Ray J’s Ups and Downs Through the Years

Ray J’s life in the spotlight has been anything but predictable.

Ever since he released his debut album Everything You Want in 1997, the singer has been making headlines for his personal and professional life.

While music was his first avenue into Hollywood, the “Sexy Can I” singer found a whole new level of fame when he entered the world of reality TV with shows like For the Love of Ray J, Brandy and Ray J: A Family Business and Love & Hip Hop.

“When I’m in real life, I’m just hella calm, I’m cool,” Ray J told BuzzFeed in 2014. “It’s all about business. It’s all about being on time. It’s all about being professional. It’s all about doing my job. And then the flip side to that is that I live a turnt-up life and my job requires me to turn all the way up, and so that’s what they’re gonna get, you know what I’m saying?”

Related: Everything Kim Kardashian and Ray J Have Said About Their Sex Tape Drama

He said, she said. Kim Kardashian and Ray J’s past relationship is still making headlines nearly two decades later, thanks to the singer’s former manager. During an appearance on the the “Bootleg Kev” podcast in September 2021, Wack 100 claimed that he was in possession of “part two” of the infamous sex tape that the […]

That life has included many highs and lows that have often been documented for public consumption. Take a look back at Ray J’s bumpy road in the spotlight and what could be next:

The Infamous Sex Tape 

A then-unknown Kim Kardashian began dating Ray J in 2003 after meeting him while working as a closet designer for his famous older sister Brandy. During their 3-year relationship, the couple made a sex tape that was released in 2007, the same year that Kim’s Keeping Up with the Kardashians premiered on E!. The footage would bring a whole new level of fame to both parties. “How different would we all be?” Ray J asked on a June 2024 episode of the “Club Shay Shay” podcast when envisioning a life with no sex tape. “How different would this whole f–king thing be? How different would this industry be? Everything would be different. There might not be any OnlyFans and all the things like that. All the opportunities like that. Probably more people would be going to college.”

Related: Kim Kardashian’s Dating History Through the Years

A star-studded love life. Kim Kardashian‘s personal life has been in the spotlight for decades, no matter who she’s dated or married. Since 2000, Kardashian has been married three times. At only 19, she married producer Damon Thomas, who was 10 years older than her. The marriage lasted three years until she called it quits […]

Ray J’s Music Career 

Although Ray J found success as a musical artist — perhaps not as huge as his sister — it was a career he didn’t always see himself participating in. “I never really wanted to do the music thing in the beginning,” he said on an April 2023 episode of The Blackprint. “At the time, I wasn’t ready. I wanted to hang out with my friends. I just wanted to be a young kid exploring the world. I don’t want to say I was pushed to do the music. But it was in my lap because of how the music industry was at the time and how big my sister was, and still is.”

With help from legends such as Pharrell Williams, Rodney Jerkins and the late LaShawn Daniels, Ray J began making music his way. While he found mainstream success with hits like “Sexy Can I,” “One Wish” and “Wait a Minute,” Ray J made headlines when he released the 2013 song “I Hit It First.” In the opening verse, the artist sings: “I had her head going North and her ass going South, But now baby chose to go West.” While fans immediately speculated the song was about Kardashian, Ray J denied the claims saying the song is about a “concept” and said people were going “way too deep.”

Feuding With the Stars

Whether filming Love & Hip Hop for Vh1 or talking about fellow artists, Ray J is never afraid to get into it with other Hollywood stars. In 2011, news broke that Ray J and Fabolous had gotten into a fistfight in Las Vegas. They have since made peace, but not before both parties claimed they won the fight.

In 2023, Ray J also experienced a war of words with Kodak Black where he offered to end the feud by fighting. “It’s a win-win for everybody,” he said via social media.

Mourning the Death of Whitney Houston 

After Whitney Houston was found dead in her Los Angeles hotel room in February 2012, Ray J spoke out about his on-again, off-again girlfriend. “I’ve tried to process the emptiness that I am experiencing. What my heart feels cannot be expressed in words,” he told Us Weekly the month of her death. “The world lost an icon, but I lost my close friend. Nippy, I miss you so much! You were so happy and full of love. Your smile will live in my heart forever.”

Ray J and Princess Love’s Marriage

In 2016, Ray J and Princess Love appeared stronger than ever when they got married in a lavish ceremony. Although they created a beautiful family with kids Melody, 6, and Epik, 4, the couple struggled to maintain a healthy relationship. Although the pair filed for divorce and briefly reconciled multiple times, their latest split in February 2024 appeared much more final. “Ray J and Princess have had an on and off relationship for a long time. And even though they’ve broken up in the past, this time feels very different,” a source told Us Weekly in April 2024. “They’re both walking away knowing for sure that they truly made an effort at saving their marriage.”

Ray J and Brandy’s Sibling Bond

While growing up in the spotlight, Ray J would often make it clear that he and his sister had an unbreakable bond. But in a June 2024 interview, the “One Wish” artist seemingly confirmed their relationship has become more distant. “Brandy’s goals since the beginning have been totally different from [mine],” he said on the “Club Shay Shay” podcast. “As much as you know that we’re all together, some things I gotta, like, try to like stay over here. Lately even certain events I think they been having … I haven’t got the invite and I’m good with that. But I understand why. It’s just a lot of the s–t I’m doing now is just a little more left field, a little more outrageous, a little louder. A little more dramatic. A tad bit distasteful at times.”

Mental Health Struggles 

In June 2024, Ray J was reportedly involved in a physical altercation with Zeus Network CEO Lemuel Plummer outside of rapper GloRilla’s BET Awards afterparty. The incident appeared to take a toll on the singer, who confessed to fans that he was at a “breakin point.”

“To provide for my family and have generational wealth was always the plan. But money is evil and people are bad and I can’t take it anymore!” he wrote via his Instagram Stories in July 2024. “This s–t that is happening is mind blowing. It’s making me suicidal and uncomfortable with the perception of reality.”

If you or someone you know is struggling or in crisis, help is available. Call or text 988 or chat at 988lifeline.org.