After Drake debuted his Anita Max Wynn chain in December, he introduces the real-life Anita Max Wynn during his gambling livestream with Adin Ross on Sunday evening (April 13). The red-headed, voluptuous, glasses-wearing woman dropped in on Drake and Ross with shots early into the stream. Drake call on her often throughout the stream with drinks and when they execute "max" bets. "We'll let you know if we need you for a max wynn," Drake told Anita. The Anita Max Wynn chain did not make an appearance with the real-life person. The latest stream by Ross and Drizzy was announced on Saturday evening (April 12). Drizzy promised a million in bets for the livestream. Anita Max Wynn represents the tour Drizzy embarked on in Australia early 2025 that has been postponed to later in the year.
Drake’s Anita Max Wynn tour and his April 2025 livestream with Adin Ross showcase a deliberate pivot in his public persona. No longer confined to music, he’s reshaping his presence through spectacle, provocation, and platform dominance. At the center of this evolution is his high-profile alliance with crypto-betting giant Stake, which threads together his recent artistic and digital ventures. Launched in spring 2025, the Anita Max Wynn tour merged nightlife aesthetics with casino excess. The title—a sly pun on “I need to max win”—set the tone. Each concert unfolded like a high-stakes fantasy: slot machines whirled across massive LED screens, roulette wheels spun, and dice tumbled beneath pulsating lights. It was less a tour than a theatrical ode to gambling, repackaged as luxury escapism. The production design underscored a theme that’s defined Drake’s recent narrative—risk as both currency and performance.
More: More Drake On The Way: The Rapper Revealed New Album In The Works While Gambling With Adin Ross
Who Is Drake's Anita Max Wynn Girl
Ross emceed the event as Drake moved between casual banter and real-time wagers, maintaining a relaxed confidence throughout. Drizzy used the stream to reveal he is working on a new solo album. He didn't reveal any album title or release date, but shared that the album "slaps." The upcoming album will not collide with the rest of the AMW tour. The new dates for the delayed tour have not been announced yet.
$ome $exy $ongs 4 U, Drake and PartyNextDoor's joint album, continues to thrive on the Billboard charts. "Nokia" is racing to the top spot while the album quickly reaches platinum on the RIAA. Anita Max Wynn is an international tour presented by Live Nation.
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