Alerts & Newsletters

By providing your information, you agree to our Terms of Use and our Privacy Policy. We use vendors that may also process your information to help provide our services. This site is protected by reCAPTCHA Enterprise and the Google Privacy Policy and Terms of Service apply.

Drake, Serena Williams
Getty Images

The biggest diss on America’s biggest stage. Kendrick Lamar just made history as Super Bowl LIX, with the help of SZA, Samuel Jackson, and Serena Williams.

The rapper is on a victory lap after he won five Grammys for his song “Not Like Us.” Just a week after, he performed the song live, but not before teasing the audience. “I want to play their favorite song, but you know they love to sue,” likely referring to Drake‘s lawsuit against his own record label Universal Music Group and Spotify alleging defamation and inflating streams about K.Dot’s diss track against him.

Related: Serena Williams’ Net Worth Reveals How Much She Made From Tennis Before Her Retirement

In a surprise appearance, Kendrick brought along fellow Compton native Serena Williams out on stage, and she danced along to “Not Like Us.” Was there history between her and the “Hotline Bling” rapper?

Did Serena Williams date Drake?

Yes, Serena Williams did date Drake in 2011. He made a nod that his single “Too Good” was written for her. “I get heavy on a couple joints, but this is more about me and Serena,” Drake said of the track during a studio session, which featured Rihanna and was included on his fourth studio album, Views.

“It’s funny because when I make songs about women, I also make songs for them. So, I know what kind of song to make,” he continued. “If I’m gonna talk about them, I’ll at least do them the justice of making them a song that they like. So, I know Serena very well and I know that she’ll hear it loud and clear, but she’ll also not hate me for it because it’s lighthearted.”

The GOAT of tennis is married to Reddit founder Alexis Ohanian and the two share a daughter. Williams wasn’t the only person on that stage that Drake dated. SZA briefly dated Drake in 2009. She told Rolling Stone for a 2023 cover story, “[We] were really young. It wasn’t hot and heavy or anything. It was like youth vibes. It was so childish,” and even addressed whether Drake was a bad kisser in an episode of Hot Ones Versus, even if she didn’t actually give an answer. “We were children!” SZA said. “We were children — 2009, we were children” she responded to Keke Palmer saying “He must’ve been terrible.” No comment on what that means. You can take it as you want.

StyleCaster Daily
Get the latest news and style intel delivered to your inbox.

By providing your information, you agree to our Terms of Use and our Privacy Policy. We use vendors that may also process your information to help provide our services. This site is protected by reCAPTCHA Enterprise and the Google Privacy Policy and Terms of Service apply.

PMC Logo
StyleCaster is a part of Penske Media Corporation. © 2026 SheMedia, LLC. All Rights Reserved.