Serena Williams & Drake: Unpacking Their Complex History Amidst Current Music Feuds

While their romance was never fully confirmed by either party, the whispers and public sightings of tennis legend Serena Williams and hip-hop superstar Drake captivated fans for years. Their relationship, though brief and enigmatic, continues to resurface in the cultural consciousness, most recently fueled by the intense lyrical battles dominating the music world. This article delves into their intricate past, explores recent developments involving Kendrick Lamar, and examines the lingering impact of their connection on all parties involved.

The current music landscape has been electrified by the highly publicized feud between Drake and Kendrick Lamar. Lamar’s recent music video for “Not Like Us” has become an undeniable cultural phenomenon, with its biting lyrical and visual disses aimed squarely at Drake. The track has resonated deeply, seemingly even with Serena Williams herself. The acronym ‘O.V.O.’ (October’s Very Own), often associated with Drake, has been symbolically challenged, and it appears the tennis icon is in full agreement that Lamar’s track, brimming with pointed critiques of her former ‘fan’ (and rumored flame), is poised to be “the hit of the summer.”

At a recent panel discussion held at the prestigious ESSENCE Festival of Culture in New Orleans, the formidable 42-year-old tennis trailblazer made her feelings about the diss track abundantly clear. When directly questioned about the song that has sent shockwaves through the music industry, Williams, known for her candidness on and off the court, wasted no time in communicating her strong appreciation for it.

“I love that song. It’s like the hit of the summer. When they play that jam, I’m jamming,” Williams enthusiastically declared. She further emphasized her enjoyment, stating, “That jam is jamming.” Her unreserved endorsement quickly went viral, adding another fascinating layer to the already complex narrative surrounding Drake’s public persona and past relationships. For many, her approval felt like a significant moment, given her unconfirmed yet widely speculated romantic history with the Canadian rapper.

Serena Williams co-signs “Not Like Us” by Kendrick Lamar pic.twitter.com/hBSe2wrK9t

— Complex Music (@ComplexMusic) July 7, 2024

Williams, who hails from Compton, California, much like Kendrick Lamar himself, expressed admiration for the track’s authenticity and visual elements. “You definitely Crip walking in that song. It’s so cool what he did though. Bringing everyone to the stage? That was incredible … I couldn’t believe it,” Williams elaborated, referencing the powerful live performance of “Not Like Us” where Lamar united numerous West Coast artists on stage, a moment that quickly became iconic. Her appreciation for the cultural statement Lamar made, particularly as someone deeply rooted in the same community, underscored the song’s profound impact beyond just the lyrical jabs.

While the precise nature of the relationship between Williams and Drake was never officially confirmed, making it difficult to pinpoint an exact end, various public interactions and lyrical references over the years offered tantalizing clues. It seems apparent that the “Teenage Fever” rapper harbored strong feelings, feelings that perhaps resurfaced in his collaborative album “Her Loss” with 21 Savage. On this album, Drake included a notable and overt dig at Williams’ husband, Alexis Ohanian, the co-founder of Reddit, bringing their personal lives into the lyrical spotlight.

The specific lines that ignited a public stir were found in Drake’s solo track, “Middle Of The Ocean,” where he rapped: “Sidebar, Serena, your husband a groupie / He claim we don’t got a problem but / No, boo, it is, like you comin’ for sushi / We might pop up on ’em at will like Suzuki.” This provocative lyric was widely interpreted as a disrespectful jab at Ohanian, not only questioning his public support for his wife but also insinuating an ongoing tension between Drake and Serena’s family life. The reference to Ohanian as a “groupie” was particularly cutting, aiming to diminish his stature and devotion.

The reason I stay winning is because I’m relentless about being the absolute best at whatever I do — including being the best groupie for my wife & daughter. pic.twitter.com/oaEKuRWFnj

— Alexis Ohanian 🇦🇲 (@alexisohanian) November 4, 2022

In a masterful display of turning a perceived insult into a powerful affirmation, Alexis Ohanian responded to Drake’s lyrical attack on X (formerly Twitter). He posted, “The reason I stay winning is because I’m relentless about being the absolute best at whatever I do — including being the best groupie for my wife & daughter.” Ohanian’s retort brilliantly recontextualized the term “groupie,” transforming it from an intended slight into a badge of honor, emphasizing his unwavering support and adoration for his family. This response was widely lauded by fans and commentators alike, seen as a dignified and loving counter to Drake’s seemingly bitter remark, effectively silencing further speculation and redirecting the narrative back to his familial devotion.

