Drakes Relationship With the Kardashians: Kanye Feuds, Kylie Romance

Drake certainly keeps up with the Kardashians. The rapper’s respective relationships with Kanye West, Kylie Jenner and more members of the Kardashian-Jenner family have made headlines over the years.

Before the Degrassi alum met West, he cited the “Jesus Walks” rapper as “the most influential person” in his music career.

“Before I ever got the chance to meet him, Kanye West shaped a lot of what I do, as far as music goes,” he told MTV News in May 2009. “We always, always, always took the time to listen to Kanye’s music and appreciate it beyond. We searched the samples and we find out where his inspiration came from, because he has one of the best ears in music, period. He knows how to recognize great music that’s not his. He knows how to utilize great sounds and great music. So before I met him, I had the utmost respect for Kanye West. I’d even go as far as to say he’s the most influential person as far as a musician that I’d ever had in my life.”

The two rappers went on to work together on several tracks, before their relationship turned tumultuous.

Drake’s beef with West, who married Kim Kardashian in 2014, didn’t stop him from spending time with other members of the famous family, however.

Years after bonding with Kris Jenner, Us Weekly broke the news that Drake was spending time with her youngest daughter. After the former child actor and Kylie were seen flirting with each other at his 33rd birthday party in October 2019, an insider told Us that the Kylie Cosmetics CEO was seeing Drake.

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“Kylie and Drake’s friendship did take a romantic turn recently,” the insider said in November 2019. “At his Halloween party, they were affectionate and clearly there together. They’ve been seeing each other romantically. He also showed up to Kendall [Jenner]’s birthday.”

Time will tell if Drake’s romance with Kylie lasts — or upsets anyone in the Kardashian-Jenner clan. For now, scroll through for a timeline of the ups and downs with the famous family:

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