This text incorporates references of psychological well being and substance abuse.

Because the offspring of a world-famous vogue mogul who has a reported $450 million to his title, you may count on Richard, son of Tommy Hilfiger, to have led a completely charmed life. However as The Infamous B.I.G., Puff Daddy, and Mase famously as soon as argued, “Mo’ Cash, Mo’ Issues.”

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Sure, the nepo child who could or will not be deserving of his fame could not have needed for something whereas rising up in probably the most unique components of Connecticut, Greewich. However Hilfiger, who since pursuing a profession in emo rap has additionally turn out to be referred to as Ricky Hil, has nonetheless confronted his justifiable share of battles, points, and challenges: some which life has thrown at him and others which have positively been of his personal making. From psychological well being problems and marijuana-based arrests to stints in rehab, slating by the press, and shaming from former girlfriends, here is a have a look at 11 occasions the closely tattooed star’s story turned tragic.

Richard Hilfiger’s issues started in elementary faculty when he was identified with a number of psychological well being situations. The teen had repeatedly discovered himself in hassle with lecturers attributable to his stressed conduct. He subsequently realized that ADHD and bipolar dysfunction have been the foundation trigger.

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Hilfiger, who later addressed his psychological well being battles on tracks akin to “Suicide Watch,” “Sky’s Black,” and the self-explanatory “Psychological Hell,” was given Concerta and Ritalin prescriptions to assist management his signs. Nonetheless, in an interview with Excessive Occasions, the rapper revealed that he later substituted these for a unique sort of self-medication.

“I used to faux I used to be rolling up a joint with my faculty word paper and act like I used to be smoking it,” Hilfiger stated (by way of The Listing). “After I was 15, I lastly tried it when a good friend supplied, however I did not do sufficient to get excessive. I used to be an excellent child. The primary time I really acquired excessive my cheeks harm from smiling, and I assumed to myself, I am going to by no means be bored once more.”

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Proving that not even a multi-millionaire father should purchase you buddies, Richard Hilfiger usually discovered himself as one thing of a loner in his faculty years. However it wasn’t essentially his troublesome conduct that left him within the chilly.

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Certainly, as he defined to Advanced in 2010, Hilfiger was made to really feel remoted attributable to his vogue sense and style in music. “It wasn’t a personal faculty, however it was in Glenville, Connecticut. So it was quite a lot of like preppy children.” Whereas the remainder of his classmates most popular to sport Abercrombie & Fitch and Hole, the longer term rapper’s wardrobe was a little bit extra road.

“I used to be into hip-hop on the time, so I am sporting Rocawear and Sean John,” Hilfiger defined. “And to them, that is not cool. ‘That is the outcast child. Let’s make enjoyable of him.’ However they have been squares to me.” The person of many names additionally struggled attributable to his weight. When requested whether or not he was a “fats child” again within the day, he replied, “Yeah positively. I nonetheless acquired a stomach.”

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Richard Hilfiger’s troubles with the legislation started in 2010 when he was arrested in West Hollywood. And anybody who learn his interview in marijuana bible, the Excessive Occasions, will not be shocked to be taught the explanation.

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Certainly, the person who began self-medicating in his mid-teens was pulled over within the early hours of the morning on Sundown Boulevard. The Sheriff’s deputies in query found a stash of marijuana on Hilfiger’s individual, which he allegedly deliberate to promote. The rapper was subsequently taken to jail, the place he spent the remainder of the evening. He was later given a bail worth of $20,000.

In fact, that is small change for the son of a rich vogue magnate, and Hilfiger was quickly allowed to go on his approach. It was later reported that the Los Angeles County District Lawyer determined towards any additional prosecution as the quantity of marijuana in his possession — two ounces — did not meet the half-pound requirement to be classed as an intention to promote. If that wasn’t sufficient of a let-off, the nepo child’s legitimate prescription for the drug means he wasn’t even charged with possession.

