Ray J is one of Hollywood's greatest oddities. He's relevant far beyond just being Brandy's little brother, and he's a more nuanced figure than many people care to admit. For two decades, he's flown under the radar while still being at the crux of some of pop culture's strangest moments. By the millennium, many knew him as Dorian, or D-Money, on Moesha; others followed his singing career with songs like the Lil' Kim-assisted, Neptunes-produced "Wait a Minute." In 2007, a sex tape with ex-girlfriend Kim Kardashian caused him to shed his child star image.
He considered himself a part of Floyd Mayweather's Money Team, and judging by his erratic 2011 rant on The Breakfast Club, he wanted everyone to know. Ray J's presence in the last decade hasn't been any less peculiar. He struck up a friendship with Whitney Houston before her death in 2012, and more recently, Suge Knight signed his life rights, including the story of his label Death Row, over to the singer. But without question, Ray J's most significant cultural contribution is "Gifts," a relic of VH1's best era of reality dating shows—which naturally couldn't exist without the debauchery of For the Love of Ray J coming first.
In 2008 Lil Wayne and Kanye West were running rap, and a "rappa-ternt-sanga" from Tallahassee was crafting R&B for the club instead of the bedroom. T-Pain's "Bartender" and "Buy U a Drank" were already brimming with intoxication by the time Ray J released All I Feel, his third studio album, that year.
While 2005's "I'm 'N Luv (Wit a Stripper)" was a poetic masterpiece, "Gifts" is less concerned with flowery language. "Say shawty got a name / You looking real fly / You looking real cute / In your birthday suit," he sings. Ray J's use of basic pick up lines show even celebrities lose their cool in a strip club. No lyric better illustrates precisely how different life was in 2008 than "I'm pulling on my cellphone / Flip, flip / You know I gotta sneak and take a pic, pic." It was an era when flip phones reigned supreme and recording everything was taboo.
In 2008, the New York City dancers that inspired Lorene Scafaria's Hustlers were coping with the stock market crash, but Ray J's muses don't seem to have a care in the world. "Gifts" might be about choreography that only a seasoned dancer could execute, but it's surprisingly tame—every woman in the video is fully clothed. The clean version even censors the word "drunk." But the version of the video fans really wanted to see, one that could have made it to BET Uncut, happened on his Bachelor-style dating show the following year.
VH1 provided an alternative to the nearly all-white cast on ABC's The Bachelor with Flavor of Love, which turned then 47-year-old Flavor Flav into television's most eligible bachelor with contestants like Hottie and New York becoming household names. FOL wasn't perfect; the show was riddled with outdated tropes about Black women, but even so, it spurred spinoffs like Rock of Love, I Love New York, A Real Chance of Love, and 2009's For the Love of Ray J, in which 14 women had the chance to date the singer.
"Gifts" was already sitting comfortably at No. 7 on the charts, but Ray J's VH1 show cemented its place in history. Every reality show needs a head bitch in charge. Flavor of Love had New York, and Rock of Love had Heather Chadwell. For the Love of Ray J's most competitive contestant made such an impression that the pilot episode, "A Tall Glass of Chardonnay" was a tribute to her. "I think I'm the perfect girl for Ray because I can put my legs behind my head," Chardonnay said matter-of-factly. The 22-year-old, named for the white wine she downed by the glass, proved she wasn't all talk.
When a group of girls was vying for alone time with Ray, Chardonnay didn't beg. Instead, she dropped to the floor in a full split. "You wanna see tricks?" she asked. "I got tricks. "Shawty got gifts. I got everything," she said, searing "Gifts" into your brain. It was influencer marketing before hashtags. As the season progressed, Chardonnay continued to be a personalized ad for the song. Eight episodes later, Chardonnay turned a date night to the strip club into her show. After little coaxing to hit the stage, she complied. "I'll do one trick for him," she said. "One trick for my man." But what viewers at home didn't know was that it wouldn't just be a modest spin around the pole. She approached the pole with confidence, climbing to the top with the core strength of a pro. When it was time to make her way back to Ray J, she didn't slide down like a firefighter usually does. She jumped from the top, landing on the floor in a split. "Damn! Baby got gifts!" Ray J screamed before showering Chardonnay with dollar bills. Can you blame him for being at a loss for words? He already wrote a song about it. It's hard to say whether the synergy of "Gifts" and For the Love of Ray J was intentional, but it certainly was predictive of TikTok's ability to extend the shelf life of popular songs. If anything, Ray J's legacy has taught us that he's always ten steps ahead of the game.
Kristin Corry is a staff writer.