A Timeline of Kim Kardashian and Ray J’s Decades-Long Rocky Relationship

As Kim Kardashian pushes back against Ray J’s racketeering claims while pursuing her law degree, the mess continues to unfold — so we’re unpacking the chaos behind their rocky relationship.

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

Video will return here when scrolled back into view
The Dangers of Trump’s Close Relationship With Tech Billionaires

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

Ray J and Kim Kardashian (Photo by Michael Tran/FilmMagic)

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

Paris Hilton, Ray J, Kim Kardashian and Serena Williams (Photo by Chris Polk/FilmMagic for Bragman Nyman Cafarelli)

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

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.

Straight From The Root

Sign up for our free daily newsletter.

Latest from The Root

‘In Living Color’: Where Are the Cast Members Now?

‘In Living Color’: Where Are the Cast Members Now?

Thirty-six years later, the Wayans family and the most iconic sketch comedy legends are still remains to be culturally relevant to pop culture today. Here is what the stars are doing now …
Exclusive: Dwayne Johnson, More Black Leaders, Celebs Share Life-Changing Lessons

Exclusive: Dwayne Johnson, More Black Leaders, Celebs Share Life-Changing Lessons

The Root Exclusive Series: Black History Month was established 100 years ago, in February 1926. To commemorate this momentous occasion, 100 Black thought leaders and creators share their collective wisdom and insight for the culture in this ongoing series …
Former Michigan Football Coach Sherron Moore Sentenced After Scandal That Rocked the Sport

Former Michigan Football Coach Sherron Moore Sentenced After Scandal That Rocked the Sport

The 40-year-old was sentenced to 18 months’ probation and fined $1,000 on April 14 after being fired for having a relationship with his former staff member …
Black Clergy React to Trump's Photo Portraying Himself as Jesus

Black Clergy React to Trump’s Photo Portraying Himself as Jesus

Following a social media post by the president depicted himself as Jesus, prominent Black faith leaders voice their outrage …
This TikTok Star's Terrifying Health Scare is a Reminder to Take Care of Our Bodies

This TikTok Star’s Terrifying Health Scare is a Reminder to Take Care of Our Bodies

TikTok star PinkyDoll is sharing yet another unfortunate piece of news about her health. But her message is one that younger folks need to hear …
'TODAY Show' Host Sheinelle Jones Cries Tears Of Joy After Surprise Visit From Special Guests

‘TODAY Show’ Host Sheinelle Jones Cries Tears Of Joy After Surprise Visit From Special Guests

Mother’s Day came early for Sheinelle Jones when her book promotion turned into tears of joy …
The Ultimate Guide to Drummer Travis Barker’s Best Hip-Hop Collabs

The Ultimate Guide to Drummer Travis Barker’s Best Hip-Hop Collabs

After the rocker’s surprise performance with Clipse onstage at Coachella, we’re looking at some of his greatest hip-hop collabs of all time! …
Why Phaedra Parks' 'Men Don't Like Smart Women' Myth Is Nonsense

Why Phaedra Parks’ ‘Men Don’t Like Smart Women’ Myth Is Nonsense

The ‘Real Housewives of Atlanta’ alum is mistaking personal frustration for universal truth …
How The Medicaid Cuts in the 'One Big Beautiful Bill' Could Devastate Black Americans

How The Medicaid Cuts in the ‘One Big Beautiful Bill’ Could Devastate Black Americans

As threats to cut $1 trillion in Medicaid mount, Black Americans may lose access to maternal care, health coverage and economic stability …
Beloved 'Family Matters' Star Shocks Fans With Surprise Health Update: ‘Keep Praying For Me’

Beloved ‘Family Matters’ Star Shocks Fans With Surprise Health Update: ‘Keep Praying For Me’

One of the OG’s on the late-90s hit show is giving fans some truly welcomed news when it comes to their personal health! …
Artemis II Astronaut Victor Glover Gets the Welcome Home of a Lifetime in Viral Video

Artemis II Astronaut Victor Glover Gets the Welcome Home of a Lifetime in Viral Video

After coming back from space, Victor Glover received a warm welcome from his neighborhood that will touch your heart …
You Won't Believe What Happened to This MI Inmate After Being Forced to Live With a Leaking Colostomy Bag For Two Years

You Won’t Believe What Happened to This MI Inmate After Being Forced to Live With a Leaking Colostomy Bag For Two Years

A private insurance company denied a Black Michigan inmate’s $919 surgery because it was “too expensive.” Now, they owe him $307,600,000 …
What Issa Rae Says About Hollywood’s Turn Against DEI Will Make You Mad

What Issa Rae Says About Hollywood’s Turn Against DEI Will Make You Mad

Issa Rae is keeping it all the way real when it comes to Hollywood and how their DEI concerns are affecting Black projects nowadays …
Why Justin Bieber's Emotional Coachella Performance Has Fans Celebrating His Career Growth

Why Justin Bieber’s Emotional Coachella Performance Has Fans Celebrating His Career Growth

After taking his fans down memory lane during his Coachella performance, Justin Bieber left viewers across the internet celebrating his music legacy …
The Wild Time Michael Jackson Saved A Crazed Fan's Life In South Korea

The Wild Time Michael Jackson Saved A Crazed Fan’s Life In South Korea

As we get closer to the “Michael” biopic, videos of Michael Jackson concerts are resurfacing online, and folks can’t get enough of one crazy fan in South Korea who climbed up a crane to reach the artist …
Black Elected Official Raises Alarm as Louisiana GOP Moves to Axe His Office

Black Elected Official Raises Alarm as Louisiana GOP Moves to Axe His Office

Louisiana Republicans are on a mission to get rid of an elected office held by an exonerated Black man …
The Bizarre Reason a Black TikTok Psychic is Appealing $10M Judgement in Idaho Murder Case

The Bizarre Reason a Black TikTok Psychic is Appealing $10M Judgement in Idaho Murder Case

Ashley Guillard is officially appealing the $10 million verdict against her after a jury ruled her TikTok claims about the Idaho student murders were defamatory …
Victor Glover, The First Black Man to Travel To The Moon, Has a Family You Will Love

Victor Glover, The First Black Man to Travel To The Moon, Has a Family You Will Love

Black Excellence: Victor Glover’s deep love for his “Cocoa skin” family will make you proud …
Papoose Gives Claressa Shields Engagement Rumors a Reality Check

Papoose Gives Claressa Shields Engagement Rumors a Reality Check

During a VladTV sit-down, rapper Papoose addressed long-standing engagement chatter regarding his relationship with boxer Claressa Shields …
Incarcerated Mothers Are on the Frontlines of the Black Maternal Health Crisis

Incarcerated Mothers Are on the Frontlines of the Black Maternal Health Crisis

This Black Maternal Health Week, we’re looking at the impact of reproductive injustice on incarcerated Black mothers who face increased health risks …