This article contains references of mental health and substance abuse.
As the offspring of a world-famous fashion mogul who has a reported $450 million to his name, you might expect Richard, son of Tommy Hilfiger, to have led an entirely charmed life. But as The Notorious B.I.G., Puff Daddy, and Mase famously once argued, “Mo’ Money, Mo’ Problems.”
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Yes, the nepo baby who may or may not be deserving of his fame may not have wanted for anything while growing up in the most exclusive parts of Connecticut, Greewich. But Hilfiger, who since pursuing a career in emo rap has also become known as Ricky Hil, has still faced his fair share of battles, issues, and challenges: some which life has thrown at him and others which have definitely been of his own making. From mental health disorders and marijuana-based arrests to stints in rehab, slating by the press, and shaming from former girlfriends, here’s a look at 11 times the heavily tattooed star’s story became tragic.
Richard was diagnosed with bipolar disorder and ADHD
Richard Hilfiger’s problems began in elementary school when he was diagnosed with several mental health conditions. The youngster had repeatedly found himself in trouble with teachers due to his restless behavior. He subsequently learned that ADHD and bipolar disorder were the root cause.
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Hilfiger, who later addressed his mental health battles on tracks such as “Suicide Watch,” “Sky’s Black,” and the self-explanatory “Mental Hell,” was given Concerta and Ritalin prescriptions to help control his symptoms. However, in an interview with High Times, the rapper revealed that he later substituted these for a different type of self-medication.
“I used to pretend I was rolling up a joint with my school note paper and act like I was smoking it,” Hilfiger said (via The List). “When I was 15, I finally tried it when a friend offered, but I didn’t do enough to get high. I was a good kid. The first time I actually got high my cheeks hurt from smiling, and I thought to myself, I’ll never be bored again.”
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Richard was dismissed as an outcast at school
Proving that not even a multi-millionaire father can buy you friends, Richard Hilfiger often found himself as something of a loner in his school years. But it wasn’t necessarily his troublesome conduct that left him in the cold.
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Indeed, as he explained to Complex in 2010, Hilfiger was made to feel isolated due to his fashion sense and taste in music. “It wasn’t a private school, but it was in Glenville, Connecticut. So it was a lot of like preppy kids.” While the rest of his classmates preferred to sport Abercrombie & Fitch and Gap, the future rapper’s wardrobe was a little more street.
“I was into hip-hop at the time, so I’m wearing Rocawear and Sean John,” Hilfiger explained. “And to them, that’s not cool. ‘That’s the outcast kid. Let’s make fun of him.’ But they were squares to me.” The man of many names also struggled due to his weight. When asked whether he was a “fat kid” back in the day, he replied, “Yeah definitely. I still got a belly.”
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Richard was arrested for marijuana possession
Richard Hilfiger’s troubles with the law began in 2010 when he was arrested in West Hollywood. And anyone who read his interview in marijuana bible, the High Times, won’t be surprised to learn the reason.
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Indeed, the man who started self-medicating in his mid-teens was pulled over in the early hours of the morning on Sunset Boulevard. The Sheriff’s deputies in question discovered a stash of marijuana on Hilfiger’s person, which he allegedly planned to sell. The rapper was subsequently taken to jail, where he spent the rest of the night. He was later given a bail price of $20,000.
Of course, that’s small change for the son of a wealthy fashion magnate, and Hilfiger was soon allowed to go on his way. It was later reported that the Los Angeles County District Attorney decided against any further prosecution as the amount of marijuana in his possession — two ounces — didn’t meet the half-pound requirement to be classed as an intention to sell. If that wasn’t enough of a let-off, the nepo baby’s valid prescription for the drug means he wasn’t even charged with possession.
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Richard spent two months in rehab
Ricky Hilfiger might have escaped jail time for being caught with a reported two ounces of marijuana on Sunset Boulevard. But he did end up having to spend two months in rehab instead. Luckily, the experience initially appeared to change his life trajectory.
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“He was very much was [sic] a bit of a bad boy,” an anonymous insider told Mirror. “He had his issues, but when he went to rehab he decided it was time to turn his life around. He knew he could have gone to prison, and it wasn’t an easy time for him or his family.”
Hilfiger certainly didn’t try to hide the fact that he attended such a facility. That same year, he named one particular mixtape “Ricky Goes to Rehab” and then another “I Just Got Outta Rehab.” And on Lil Peep’s collaboration “Lost in the Mail,” he rapped (via Genius), “I’ve been to hospitals to try to fix my brain (Fix the brain) / I’ve been to rehab to try to stop the chain (Yeah).” Unfortunately, rehab didn’t prove to be a quick-fix solution.
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Richard’s music career was slated by the press
Despite signing to Swizz Beats’ Full Service Records label, working with Kanye West producer Lex Luger, and collaborating with the likes of Lil Peep and The Weeknd, Richard Hilfiger’s hip-hop career never really took off in the way he no doubt hoped. And the press’ dismissive response to his talents probably didn’t help matters, either.
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Indeed, while Hilfiger attempted to present himself as rap’s next great hope, he was often compared not to his musical heroes but to fellow nepo baby Chet Hanks, son of Tom Hanks. The A.V. Club, for example, was particularly scathing, describing his posturing and penchant for ink as “a desperate appropriation of clichéd signifiers in an attempt to distance himself from his cushy reality.”
As you would expect from such an outspoken star, Hilfiger didn’t take all the criticism lying down. “F*** those people, you know?” he exclaimed in an infamous interview with Observer. “F*** y’all, like, suck my d***. Literally. They know who they are.” Of course, this particular chat only ended up giving his haters even more ammunition.
