Tragic Details Of Tommy Hilfiger's Son, Richard

Richard Hilfiger may have grown up in the lap of luxury, but his life has not been completely gold-plated. Hilfiger is the son of designer Tommy Hilfiger and wife Dee Ocleppo Hilfiger — one of the couple's seven children, two of whom are from Ocleppo Hilfiger's previous relationship. Alongside his one-time reality star sister Ally Hilfiger, Richard is one of the better-known Hilfiger kids thanks to his careers in music and fashion. Even then, he is not especially popular in either field, perhaps because of some of the personal issues that have plagued him through the years or perhaps because people that don't have to do the grind to find notoriety sometimes peter out.

A nepo baby before the term was in the zeitgeist, Hilfiger's upbringing gave him the money and connections to enter into music in his young teens. He started palling around and collaborating with people like Swizz Beatz, Kid Cudi, and — wait for it — Chet Hanks. He soon became known in indie hip-hop circles, developing a career under the name Ricky Hil. Hilfiger was poised for massive success after scoring a big label record deal before hitting legal drinking age, but he has never made it beyond the minor leagues in neither music nor fashion. Instead, the famous heir has mostly made headlines for his two arrests, relationship with Rita Ora, and one unflattering profile published by the Observer in 2011. Keep reading for a detailed look at the tragic details of Tommy Hilfiger's son, Richard.

Richard Hilfiger grew up economically privileged, but privilege in no way guarantees smooth sailing. In fact, having more resources can sometimes create pressure for kids as they are expected to excel when given access to the best in schooling and social activities. For Richard Hilfiger, adolescence was difficult because of struggles with restlessness and a tendency to cause trouble due to boredom. Eventually he, received a diagnosis of attention deficit disorder (ADD), a now-outdated term for attention-deficit hyperactivity disorder (ADHD).

Beginning in 1997, Hilfiger was prescribed Ritalin and Concerta to manage his "acting out." Not long after his ADHD was discovered, Hilfiger received a second diagnosis: bipolar disorder. He has referenced his experience with mental illness in various songs, including "Mental Hell," "Sky's Black," "Torture," "Suicide Watch," and "Psych Ward Blues." Many of these songs also reference drugs, especially the cannabis that Hilfiger grew to rely upon to manage his symptoms.

The rapper first started using marijuana in his mid-teens, eventually replacing the pharmaceuticals he was taking for mood regulation and focus with weed. "I used to pretend I was rolling up a joint with my school note paper and act like I was smoking it," he told High Times. "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."

If you or someone you know needs help with mental health, please contact the Crisis Text Line by texting HOME to 741741, call the National Alliance on Mental Illness helpline at 1-800-950-NAMI (6264), or visit the National Institute of Mental Health website.

Richard Hilfiger began self-medicating with cannabis as a teenager, but he was not using drugs illegally when he was arrested in 2010. At the time the police pulled him over in West Hollywood, Hilfiger was a California resident — and though weed was not yet legal for general use, it was medicinally available. Even though Hilfiger had a medical cannabis card with him when the incident occurred, the amount of marijuana in his trunk and the way that it was packaged in separate baggies was used against him. He was arrested on the spot and booked on one count of possession of marijuana for sale, a felony that carried with it a minimum five-year jail sentence.

The news became public shortly thereafter, with TMZ running an especially splashy headline and a side-by-side of Hilfiger's mugshot and his very famous father's photo. The outlet also reported that Hilfiger posted $20,000 bail the evening after his arrest. He maintained his innocence — "he was just fortunate enough to have three ounces of three types of flower to medicate with," the star told High Times — and managed to avoid jail. He was instead ordered into rehab for two months, followed by a year of probation. "He knew he could have gone to prison and it wasn't an easy time for him or his family," a source told The Mirror years later.

Back when Richard Hilfiger began dating Rita Ora in 2014, the aforementioned story in The Mirror noted his 2010 arrest and labeled him a "bad boy" reformed. An anonymous source also claimed, "He had his issues, but when he went to rehab he decided it was time to turn his life around." However, the tabloid's assessment did not reflect the actual truth of the situation. Hilfiger was sentenced to rehab for his marijuana usage, despite cannabis not generally being considered to have addictive properties. Hilfiger has said that rehab started, rather than halted, his bad habits — exposing him to people who promoted other ways of self-medicating such as pills and alcohol.

