Drake and Kim Kardashian Relationship: Unraveling the Mysteries of Drake’s Complex Bonds With the Kardashian Family
Drake keeps up with the Kardashians without a doubt. Over the years, news has been made about the rapper’s ties with Kanye West, Kylie Jenner, and other members of the Kardashian-Jenner family.
The “Jesus Walks” rapper was described by the Degrassi alum as “the most influential person” in his music career before he met West.
“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 continued collaborating on several songs before things got rocky in their marriage. Yet, Drake’s conflict with West, who wed Kim Kardashian in 2014, did not prevent him from socializing with other well-known family members.
Us Weekly broke the news that Drake spent time with Kris Jenner’s youngest daughter years after the two had become close. An insider told Us that Kylie Cosmetics CEO was dating Drake after the former child actor and Kylie were photographed flirting at his 33rd birthday party in October 2019.
“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.”
Drake’s relationship with Kylie may or may not cause friction within the Kardashian-Jenner family; only time will tell. For now, scroll down to see a history of the famed family’s highs and lows:
August 2013
At Kylie’s Alice in Wonderland-themed Sweet 16 in August 2013, Drake appeared to have met her for the first time. At the time, he was 27.
September 2013
At the Never Was Ever the Same album release party in September 2013, Kris lavished Drake with affection.
“Congratulations Drake!! Celebrating The Album Release… What A Great Night!! NOTHING WAS THE SAME,” the momager wrote at the time via Instagram. “#HoldOnWereGoingHome @champagnepapi.”
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The same month, Drake opened up about his relationship with the family. “I’m just a friend. I really like Kylie Jenner a lot, I really like Kendall Jenner.
Everybody’s really nice. Khloé [Kardashian]’s really nice,” he told E! News. “And obviously, you know, the queen of it all — Kris Jenner — she’s my favorite.
She’s the boss. She’s actually in town tonight, I was trying to get her to come through. She might fall through and play a little FIFA, you know?”
January 2015
After making light-hearted barbs at one another in their songs and individual interviews, Drake and West collaborated for the first time in a long time in January 2015 on Big Sean’s song “Blessings.”
Drake was described as a “great sparring partner” by West two months later in an interview with the French website Clique.
“Someone who’s like, ‘Come on, man, get back up!’ I was sitting there getting fat,” West said in March 2015. “Sitting back, just knocked everybody out. And then [Drake] hits the gym, he’s just running around like, pow, 14 hits … I’m like, ‘Whoa.
Let me go to the studio, then. Let’s see what’s happening. Let me get these lyrics up.’ So, that’s where we at right now, that’s where you getting these records from.”
December 2015
Drake’s attendance at the traditional Kardashian family Christmas party in December 2015 garnered media attention. Kylie posted a picture of herself with Kris and Drake from the party, “Me, my mom, and a photobomb.”
2017-2018
Drake collaborated with Kylie’s then-boyfriend, Travis Scott, with whom she shares daughter Stormi, as well as West and West as he continued working with them in 2017. Drake even hinted that they would release an album together.
Drake rapped on Scott’s 2018 smash “Sicko Mode” after the release of their song “Portland.”
September 2018
While West denied telling Pusha T about Drake’s son, he did express regret to the Canadian rapper in a string of tweets in September 2018.
“I did not have any conversations about your child with Pusha,” he says at the time. “I don’t play with the idea of people’s children after I spoke to Wiz [Khalifa] a few years earlier.”
Later that month, though, after rumors that Drake had once had a se*ual encounter with Kim arose, West changed his mind. Drake’s mention to “Kiki” in the song “In My Feelings” contributed to the rumors.
October-December 2018
“I tell him I’m having trouble with my son’s mother. We had a conversation,” Drake said at the time. “Oh this guy’s trolling me. This was like a manipulative, like, ‘I wanna break you’ thing. … I said, ‘Alright, I’m gonna go back to distancing myself again. I know what this is.’”
Two months later, West reiterated that he didn’t tell Pusha T about his son.
“I told you I ain’t tell Pusha about your son,” he tweeted in December 2018. “It’s all love bro but don’t play with me. You stay too close to be playing all these industry games bro. … I would never intentionally try to hurt you bro I never even heard none of the diss records That ain’t my MO never did a diss record.”
November 2019
An insider told Us that Kylie and Drake’s “friendship” took a “romantic turn” 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’s birthday,” the insider said.
A source close to Drake, however, denied that the twosome was in the item at the time.
October 2022
In a since-deleted Instagram post, West claimed that Drake once hooked up with his former mother-in-law, Kris. “DRAKE A F–K YA BABY MAMA’S MAMA. THAT’S REAL WAR,” he wrote in the caption.
The rapper repeated the allegation later that month during an “Drink Champs” podcast appearance. “Yeah, that was hard,” he said, adding that the Certified Lover Boy musician was the “greatest rapper ever.”
April 2023
Drake’s new song, “Search & Rescue,” features a sample of Kim talking about her divorce from West. The audio clip was taken from the Keeping Up With the Kardashians series finale of 2021, where the co-founder of Skims talked about her breakup with her mother. The reality star is heard stating in the song, “I didn’t come this far only to get this far and not be happy. Think about that.
After fans accused the rapper of trolling West with the song, his dad, Dennis Graham, said that wasn’t the case. “Drake is not trolling anyone,” Graham wrote via Instagram, commenting in response to a TMZ story about the sample. “It’s just a song. Why try and create a Kanye and Drake beef again?”
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