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Ricky Hilfiger may need escaped jail time for being caught with a reported two ounces of marijuana on Sundown Boulevard. However he did find yourself having to spend two months in rehab as a substitute. Fortunately, the expertise initially appeared to vary his life trajectory.

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“He was very a lot was [sic] a little bit of a nasty boy,” an nameless insider informed Mirror. “He had his points, however when he went to rehab he determined it was time to show his life round. He knew he might have gone to jail, and it wasn’t a simple time for him or his household.”

Hilfiger actually did not attempt to disguise the truth that he attended such a facility. That very same 12 months, he named one specific mixtape “Ricky Goes to Rehab” after which one other “I Simply Acquired Outta Rehab.” And on Lil Peep’s collaboration “Misplaced within the Mail,” he rapped (by way of Genius), “I have been to hospitals to attempt to repair my mind (Repair the mind) / I have been to rehab to attempt to cease the chain (Yeah).” Sadly, rehab did not show to be a quick-fix answer.

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Regardless of signing to Swizz Beats’ Full Service Data label, working with Kanye West producer Lex Luger, and collaborating with the likes of Lil Peep and The Weeknd, Richard Hilfiger’s hip-hop profession by no means actually took off in the way in which he little question hoped. And the press’ dismissive response to his skills most likely did not assist issues, both.

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Certainly, whereas Hilfiger tried to current himself as rap’s subsequent nice hope, he was usually in contrast to not his musical heroes however to fellow nepo child Chet Hanks, son of Tom Hanks. The A.V. Membership, for instance, was significantly scathing, describing his posturing and penchant for ink as “a determined appropriation of clichéd signifiers in an try and distance himself from his comfortable actuality.”

As you’ll count on from such an outspoken star, Hilfiger did not take all of the criticism mendacity down. “F*** these folks, ?” he exclaimed in an notorious interview with Observer. “F*** y’all, like, suck my d***. Actually. They know who they’re.” In fact, this specific chat solely ended up giving his haters much more ammunition.

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It is honest to say that Richard Hilfiger did not do himself any favors when he opened as much as Observer in his personal distinctive model. Within the 2010 piece, the rapper tried to show his road credentials by, erm, boasting about his journeys to Philadelphia together with his super-wealthy household’s bodyguard. And that wasn’t the one revelation that precipitated a stir.

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Hilfiger additionally admitted that he used to pleasure himself over pictures of the mannequin who’d since turn out to be his girlfriend, admitted to vandalizing one specific studio by drawing genitalia in all places, and claimed that he was “the most effective rapper that was born in Connecticut ever.” He additionally deservedly acquired pushback for utilizing a homophobic slur to explain folks hooked on cocaine and alcohol.

So, how did Hilfiger react to all of the reactions to the profile? Nicely, surprisingly, contemplating his common combative nature, he did not go on the assault. As a substitute, when requested concerning the furor at a spring vogue showcase for his father’s Tommy Hilfiger label, he merely replied (by way of HuffPost) that it made him really feel “actually unhappy.”

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Richard Hilfiger’s ears have been little question left burning after one in every of his ex-girlfriends talked to The Solar in 2014. Following the information that the rapper was in a relationship with one-time “America’s Subsequent High Mannequin” host Rita Ora, Celia Kay determined to provide the “How We Do” singer some recommendation, and it basically amounted to staying away.

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”Ricky is an odd character — fairly reclusive and loves smoking weed and ingesting beer,” Kay started her character assassination (by way of AZ Central). She then claimed that Hilfiger was additionally obsessive about intercourse and had explicitly acknowledged that he needed a rich girlfriend in order that he might surrender work and spend his days touring on non-public planes.

“Ricky is a participant and dangerous information for Rita or any woman,” Kay continued. “If something, Rita is welcome to him — though I might warn her to watch out. He is no angel and I feel he is greater than able to breaking her coronary heart.” And it did not take lengthy for such predictions to come back true. 

