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Rb Hip Hop

Drake Surprises Pregnant Fan With VIP Upgrade and Cash Giveaway at Sydney Show

"Are you 20 weeks pregnant? Get out of the pit. Get outta there," Drake told the fan.

Drake
Drake
Norman Wong

Drake’s Anita Max Win Tour in Australia continues to deliver viral moments—this time, with the rapper handing out $30,000 to a pregnant fan at his Sydney show at Qudos Bank Arena on Wednesday night (Feb. 19).

During a break in his set, Drake was scanning the crowd for signs when he spotted one that read: “I’m 20 weeks pregnant.” In a video circulating social media, the “Hotline Bling” rapper immediately reacted with disbelief.


“Are you 20 weeks pregnant? Get out of the pit. Get outta there,” Drake told the fan, later identified as Tiana Henderson, before instructing security to move her to VIP seating. “Give her some VIP tickets immediately and like $30,000,” he added before jokingly asking, “Who the f—brings a baby to a mosh pit?”

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Henderson and her friend were then escorted out of the packed general admission area to a more comfortable spot in VIP.

Drake’s latest giveaway is just one of many on his Anita Max Win Tour, where he has been handing out cash to fans throughout Australia. At his Melbourne show earlier this month, he reportedly gifted a fan $25,000 after noticing a sign referencing his son, Adonis, and another $20,000 to a concertgoer celebrating her birthday. While performing in Perth, he handed out $40,000 to two fans, including one waving the Canadian flag.

Earlier this week, he made headlines again by giving $30,000 to a fan in Sydney who held up a sign asking for help to quit their job at McDonald’s. The rapper played into the Australian slang, repeating the request in an exaggerated Aussie accent: “Help us quit Maccas, mate.”

In addition to his on-stage giveaways, Drake has been using the tour to promote $ome $exy $ongs 4 U, his newly released joint album with longtime collaborator PARTYNEXTDOOR, who has joined him on-stage during his Australian tour.

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Released on Feb. 14, the project has been a commercial success, earning over 56.6 million first-day streams on Spotify—making it the second-highest debut of the year. $ome $exy $ongs 4 U also broke the record for the biggest R&B/Soul album in Apple Music’s history by first-day streams worldwide.

Drake and Party are set to headline the first day of this year’s Wireless Festival in London with special guest Summer Walker in July. Drake will also headline the next two days with “The Mandem,” Burna Boy, and the Worl’ Boss Vybz Kartel by his side.

This article first appeared on Billboard U.S.

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Hilary Duff
Alfred Marroquin
Hilary Duff
Pop

Hilary Duff Reflects On Her Massive Lucky Me Tour: ‘I’m Really Proud of Myself, and That’s Hard to Feel As An Adult’

The current Billboard cover star received the Outstanding Pop Tour of the Year Award at the 2026 Billboard Live Music Summit in Los Angeles.

Current Billboard cover star Hilary Duff made an appearance at the Billboard Live Music Summit on Tuesday (Nov. 10) at the 1 Hotel West Hollywood to accept the award for Outstanding Pop Tour of the Year and talk about taking this run, The Lucky Me Tour, on the road.

Speaking with Billboard‘s executive editor Lyndsey Havens, Duff reflected on the moments when she decided that she wanted to tour behind her hit album luck… or something, a run that brought her back out on the road after an almost 20-year hiatus from touring.

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