How Drake’s Personal Relationships Inspire His Most Vulnerable and Emotional Hip-Hop Hits

Love him or not, there is no arguing that rapper Drake is one of Hip-Hop's all-time top artists. With over 170 million albums sold, 10 multi-million world tours, collaborations with popular artists such as Chris Brown and Nicki Minaj, and 13 number-one hit songs, the "Hotline Bling" artist shows no signs of slowing down his winning streak. But behind the record-breaking achievements lie many personal truths in some of his most popular songs. For example, "Too Good" and "Fighting Irish Freestyle," although extremely catchy, are songs about ex-girlfriend Serena Williams, former friends and rivals. Let's explore how Drake’s personal relationships have deeply inspired some of his most powerful songs.

Drake’s Song "Too Good" Was About His Romance With Serena Williams

Drake, like most rappers, has been known to surround himself with many famous and beautiful women. He's also dated a fair share of them, too, despite the fact the star has tried to keep his romantic life as private as possible. One of his most talked-about romances was with tennis legend Serena Williams. The pair were first rumored to be dating in early 2011 after Drake sent a rather racy message to Williams on Twitter (X), which was followed by his attending one of her matches soon after. While social media and headlines went wild with speculation, it appears that their relationship fizzled after that. The pair was then rumored to be dating again on and off throughout 2011 and 2015. According to US Weekly, when a reporter asked Williams what her status with Drake was, she merely responded, "We’ve been friends for, like, so many years. Just like family.” After Drake attended several more tournaments, fans seemed to get confirmation that the two were an item after they were captured kissing outside a restaurant by paparazzi. However, Williams continued to deny their courtship, and she shocked the public when she began openly dating her now-husband, billionaire Alexis Ohanian. The pair famously married a year later and welcomed two children in 2017 and 2023. Drake also moved on, welcoming son Adonis with ex-girlfriend Sophie Brussaux in 2017.

Williams and Drake's relationship became the focus of tabloid fodder again when the former danced along to a diss track about Drake, "Not Like Us", by longtime rival Kendrick Lamar, at the 2025 Super Bowl halftime show. At the time of their breakup, it was said that the two didn't part ways amicably but remained friends. However, many headlines painted a different story, with publications such as StyleCaster claiming that Drake's 2022 song "Middle of the Ocean" contained a diss lyric against Williams's husband. Then, in 2024, nearly ten years after their initial breakup, Drake finally confirmed he had dated Williams during a video clip he posted on social media in which he confided to his mother, Sandi Graham, that his 2016 song "Too Good" ft Rihanna was about Williams. “I get heavy on a couple joints, but this is more about me and Serena,” said Drake. “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. 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.”

Drake Dissed Kendrick Lamar and Former Friends in the Song “Fighting Irish Freestyle”

It's no secret that Drake and Kendrick Lamar have been engaged in a personal and artistic feud for some time. While the two have slung jabs at each other throughout their careers for years, the battle intensified when Lamar released his 2024 hit single "Not Like Us." The song accuses Drake of courting underage girls, an allegation which Drake vehemently denies. That is why Drake claims "Not Like Us" is not merely a diss track but contains damning lyrics that have defamed his character and jeopardized his safety. The track propelled the "Passionfruit" singer to sue their joint label, Universal Music Group, for defamation and harassment, alleging that the company had distributed and promoted Kendrick Lamar's track. Although the outcome of the trial has yet to be determined, Drake has already won several small legal victories in the lawsuit, including access to Lamar's salary.

During the height of their feud, Drake had some choice words, not only for Lamar but also for former friends. According to the publication Hot New Hip Hop, Drake's hit song from early 2025, "Fighting Irish Freestyle," is a direct response to those who sided with Lamar over him.

That n**** pulled a rabbit out a hat, I know you love a magician / It's funny to see y'all rejoicing and hugging and kissing.

-"Fighting Irish" - Drake

The song also adds the scathing lyrics.

Nothing Was The Same' with all you b***hes and nothing's forgiven" and " The world fell in love with the gimmicks, even my brothers got tickets, seemed like they loved every minute.

According to Hot New Hip Hop, due to his ongoing feud with UMG, the record label removed the track produced by Conductor Williams from YouTube, citing copywriting issues. Despite the takedown, the song was a hit with fans.