Given their eventful romantic histories, few anticipated Richard Hilfiger and the oft-controversial Rita Ora to go the space. And the wheels confirmed indicators of falling off simply six months into their relationship when the latter revealed (by way of Yahoo! Information) on the Billboard Music Awards crimson carpet, “My coronary heart feels a bit empty proper now — however let’s not go there.”

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Inevitably, experiences quickly surfaced that the couple had cut up, with Ora’s obvious need to crack America cited as one of many causes. However the pair introduced a united entrance for an additional six months, with rumors rising that they’d even moved into the “I Will By no means Let You Down” hitmaker’s North London residence.

Nonetheless, in the summertime of 2015, Ora and Hilfiger confirmed that they have been not an merchandise. “It’s amicable between the 2 they usually each made the choice to name it a day attributable to their work schedules,” one insider informed the Day by day Mail. Nonetheless, one other nameless supply informed Web page Six that the Brit’s flirtatious conduct had been the true trigger.

In 2016, Richard Hilfiger lastly adopted in his father’s vogue footsteps by launching his personal attire vary. And as you’d count on from a person famend for his self-aggrandizing, he made some fairly lofty claims. “We’ve got the best-looking waistband in menswear, interval,” he informed WWD concerning the Tango Resort model he co-founded with skateboarder Stevie Williams and visible artist Al-Baseer Holly.

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In fact, this wasn’t Hilfiger’s first rodeo, as the person who cited disgraced hip-hop mogul Puff Daddy as a sartorial inspiration acknowledged, “I’ve had a few false begins and have had a few manufacturers that I attempted to get off the bottom, however that is the primary time that it is actually beginning to occur for me so I am excited.”

Tango Resort, whose slogan is “everlasting trip,” was nonetheless going greater than a decade later. However identical to Hilfiger’s rap profession, it did not precisely set the world on fireplace. Whereas his father’s eponymous Tommy Hilfiger label has 15 million followers on Instagram, the nepo child’s satisfaction and pleasure has simply over 30,000.

In November 2017, Lil Peep turned one more artist from the emo-rap scene to die prematurely, on this case, from an unintended fentanyl overdose on the age of simply 21. “He might have been his era’s Kurt Cobain,” claimed Rolling Stone in one of many many tributes that poured in following the tragic information.

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Having collaborated with Lil Peep on a number of events, together with “Misplaced within the Mail,” “SDI22,” and “Vendor Man,” fellow rapper Richard Hilfiger was understandably left reeling by the loss, too. However as a substitute of releasing a press release on social media acknowledging his good friend’s passing, he determined to pay his respects in musical type.

Within the 2020 monitor “Pricey Peep,” Hilfiger expresses regret for failing to name the rapper again shortly earlier than his demise, retrospectively warns him concerning the risks of residing such a tough and quick way of life and questions what may need been. “You was born for stardom you gon’ blow up / Simply strive to not take it too far,” he advises (by way of Genius) earlier than recognizing that nothing he says can ever carry his common collaborator again.

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Richard Hilfiger appeared to put low for a number of years earlier than returning in 2021, kickstarting a prolific run of albums and mixtapes that made even seasoned artists look lazy. However as he defined to The Hype Journal whereas selling “SSDD,” he was nonetheless consumed by disappointment.

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Whereas discussing his lyrical method, Hilfiger remarked, “It is not quite a lot of thought that goes into it; it is only a stream of unconscious. However I am impressed by on a regular basis life. I am impressed by previous heartbreak that also hurts me.” The rapper then went on so as to add that the artwork of writing songs serves as a type of remedy, and though they’re usually steeped in hard-hitting themes, there may be some gentle on the finish of the tunnel.

“I need folks that relate to it to attempt to discover the message beneath all of it,” Hilfiger revealed about what he’d like his viewers to remove from his output. “In quite a lot of the songs, the place I’ve rather a lot to say, there is a hidden message in there. Beneath the darkness, there’s a constructive message to the place I am providing an answer and assist to people who find themselves like me.”

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When you or anybody wants assist with psychological well being or substance abuse contact the related assets under: