you think is best? Give these new releases a spin and vote for your favorite new Latin music release below.

Editor’s Note: The results of the weekly New Music Latin poll will be posted if the poll generates more than 1,000 votes. This poll closes at 11 a.m. ET on Monday, June 29.