Jelly Roll, Drake, and other stars have been giving lucky fans gifts worth thousands of dollars. But has this generosity gone too far?

“Fly us out to Greece!”

“Help my bf buy me an engagement ring!”

The photo is so unsettling that many wondered if the image was doctored — an AI “gotcha” seemed less grim than the idea of concerts becoming begging battlegrounds.

But anyone who followed Drake’s recent Anita Max Win Tour in Australia witnessed the artist’s generosity streak. In Sydney, he gifted a couple $25,000 and a honeymoon after they got engaged at his show. He told a Brisbane concertgoer that he would cover their mom’s cancer treatment after seeing a sign publicizing her illness. He gave another fan $20,000 after beating them in a round of rock paper scissors.

Over the years, these lavish handouts have become something of a Drake signature. His “God’s Plan” video, from 2018, shows him giving the nearly million-dollar production budget, supplied by his label, to people in need in Miami.

A few weeks ago, the rapper explained that he felt compelled to engage in these recent giveaways after a mother and daughter, who had attended one of his shows in 2024, were killed by a drunk driver when they left the venue.

“It really f—ked my mind up to think that we could go from having this much fun and then just like that, life changes,” he told the crowd at a Melbourne concert.

But such benevolence is complicated by social dynamics. The fan-artist relationship has always been transactional — an exchange of music for support, financial or otherwise. But the modern fan appears to want more. More access to an artist’s personal life. Additional tour dates. Longer shows. More albums. More input. More selfies in the street.

Now, they want more handouts. And they’re getting them from others, not just Drake.

At a March 17 concert at the Canada Life Centre in Winnipeg, American country singer Jelly Roll promised to pay off two audience members’ student loans after noticing signs the University of Manitoba students held up asking for help.

Last year, Nigerian American singer Davido donated $50,000 to a fan at his Madison Square Garden show. He had seen her sign asking him to “take (her) student loans away.”

Promoting his “Rich Slave” album, the late rapper Young Dolph announced that anyone who preordered his merch bundle would be entered into a contest to win a Lamborghini Aventador. (The winner later put it up for sale to buy a house.)

When a woman messaged GloRilla on Facebook asking for a $400 loan, the artist sent her $1,000.

“There’s a set of expectations that fans now bring that celebrities will own up to their class privilege,” said Michelle Cho, an assistant professor of East Asian popular cultures at the University of Toronto, whose research focuses on contemporary fandom and social media.

“It’s a very Oprah move,” she said of Drake’s handouts, referencing the American talk show host’s former penchant for giving expensive gifts to audience members. “‘You allow me to be a billionaire as long as I make the right gestures of still being able to relate to you and sympathize with you.’ But it’s complicated because it’s also a flex, so there’s a paradox built into it.”

In isolation, these are acts of kindness — temporary bridges over the widening gap between the haves and the have-nots. But collectively, these exchanges set disquieting expectations, devaluing art in the process. In the not-so-distant past, a fan wouldn’t have attended a concert hoping the performer might pay off their student loans or finance a bachelorette party to Ibiza. The music was enough. Now, one questions whether fans might be buying Drake concert tickets with the intention of entering a sort of ‘6 God’ lottery.

It speaks to the state of the economy that someone might think their best bet at paying off their mortgage is to hit up an artist. It speaks to the state of the music industry that artists are willing to write the cheque. Leave aside the irony of a fan spending hundreds of dollars on a Drake floor seat only to ask him to pay their vet bills. As we ready our handmade signs lamenting the state of our financial reality, perhaps we should think about whether we’re aiming them at the wrong people.

“It’s a relationship of weird benevolence but also captivation by the fans,” says Cho, “because the artist is trapped by them in a certain way.”

It’s an entitlement trap that some artists are trying to dismantle. Chappell Roan has made headlines for setting firm privacy boundaries with her followers. A few weeks ago, Jack White pushed back on “entitled” concertgoers who expected hours-long shows. Gracie Abrams recently spoke out after fans launched an online petition protesting her choice of support act.

These messages all seem to be grappling with one question: beyond the music, what does an artist really owe fans? With the costs of modern fandom rising, most notably through ticket and merchandise pricing, many will take every inch and dollar that they can get.

In some cases, they’re demanding what they feel they deserve.

“Fans are starting to become very aware of the role that they play in the attention economy, and are therefore looking for more recognition,” Cho said. “That’s what fans can leverage: ‘We can draw attention to you in ways that legacy media, and you yourself, cannot.’ Fans are positioned differently now because they can produce monetary value for an artist very quickly, so they hold the power in a way that they didn’t in the past.”

It has become more difficult than ever for artists to capture public attention, and with social media’s fickle shelf life, even more challenging to hold onto it. But as the fan-artist contract gets renegotiated, consider the message these tactics are sending music consumers.

Keith Jopling is a music strategist and host of “The Art of Longevity” podcast. After interviewing dozens of artists, including Norah Jones, Interpol and Nile Rodgers, about their decades-long careers, he sees these giveaway stunts leading artists, and their fandoms, farther away from what matters.

“You can dress it up and call it ‘artist experiences,’ but a fan’s engagement with the celebrity becomes more primary than the music. This is the ultimate mistake for artists and their representatives,” Jopling told the Star. “You’re putting more and more of yourself out there that isn’t music, so they are consuming you, but they aren’t necessarily consuming your music.”

Speak to any beneficiary of this largesse, however, and you can see how infectious this gift-giving can be. Newfoundland native Heather Sharpe, a long-time Drake fan, recently attended his concert in Perth, Australia, where she now lives. The tickets were a last-minute surprise from her partner, and she decided to bring a Canadian flag to wave at the Toronto rapper.

“I just wanted to represent back home,” Sharpe told the Star.

At one point during the show, Drake acknowledged his fellow Canadians.

“They’re from Newfoundland,” he told the crowd after briefly interacting with the couple. “Y’all probably don’t know where that is, but that’s back home.”

The artist then announced he would give them, along with a couple from Perth, $20,000 “to go wherever you want in the world.”

“I think I started to cry,” Sharpe said. “I was not expecting that at all. I’m still shocked.”

Sharpe, unlike her poster-wielding peers, had no expectation of going home thousands of dollars richer. But she was touched by the gesture.

“Yes, we 100 per cent go to these shows for the music, but it’s nice to show appreciation too,” she said. “Also, some people really do need it, right? I think everybody having signs is a bit much, but it’s still a beautiful thing that Drake is picking people out like that.”

Sharpe has yet to receive the money from Drake’s team, but she hopes to use it to fly her brother and mother over from Newfoundland.

When you hear a story like this, these giveaways could be seen as win-win scenarios for the artist. The stadiums are packed, folks go home happy, and the performer makes some feel-good headlines.

But in the interest of building artistic credibility and long-term relevance, is this a viable and sustainable approach?

For most artists, the answer is a resounding no. It’s hard enough to break even as a musician these days, let alone provide bonus incentives to sustain fan interest. And this is precisely why these collective shifts in fan expectation can be so damaging to the industry at large.

But even for the select few artists with bottomless pockets, the strategy is still flawed. It’s better to build a reputation for being kind than being cruel, but craft mustn’t lose its rightful place on the stage. As music continues to be devalued in an increasingly exploitative streaming era, artists and fans have to ensure that they aren’t contributing to the narrative.

“The irony is that the secret to longevity and maintaining your authenticity and dignity is to not be distracted from making the music,” Jopling said. “It can sometimes feel like people aren’t interested in the music anymore. But that’s not true. People are listening to music more than ever. So let’s not get distracted by the noise.”