Drake is one of hip hop’s most scrutinized figures, with his actions and social media activity frequently throwing fans and media into a frenzy. Recently, an innocuous Instagram move has rekindled old tensions between the Toronto rapper and tennis legend Serena Williams. What’s the fuss all about? Let’s dive in.

The trigger was a series of photos posted by Drake on his Instagram, where he was seen with rapper Sexyy Red. Captions and poses aside, it was an interaction under the post that grabbed everyone’s attention. A fan commented, “Serena Williams upgrade,” in reference to Sexyy Red, a remark that Drake liked, setting off a storm of speculation and controversy.

To understand the weight of this seemingly benign action, we need to revisit the history between Drake and Serena Williams. Their relationship dates back to the mid-2010s, with rumors swirling about a romance that captivated both entertainment and sports media. Although both have moved on, the entanglement remains a talking point among fans and gossip columns alike.

In 2022, Drake’s track “Middle of the Ocean” sparked further intrigue. In it, he subtly dissed Williams’ husband, Alexis Ohanian, calling him a “groupie” and questioning the sincerity of their civil rapport. The diss track came after years of speculation about Drake’s lingering sentiments towards Serena, often fanned by cultural events and media narratives.

The recent Instagram episode has added another layer to this complex relationship. Some perceive it as mere playfulness typical of Drake’s public persona, while others see it as a calculated move to stir the pot. After all, Drake is no stranger to drama and frequently uses his massive platform to churn the rumor mill.

Serena, however, has shown resilience against such media flares, particularly focusing on her family and career. After Kendrick Lamar’s Super Bowl 2025 performance, where she appeared on stage—a moment she insists was a homage to her Compton roots—the spotlight turned on her with new vigor. Her husband, Alexis Ohanian, took to X (formerly Twitter) emphasizing the criticism Serena faced in the past for similar dance moves, hinting at a broader conversation about media biases and cultural criticisms.

View this post on Instagram

Drake’s apparent interest in nurturing his relationship with Sexyy Red at Serena’s comedic expense is, to some critics, old ground in new clothing. Whether this episode will trigger further back-and-forth is uncertain. But historically speaking, Serena tends to rise above, focusing on her legacy and the broader discourse around representation in sports and beyond.

As for the hip hop world, Drake’s every move—be it on Instagram or in a song—continues to serve as a topic of intrigue and analysis. His ability to weave personal narratives with broader cultural commentaries is part of the allure that keeps fans engaged. Yet, this latest interaction is a reminder that under the celebrity gloss, real people with complex histories often lurk, waiting to be dissected under the public gaze.

For audiences and fans, this situation is reflective not just of pop culture’s tendency to favor drama, but also a reminder of how personalities can use their art and influence as a form of ongoing dialogue. Whether Serena Williams will choose to respond directly or not, this latest Instagram interaction is sure to fuel conversations both in hip hop and beyond for weeks to come.