Kanye West Claims He Hooked Up With Madonna And Ashley Olson

Kanye ‘Ye’ West has continued his slew of surprising statements on X, formerly Twitter. This time, the “Heartless” rapper, who’s been in the headlines over the last several weeks due to his problematic social media posts, claimed he had private affairs with Madonna and Ashley Olsen.

The posts from Kanye West come weeks after the 47-year-old received much backlash for sharing harmful statements about Beyoncé and Jay-Z‘s children online. Following that, the father of four went on another rant and laid into Frank Ocean, who allegedly pressed the rapper for supporting Donald Trump in 2016.

In an X post, West claimed he made out with the “Material Girl” singer during a previous encounter.

“When I made out with Madonna she was bragging about how she f-cked Basquiat and PAC,” wrote the rapper. “I was like d-mn she love to brag just like meee.”

Of course, it’s unclear whether West is being honest; however, according to Complex, Madonna did have relationships with Basquiat and 2Pac in the ’80s and ’90s.

Prior to sharing the alleged information about Madonna, West also claimed he had a previous fling with Ashley Olsen, who rose to fame with her sister in the TV show “Full House.”

“Okay,” he wrote. “I used to f-ck Ashley that’s why the twins got the shot out on [my song] N—as in Paris.” 

For those unfamiliar with the 2011 track, it’s from West’s joint album with Jay-Z, “Watch the Throne.” The track, which peaked at No. 5 on the Billboard Hot 100, features the lyrics, “Prince Williams ain’t do it right, if you ask me / ‘Cause I was him, I would have married Kate and Ashley.”

West’s statement, however, isn’t the first time he’s been linked to the Olsen sisters. Not only was the “Stronger” rapper spotted making out with Mary Kate in 2011, but according to Diplo, the Olsen twins were in the recording studio during the production of “Watch the Throne,” and West referred to them as his “thermometer for what white girls listen to.”

Before his confessions about his alleged encounters with Olsen and Madonna, another post of West going off on Ocean, 37, made its way around online. According to West, Ocean approached him in 2016 and confronted him over his support of then-presidential nominee Donald J. Trump.

However, West, who’s continued to proclaim his support for the 45th and 47th president, took issue with Ocean’s words, especially considering their 10-year age gap.

“Frank Ocean p-ssy -ss come over my house talking about Trump all day and how I shouldn’t support Trump,” he said. “N—a fuck you know about politics and n—a I’m your motherf-cking senior, OG, y’all used to come on tour with me n—a.”

He continued, “None of these n—as as talented [as me]. I’m the greatest motherf-cking artist that ever existed. They can just be slightly better at one thing cause they do that one thing.”

West’s problematic comments about the above celebrities weren’t all the troubled rapper had to say online, though. In early March 2025, West went after his longtime friends and collaborators, Beyoncé and Jay-Z, and shared reckless statements about their youngest children, Rumi and Sir, in a series of posts.

“WAIT HAS ANYONE EVER SEEN JAY Z AND BEYONCES YOUNGER KIDS(?)” he wrote. “THEYRE RETARDED NO LIKE LITERALLY AND THIS IS WHY ARTIFICIAL INSEMNATION IS SUCH A BLESSING HAVING RETARDED CHILDREN IS A CHOICE.”

Later, he shared other concerning posts, claiming Jay-Z, whose real name is Shawn Carter, would try to “k-ll” him for making derogatory statements about his family.