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Richard was left burned by a newspaper profile
It’s fair to say that Richard Hilfiger didn’t do himself any favors when he opened up to Observer in his own distinctive style. In the 2010 piece, the rapper tried to prove his street credentials by, erm, boasting about his trips to Philadelphia with his super-wealthy family’s bodyguard. And that wasn’t the only revelation that caused a stir.
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Hilfiger also admitted that he used to pleasure himself over photos of the model who’d since become his girlfriend, admitted to vandalizing one particular studio by drawing genitalia everywhere, and claimed that he was “the best rapper that was born in Connecticut ever.” He also deservedly received pushback for using a homophobic slur to describe people addicted to cocaine and alcohol.
So, how did Hilfiger react to all the reactions to the profile? Well, surprisingly, considering his usual combative nature, he didn’t go on the attack. Instead, when asked about the furor at a spring fashion showcase for his father’s Tommy Hilfiger label, he simply replied (via HuffPost) that it made him feel “really sad.”
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Richard was publicly shamed by his ex-girlfriend
Richard Hilfiger’s ears were no doubt left burning after one of his ex-girlfriends talked to The Sun in 2014. Following the news that the rapper was in a relationship with one-time “America’s Next Top Model” host Rita Ora, Celia Kay decided to give the “How We Do” singer some advice, and it essentially amounted to staying away.
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”Ricky is an odd character — quite reclusive and loves smoking weed and drinking beer,” Kay began her character assassination (via AZ Central). She then claimed that Hilfiger was also obsessed with sex and had explicitly stated that he wanted a wealthy girlfriend so that he could give up work and spend his days traveling on private planes.
“Ricky is a player and bad news for Rita or any girl,” Kay continued. “If anything, Rita is welcome to him — although I would warn her to be careful. He’s no angel and I think he’s more than capable of breaking her heart.” And it didn’t take long for such predictions to come true.
Richard split with Rita Ora
Given their eventful romantic histories, few expected Richard Hilfiger and the oft-controversial Rita Ora to go the distance. And the wheels showed signs of falling off just six months into their relationship when the latter revealed (via Yahoo! News) on the Billboard Music Awards red carpet, “My heart feels a bit empty right now — but let’s not go there.”
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Inevitably, reports soon surfaced that the couple had split, with Ora’s apparent desire to crack America cited as one of the reasons. But the pair presented a united front for a further six months, with rumors emerging that they’d even moved into the “I Will Never Let You Down” hitmaker’s North London home.
However, in the summer of 2015, Ora and Hilfiger confirmed that they were no longer an item. “It is amicable between the two and they both made the decision to call it a day due to their work schedules,” one insider told the Daily Mail. However, another anonymous source told Page Six that the Brit’s flirtatious behavior had been the true cause.
Richard’s fashion career failed to take off
In 2016, Richard Hilfiger finally followed in his father’s fashion footsteps by launching his own apparel range. And as you’d expect from a man renowned for his self-aggrandizing, he made some pretty lofty claims. “We have the best-looking waistband in menswear, period,” he told WWD about the Tango Hotel brand he co-founded with skateboarder Stevie Williams and visual artist Al-Baseer Holly.
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Of course, this wasn’t Hilfiger’s first rodeo, as the man who cited disgraced hip-hop mogul Puff Daddy as a sartorial inspiration acknowledged, “I’ve had a couple of false starts and have had a couple of brands that I tried to get off the ground, but this is the first time that it’s really starting to happen for me so I’m excited.”
Tango Hotel, whose slogan is “permanent vacation,” was still going more than a decade later. But just like Hilfiger’s rap career, it didn’t exactly set the world on fire. While his father’s eponymous Tommy Hilfiger label has 15 million followers on Instagram, the nepo baby’s pride and joy has just over 30,000.
Richard lost a close friend and collaborator
In November 2017, Lil Peep became yet another artist from the emo-rap scene to die prematurely, in this case, from an accidental fentanyl overdose at the age of just 21. “He could have been his generation’s Kurt Cobain,” claimed Rolling Stone in one of the many tributes that poured in following the tragic news.
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Having collaborated with Lil Peep on several occasions, including “Lost in the Mail,” “SDI22,” and “Dealer Man,” fellow rapper Richard Hilfiger was understandably left reeling by the loss, too. But instead of releasing a statement on social media acknowledging his friend’s passing, he decided to pay his respects in musical form.
In the 2020 track “Dear Peep,” Hilfiger expresses remorse for failing to call the rapper back shortly before his death, retrospectively warns him about the dangers of living such a hard and fast lifestyle and questions what might have been. “You was born for stardom you gon’ blow up / Just try not to take it too far,” he advises (via Genius) before recognizing that nothing he says can ever bring his regular collaborator back.
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Richard is still haunted by darkness and heartbreak
Richard Hilfiger appeared to lay low for a few years before returning in 2021, kickstarting a prolific run of albums and mixtapes that made even seasoned artists look lazy. But as he explained to The Hype Magazine while promoting “SSDD,” he was still consumed by sadness.
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While discussing his lyrical approach, Hilfiger remarked, “It’s not a lot of thought that goes into it; it’s just a flow of subconscious. But I’m inspired by everyday life. I’m inspired by past heartbreak that still hurts me.” The rapper then went on to add that the art of writing songs serves as a form of therapy, and although they’re often steeped in hard-hitting themes, there is some light at the end of the tunnel.
“I want people that relate to it to try and find the message beneath it all,” Hilfiger revealed about what he’d like his audience to take away from his output. “In a lot of the songs, where I have a lot to say, there’s a hidden message in there. Beneath the darkness, there is a positive message to where I’m offering a solution and help to people who are like me.”
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If you or anyone you know needs help with mental health or substance abuse contact the relevant resources below:
