The Shady Truth: 5 Controversial Things Drake Has Said (Or Done) About Serena Williams

The complicated, on-again, off-again relationship between hip-hop superstar Drake and tennis legend Serena Williams has been a source of fascination for over a decade, but the conversation has recently been reignited with fresh controversy and shocking revelations. As of December 18, 2025, Drake has once again put his past with Williams in the spotlight, not through a direct statement, but through a calculated social media action and the unearthing of old studio footage, proving that the tension is far from over.

The saga, which began with dating rumors in 2011, continues to generate headlines, blending world-class sports with rap beef and celebrity drama. From cryptic song lyrics to undeniable social media shade, here is a deep dive into the most controversial and telling things Drake has said—or done—about Serena Williams.

Serena Williams and Drake: A Brief History of Their Entangled Lives

To understand the depth of Drake's comments, it is essential to first grasp the timeline of their connection, which spans multiple years and major life events for both global icons.

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• Drake's Full Name: Aubrey Drake Graham
• Born: October 24, 1986, in Toronto, Canada
• Occupation: Rapper, Singer, Songwriter, Actor, Entrepreneur
• Key Albums: Take Care, Nothing Was the Same, Views, Scorpion, Her Loss

• Serena Williams' Full Name: Serena Jameka Williams
• Born: September 26, 1981, in Saginaw, Michigan, USA
• Occupation: Professional Tennis Player (Retired), Entrepreneur, Investor
• Key Achievements: 23 Grand Slam Singles Titles, 4 Olympic Gold Medals, former World No. 1

The pair were first romantically linked around 2011, with rumors of a casual dating relationship persisting for years. The most public phase of their romance occurred in 2015, when they were frequently seen together, including a widely publicized moment where they were allegedly kissing at a Cincinnati restaurant. The relationship reportedly cooled down before Williams began dating and eventually married Reddit co-founder Alexis Ohanian in 2017, with whom she shares two children, Olympia and Adira.

1. The 2024 'Too Good' Confession: A Long-Buried Love Song Revealed

One of the biggest and most recent bombshells came in early 2024, years after their public romantic link had faded. Through a collection of archival footage and unreleased content launched on his website, Drake finally confirmed the inspiration behind one of his most popular songs: "Too Good," his 2016 collaboration with Rihanna.

The Lyrics That Were Always About Her

In the newly released studio footage, Drake is seen admitting that the track, which features lyrics about a love being taken "for granted," was directly inspired by his relationship with the tennis superstar.

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• The Song: "Too Good" (from the 2016 album Views)
• The Key Line: "I’m way too good to you, you take my love for granted / I just don’t understand it."
• The Revelation: Drake confessed the emotional core of the song—the feeling of being underappreciated—was a direct reflection of his dynamic with Williams during their time together.

This revelation provides a deep, emotional context to their history, suggesting that while their public appearances were fleeting, the connection was significant enough to inspire a major hit song on one of his most successful albums. It was a private moment that became public years later, offering fans a definitive answer to a long-standing celebrity mystery.

2. The 'Serena Williams Upgrade' Instagram Shade

In a move that sparked immediate and widespread controversy in late 2023 and into 2024, Drake was accused of throwing subtle shade at his ex-flame via a social media post. The incident occurred when the "Hotline Bling" rapper posted photos of himself playing tennis with rising hip-hop artist Sexyy Red.

The 'Like' That Launched a Thousand Headlines

The drama wasn't in the photo itself, but in the comments section. A fan posted a comment that read, "Serena Williams upgrade," suggesting that Sexyy Red was an improvement over the legendary athlete. Drake, whose social media activity is constantly scrutinized, publicly hit the "like" button on the comment.

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This simple act of liking a comment was immediately interpreted by fans and media outlets as a deliberate, albeit subtle, jab at Williams. It reignited the long-dormant feud and led to speculation that there was still lingering resentment or tension between the two celebrities. The timing was also noted by some, as it came after Williams had made a cameo in a Super Bowl halftime performance by Drake's rival, Kendrick Lamar, adding another layer of complexity to the perceived diss.

3. The Cocky Sports Reference in 'Worst Behavior'

Long before the Instagram drama and the "Too Good" reveal, Drake was already referencing Serena Williams in his music, establishing her as a figure in his lyrical landscape. The most famous example comes from his 2013 track "Worst Behavior."

The Tennis Match Challenge

In this song, Drake boasts about his lavish lifestyle and connections, including a very specific reference to the tennis GOAT.

• The Song: "Worst Behavior" (from the 2013 album Nothing Was the Same)
• The Lyrics: "I'm with my whole set, tennis matches at the crib / I swear I could beat Serena when she playin' with her left."

While some saw this as a playful nod to a friend, others viewed it as a characteristic Drake boast—a subtle attempt to diminish her status, even in a hypothetical scenario. The line suggests a level of intimacy ("tennis matches at the crib") that fueled dating rumors, but the competitive edge was undeniable. It was a classic example of a "backhanded compliment" that simultaneously confirms a close relationship while asserting his own dominance, even in her domain.

4. The 'Curse' Rumor That Followed Him

While not a direct quote, one of the most persistent narratives that emerged from Drake's association with Williams was the infamous "Drake Curse." This was a widespread, albeit humorous, fan theory that suggested any sports team or athlete Drake publicly supported or was romantically involved with would subsequently lose or underperform.

This rumor gained significant traction in 2015 when Drake was often seen courtside at Williams' matches. During this period, Williams was on a historic run, chasing a calendar-year Grand Slam. After their public sightings, she suffered a shocking loss at the US Open, which many fans jokingly—or seriously—attributed to the "curse."

Although Drake never directly commented on the 'curse' itself, his constant presence and the subsequent media frenzy surrounding her losses became a major point of discussion, effectively making his association with her a controversial topic in the sports world. This perception, fueled by his proximity to her professional life, was an indirect form of commentary on their relationship's impact.

5. The Unspoken Response to Her Marriage

When Serena Williams married Alexis Ohanian in 2017, the tennis world celebrated. Drake, however, remained publicly silent on the matter. His lack of a public statement was, in itself, a form of loaded commentary that spoke volumes to fans who had followed their relationship history. While a celebrity is under no obligation to comment on an ex's marriage, the silence was interpreted by many as a sign of lingering feelings or, at the very least, a desire to distance himself from the narrative.

In the years since, Williams has repeatedly denied any animosity, stating that she and Drake have a mutual respect and that the media often sensationalizes their interactions. However, Drake's actions, particularly the recent Instagram "like" and the "Too Good" reveal, suggest that the chapter is not entirely closed for him. The rapper continues to use their shared history as material, whether in archival footage, song lyrics, or subtle social media gestures, ensuring that the question of "what did Drake say about Serena Williams" remains an ever-evolving answer.

The latest developments—the confirmation of an emotional love song and the public approval of a shady comment—cement the fact that the dynamic between Drake and Serena Williams is one of the most enduring and complex celebrity relationships in modern pop culture, one that Drake seems determined to keep in the public eye.