Drake’s Ups and Downs with the Kardashians: From Feuding with Kanye West to Dating Kylie Jenner

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Drake’s Ups and Downs with the Kardashians: From Feuding with Kanye West to Dating Kylie Jenner

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.” [jwplayer m98MTrI5-l3ahXupL] 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. “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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Drake’s Ups and Downs with the Kardashians: From Feuding with Kanye West to Dating Kylie Jenner

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.” [jwplayer m98MTrI5-l3ahXupL] 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. “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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August 2013

Drake and Kylie seemingly first crossed paths in August 2013 when he performed at her Alice in Wonderland-themed Sweet 16. He was 27 at the time. 

Credit: Courtesy of Kris Jenner/Instagram

September 2013

Kris showered Drake with love at his album release party for Nothing Was Ever the Same in September 2013. 

“Congratulations Drake!! Celebrating The Album Release... What A Great Night!! NOTHING WAS THE SAME,” the momager wrote at the time via Instagram. “#HoldOnWereGoingHome @champagnepapi.” 

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! at the time. "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?"

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January 2015

After throwing minor jabs at each other through their music and respective interviews, Drake and West released their first joint music venture in years in January 2015 on Big Sean’s song “Blessings.” 

Two months later, West called Drake an “amazing sparring partner” during 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.”

Credit: Courtesy of Kylie Jenner/Instagram

December 2015

Drake made headlines in December 2015 when he attended the annual Kardashian family Christmas party.

“Me, my mom, and a photobomb,” Kylie captioned a photo with Kris and Drake from the bash.

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June 2016

Drake gave Kris a shoutout in his 2015 track, “4PM in Calabasas.” 

“I rode big body, widebody, Calabasas road winder /  Sunshinin', waxed tires,” he raps. “See Kris Jenner, I beep twice and I wave / The rest of you boys I blow Keysh right in your face.” 

Later that summer, West appeared at Drake’s OVO Fest for the third time, confirming they were on good terms. 

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2017-2018

As Drake continued to work with West in 2017 — even teasing the possibility of a joint album — he also collaborated with Kylie’s then-boyfriend, Travis Scott, with whom she shares daughter Stormi. 

Following the release of their song “Portland,” Drake rapped on Scott’s 2018 hit “Sicko Mode.”

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May 2018

Drake’s drama with West was back in the news in May 2018 after the “God’s Plan” rapper’s rival Pusha T slammed Drake in the song “Infrared,” which was produced by the Yeezy designer. After exchanging insults on social media, Pusha T revealed that Drake secretly fathered a child on the song “The Story of Adidon.” 

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September 2018

While West denied that he was the one to tell Pusha T about Drake’s son, he apologized to the Canadian rapper for the situation in a series of tweets in September 2018. 

“I did not have any conversations about your child with Pusha,” he tweeted at the time. “I don’t play with the idea of people’s children after I spoke to Wiz [Khalifa] a few years earlier.”

West, however, changed his tune later that month after reports surfaced that Drake once slept with Kim. The speculation was sparked in-part by Drake referencing “Kiki” in his song “In My Feelings.”

“People making rumors or thinking you f—k my wife and you’re not saying nothing … that don’t sit well with my spirit,” West fired back in an Instagram video at the time. “You know, if I had a girlfriend from Chicago, her name was Renita, and you was married to Rihanna, I wouldn’t make no song called ‘Riri.’ So when you’re like, ‘I don’t know where it came,’ you too smart for that bro.”

Kim, for her part, denied hooking up with Drake.

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October-December 2018

Drake publicly accused West of telling Pusha T about his son on HBO’s The Shop in October 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.” 

Things got even more heated after West accused Drake of calling him to try and threaten him.

“So Drake if anything happens to me or anyone from my family you are the first suspect — so cut the tough talk,”  West tweeted at the time. “You trying to be a bully. I never been bullied in my life and I never will be. That’s why I made it this far in a pink polo.” 

Kim also weighed in, tweeting, “@Drake Never threaten my husband or our family. He paved the way for there to be a Drake.”

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October 2019

West, who shifted the focus of his music to be more religious in 2019, had nicer words for Drake during his October 2019 interview with Apple Music’s Beats 1.

“You cannot be of service to God and be mad at your brother next door. I go to Drake’s house, I walk over there with no security, leave my phone number, here’s my cell,” the “Closed on Sunday” musician said. “I ain’t even thinking, I want all blessings for Drake. I’m an ordained minister, if he want me to like, when he finally get married I’ll show up and be like, ‘We’ve had our ups and downs!’” 

Days later, Us broke the news that Kylie was “never too far away” from Drake at his 33rd birthday party in Los Angeles. 

“Kylie was rapping to songs and dancing with her friends while she was next to Drake, but they weren’t dancing together. They seemed to have a connection though,” one source told Us. 

A second source said that they were “enjoying each other’s company.” 

“They were joking around and Kylie was laughing. She seemed to be really happy and in a great mood,” the second source said. “And [she] and Drake seemed very comfortable with each other. There seemed to be an attraction there.”

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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 were in item at the time. 

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August 2021

Drake seemingly threw shade at West on his track "Betrayal."

“All these fools I’m beefin’ that I barely know / 45, 44 (burned out), let it go / Ye ain’t changin’ s—t for me, it’s set in stone,” the Canada native raps on the song.

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November 2021

The two rappers seemingly buried the hatchet when West shared a photo via Instagram of him posing with Drake and J Prince.

Credit: Chris Pizzello/Invision/AP/Shutterstock; Stephen Lovekin/Shutterstock

October 2022

The College Dropout musician gave Drake a shoutout after noticing that he'd liked one of his Instagram posts. "Everyone knows me and Drake have had a rivalry in the past,” West captioned a screenshot showing the "Best I Ever Had" musician's Instagram handle among the likes on one of his photos. "It really warmed my heart to see Drake like one of my post[s].”

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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 appearance on the "Drink Champs" podcast. "Yeah, that was hard," he said, adding that the Certified Lover Boy musician was the "greatest rapper ever."