The Shady Truth: 5 Times Drake’s Comments About Serena Williams Caused Major Drama (Latest 2024 Update)
The complicated and often controversial relationship between global superstar Drake and tennis legend Serena Williams has once again flared into public view, proving that their decade-long history is far from over. As of late 2024, new drama—fueled by an unexpected Instagram like and a high-profile clapback—has reignited the speculation about their past rumored romance and current tension.
This article dives deep into the most significant and often cryptic things Drake has said or done regarding Williams, from veiled song lyrics to explicit social media shade, providing a fresh, up-to-date look at one of pop culture's most enduring and fascinating feuds.
Drake and Serena Williams: A Biography and Relationship Timeline
The history between Aubrey "Drake" Graham and Serena Williams is a complex tapestry of rumored romance, public support, and lyrical jabs. Their interactions span over a decade, starting long before Williams married tech entrepreneur Alexis Ohanian.
- Drake's Full Name: Aubrey Drake Graham
- Drake's Birth Date: October 24, 1986 (Age 39 as of late 2025)
- Drake's Occupation: Rapper, Singer, Songwriter, Actor, Entrepreneur
- Serena Williams' Full Name: Serena Jameka Williams
- Serena Williams' Birth Date: September 26, 1981 (Age 44 as of late 2025)
- Serena Williams' Occupation: Professional Tennis Player (Retired), Entrepreneur, Investor
- Rumored Romance Timeline: The two were first linked in 2011 and were rumored to have dated on and off until 2015. Drake was often seen courtside at her matches, fueling the speculation.
- Current Status: Williams is married to Alexis Ohanian (since 2017), with two children. Drake remains unmarried, but their "beef" continues to surface in his music and social media activity.
The 5 Most Explosive Things Drake Has Said or Done About Serena Williams
While their relationship began with mutual admiration and rumored dating, it has since devolved into a series of highly publicized snubs and lyrical shots. Here are the most notable instances of what Drake has said about the tennis GOAT.
1. The 2024 "Serena Williams Upgrade" Instagram Shade
The most recent incident that brought their relationship back into the spotlight occurred in 2024. Drake, who had been collaborating with rapper Sexyy Red, posted a photo of her on his Instagram. The drama peaked when he was caught liking a highly controversial comment on the post.
The comment, which quickly went viral, referred to Sexyy Red as a "Serena Williams upgrade." By liking the comment, Drake appeared to endorse the sentiment, reigniting the long-standing fan speculation about his past with Williams and sparking renewed "beef" rumors. This subtle yet public act of shade was seen by many fans as a deliberate jab at the legendary athlete.
2. The Infamous "Worst Behavior" Tennis Diss
Years before the Instagram drama, Drake made a direct, competitive reference to Williams in his 2013 song "Worst Behavior," from the album Nothing Was the Same. The lyric was a playful, yet bold, boast that set the tone for their future interactions.
The line in question is: "I'm with my whole set, tennis matches at the crib. I swear I could beat Serena when she playin' with her left." This lyric, which claims he could defeat one of the greatest athletes of all time even with her non-dominant hand, was interpreted by some as a playful challenge and by others as a slight underestimation of her power and skill. It solidified their connection in pop culture history, tying her name to his discography.
3. Calling Serena's Husband a "Groupie" in "Middle of the Ocean"
Perhaps the most direct and aggressive comment came in 2022 on the track "Middle of the Ocean." By this time, Serena Williams was happily married to Reddit co-founder Alexis Ohanian. Drake used the song to take a shot not at Serena, but at her husband.
The controversial lyric is: "Sidebar, Serena, your husband a groupie / He claim we don't got a problem but / No boo, it is like you coming for sushi." This line caused immediate backlash, painting Ohanian as an opportunist or a follower. Ohanian quickly responded on social media, implying that Drake was irrelevant and that he was too busy building a legacy with his family to care about the rapper's comments.
4. The Secret Meaning Behind "Too Good"
Not all of Drake's references were antagonistic. In a rare moment of revelation, Drake confirmed in a never-before-heard snippet that his hit song "Too Good," featuring Rihanna, was actually written about Serena Williams.
The song, released in 2016, is about a relationship where both parties feel they are "too good" for the other person to be playing games. This revelation provided a window into the genuine emotional complexity of their rumored romance, suggesting that their breakup was perhaps a mutual feeling of being mistreated or undervalued, rather than a one-sided affair.
5. The 2011 Tweet That Started it All
The very first public comment from Drake about Williams dates back to 2011, long before the major hits and the public drama. It was a simple, flirtatious tweet that first sparked the rumors of a relationship.
Drake tweeted: "@serenawilliams I cannot wait to put it on you and make you sweat as much as possible." This suggestive, playful comment on social media was the initial spark that led to years of speculation, courtside appearances, and, eventually, the lyrical jabs that have defined their public history. It shows that the foundation of their connection was rooted in a strong, public attraction.
The Aftermath: Serena’s 2024 ESPY Awards Clapback
Serena Williams, known for her composure and focus, rarely addresses the drama directly. However, she delivered a powerful, non-verbal clapback to Drake's ongoing antics at the 2024 ESPY Awards.
During the ceremony, Williams was seen dancing enthusiastically to Kendrick Lamar's track "Not Like Us"—a song that is widely recognized as a scathing diss track aimed directly at Drake. By choosing to publicly celebrate and dance to Drake's rival's music on a highly visible stage, Williams sent a clear message to the rapper that she was unbothered by his shade and was willing to align herself with his opposition. This move was celebrated by fans as the ultimate power play and a definitive response to the continuous lyrical and social media jabs. This recent event confirms that the "beef" is still very much alive and remains a fascinating subplot in the careers of both global icons.
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