Possible Timeline of Serena Williams & Drake’s Connection

The relationship between Serena Williams and Drake, while never explicitly confirmed as exclusive dating, began to draw public attention as early as 2011. Drake’s presence at her matches became a recurring theme, fueling speculation and leading to playful (and sometimes provocative) social media interactions. This timeline outlines the key moments that defined their intriguing, on-again, off-again public connection:

• 2011: Early Flirtations and Public Appearances
  Drake was first publicly recorded attending Serena’s tennis matches, showing up courtside at various tournaments. His interest wasn’t just physical presence; he even hinted at their evolving relationship on Twitter. In a now-famous tweet, he playfully wrote, “@serenawilliams I cannot wait to put it on you and make you sweat……….during our match this weekend.” This tweet, suggestive and playful, immediately sparked rumors of a burgeoning romance, as fans and media outlets began to connect the dots between the celebrity athlete and the rising hip-hop star. Drake’s frequent attendance at her games, often positioned prominently, became a clear signal that something more than just a casual friendship was brewing.
• 2013: Lyrical References Emerge in Music
  Drake further solidified the public’s perception of their connection by name-dropping Williams in his music. On his track ‘Worst Behaviour’ from his critically acclaimed album ‘Nothing Was the Same,’ he rapped, “I’m with my whole set / Tennis matches at the crib / I swear I could beat Serena when she playin’ with her left.” These lyrics were a clear nod to their personal interactions, suggesting a familiarity that went beyond public appearances. The reference to “tennis matches at the crib” painted a picture of intimate, private moments, reinforcing the idea of a close, perhaps romantic, bond.
• 2015: The Common Feud & Public Sightings Intensify
  The period around 2015 saw an increase in the public’s focus on Drake and Serena, partly due to his well-documented feud with fellow rapper Common. Common, who had previously dated Williams from 2007 to 2010, later admitted that his lyrical exchange with Drake was, “Unfortunately the war might have been over a girl, even though at the time I never said that.” This admission strongly implied that Serena was at the heart of their rivalry, further cementing the perception of a romantic link between her and Drake. The public sightings also became more frequent and suggestive. There were two widely circulated alleged videos online: one reportedly showing them making out in a Cincinnati restaurant, and another capturing them leaving a venue together to get into a car. These instances, though unconfirmed by the stars themselves, added significant fuel to the dating rumors, portraying a relationship that was moving beyond casual friendship.
• Continued Support and Eventual Divergence
  Drake continued to be spotted at Serena’s tennis games over the subsequent years, demonstrating consistent support for her career. His presence at major tournaments, including Wimbledon 2018, was often highlighted by the media, keeping the speculation alive even as their individual lives began to take different paths. This ongoing presence, even if just as a friend or admirer, underscored the deep-seated connection they shared, regardless of its romantic status.
• 2017: Serena’s Marriage and Family Life
  The narrative took a definitive turn when Williams married Alexis Ohanian in a lavish ceremony in 2017. Later that same year, the couple welcomed their first child, a daughter named Alexis Olympia Ohanian Jr. Serena’s marriage and the subsequent birth of her daughter marked a clear and happy progression into a new chapter of her life, effectively bringing an end to any lingering speculation about a romantic future with Drake. While Drake’s public appearances at her matches continued for a time after this, the nature of their interaction visibly shifted, transitioning into what appeared to be a platonic, supportive friendship, rather than a budding romance.

The intricate dance between celebrity relationships, public speculation, and artistic expression is vividly showcased in the story of Serena Williams and Drake. What began as a rumored romance evolved into a complex narrative, punctuated by lyrical disses, social media responses, and a lingering public fascination. Serena’s recent enthusiastic embrace of Kendrick Lamar’s diss track against Drake serves as a powerful reminder that even years later, the echoes of past celebrity connections can still reverberate through the realms of music, sports, and popular culture, offering continuous fodder for public discussion and intrigue.