A Timeline of Kim Kardashian and Ray J’s Decades-Long Rocky Relationship
– MARCH 22: Ray J and Kim Kardashian attend Charlotte Ronson Fall/Winter 2006 Collection at Library Bar on March 22, 2006. (Photo by Stefanie Keenan/Patrick McMullan via Getty Images)
More than 20 years after a sex tape turned Kim Kardashian and Ray J into major players in pop culture, it looks like the two are sparring again. As Kardashian works toward becoming a lawyer, she’s shutting down Ray’s latest claims that she was involved in racketeering — allegations he escalated by threatening to drop a federal RICO case that he added would be “worse than Diddy,” per TMZ.
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Kardashian clapped back in a defamation lawsuit, where she stated that his “entirely false accusations” would put her “dreams of becoming an attorney in jeopardy.” While the mess continues to unfold, it’s time we unpack all the chaos behind this decades-long rocky relationship, way back to where it all began.
Early 2000s Romance
Kim Kardashian and Ray J met circa 2002, when the reality TV phenom was a personal stylist and organizer for Ray’s older sister, Brandy. The two dated on and off from 2003 to 2006, per US Weekly, and their whirlwind romance would eventually make headlines.
Rising Stars Collide
At the time, Kardashian was building her reputation as a stylist and socialite, while Ray J was carving out his own lane in R&B and reality TV — placing them squarely inside Los Angeles’ rising celebrity landscape.
The Sex Tape Filmed
During their relationship, the two recorded a private sex tape while on vacation in Cabo San Lucas, Mexico in 2003 — a recording that would later become the most infamous chapter in both their lives. The tape, titled “Kim Kardashian: Superstar,” reportedly raked in millions.
Kim K and Ray J’s Sex Tape Leaks
Years after the two parted ways, the pair’s sex tape was allegedly leaked. According to Distractify, the tape was picked up for distribution by Vivid Entertainment in 2007.
Kim Settles Vivid Ent. Lawsuit
In 2007, Kim Kardashian sued Vivid Entertainment over the sex tape but ultimately settled for a reported $5 million — the same year “Keeping Up With the Kardashians” debuted. While the tape was mentioned briefly in Season 1, Kim and Ray stayed silent on the footage.
Ray J Drops Diss Track
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In 2013, Ray J dropped “I Hit It First,” a not-so-subtle reminder of the infamous tape and a jab at Kim’s later romances, and allegedly a dig at Kim and now ex-husband, Ye, per US Weekly.
Heated Interviews and Comments
In the 2020s, Ray J publicly discussed the tape and his role in it, claiming that the release was a partnership involving Kardashian and her mother, Kris, not a leak, per the Daily Wire.
Ray J Says They Were All ‘Partners’
Ray J began spilling the tea in 2022, asserting that the tape “has never been a leak. It’s always been a deal and a partnership between Kris Jenner and Kim and me and we’ve always been partners since the beginning of this thing,” per Daily Wire.
Ray Says He ‘Felt Suicidal’ After Tape
“I felt suicidal because when you know something’s real and it’s true and you’re watching a whole family create an empire from a lie they’ve created, it’s heartbreaking and disrespectful to all the entertainers who have been honest and true to their craft,” Ray stated, per the outlet.
Ray J’s 2026 Racketeering Claims
More than 20 years after the tape, Ray J publicly accused Kim of being involved in racketeering tied to their sex tape — even teasing a federal RICO case “worse than Diddy,” per TMZ.
Kim Claps Back
The reality TV phenom stated that she’s never been charged, indicted, or accused of any crime — RICO violations included — saying, “I have never been contacted by a government authority or agency, or a civil litigant, in connection with any alleged or potential criminal activity,” in her defamation lawsuit against Ray, per the media outlet.
Defamation Lawsuit Filed
According to TMZ, Kim Kardashian and Kris Jenner officially filed a defamation lawsuit against Ray J, claiming he had “absolutely no basis” for his allegations. Kim added, “When [Ray J] made these allegations about me and my mother, he had absolutely no basis to make them.”
Kim Fears Claims Could Jeopardize Her Legal Ambitions
In her defamation lawsuit, Kim stated that his “entirely false accusations” would put her “dreams of becoming an attorney in jeopardy,” citing the importance of “moral character” and the successful completion of background investigations.
“I’m worried that I would need to address these entirely false accusations and that they might be taken seriously,” she added, per the outlet.
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