"When rehab ended they put me on probation for one year, with a pee-test three times a week," Hilfiger told High Times in 2021. "That's when I began self-medicating with alcohol and pills—when I had never drank alcohol or done drugs before. I'd wake up in the morning and have a beer to calm down, and I wasn't even 21 yet—but, I couldn't use a plant that never hurt anyone. It made no sense at all." Hilfiger began taking Ecstasy to deal with the symptoms that he had previously managed with weed, but quickly transitioned to benzodiazepines and opioids. He dropped everything else when he was allowed to use cannabis again post-probation.

In 2011, the Observer published a big profile on Richard Hilfiger, titled, "Isn't He Rich? Rich Hilfiger's Rap Career Is Poised To Take Off." But what should have been a defining career moment was soured by the nature of the article, which didn't exactly paint Hilfiger as being self-aware. In the article, he went on and on about how he didn't see himself as a typical rich, East Coast prep school kid. "I might have gone to school with that kid. That kid might have played video games in my house. Played out in the woods with me, but I didn't turn into that," he said.

Hilfiger told Styleite that he was "really sad" when he read the Observer's article (via HuffPost), but he had no one to blame but himself. Amongst other things, he was quoted using a gay slur, and said he had reached all of his goals as "the best rapper from Connecticut." While Hilfiger may not appreciate the showy displays of wealth he saw from his childhood peers, his own entitlement shone through when he proudly boasted about being banned from all but one music studio in New York, for acts such as peeing in peoples' drinks and drizzling honey on keyboards. The piece was such a train wreck that Vulture picked up the story and labeled it using the header "nepotism" — more than a decade before "nepo baby" became a term du jour.

Richard Hilfiger may have declared himself the "best rapper that was born in Connecticut ever" back in his infamous 2011 interview with Observer, but alas, we never really saw that come to be. Expectations for Hilfiger were much higher than what he ultimately became, given his mainstream label backing. In 2011, shortly after his drug arrest and shortly before that ill-reputed interview, the rapper signed a deal with Warner Bros. Records. While he had previously been signed to Swizz Beatz's Full Service Records, Warner Bros. was a whole other ballgame. "It's so surreal. I worked so hard for this sh*t," he told XXL Magazine at the time the deal was announced.

Though Hilfiger was reportedly signed mostly because he was friends with The Weeknd, who was just taking off and who wanted to work with him, it was anticipated that Hilfiger would similarly hit it big with the help of Warner Bros., who set him up with a big-name producer and a tour. Needless to say, Hilfiger did not become The Weeknd. 

That is not to say that the rapper does not have a small cult following. But for someone who has been making music since 2007, and has released nearly two dozen albums, Hilfiger lacks the name recognition of many of his peers. He has only 61,000 Instagram followers — less than your average low-level influencer or newbie reality star.

One of Richard Hilfiger's biggest claims to fame is his one-time relationship with singer and "The Masked Singer" panelist Rita Ora. Hilfiger and Ora were first reported as an item in early August 2014, after years of knowing each other. By the time Page Six broke the news, it was believed that they had been dating for a few months already. While an exact date is not known, Ora was in a relationship with Calvin Harris up until they split in June 2014, so she rebounded quickly. (Then again, considering that Harris dumped Ora via X, formerly known as Twitter, she can hardly be blamed for trying to move on as fast as possible.) 

When Ora was still with Hilfiger, the pair weathered paparazzi attention well, even when breakup rumors surfaced in December 2015. Though they did not split then, they lasted only another six months. In July 2015, it was reported that the pair ended their relationship and Page Six had all the tea. "Despite reports that the decision by the pop star, 24, and 25-year-old rapper and designer Hil was 'mutual,' we're told that Ricky 'had been troubled by her flirtatious behavior with other people in the music business and on her show 'The X Factor UK,' the outlet claimed. Hilfiger rather grossly rapped about having sex with someone — presumably Ora — on a track released not long after the split. Ora would go on to date a handful of other fellow public figures before marrying Oscar-winning filmmaker Taika Waititi in 2022.

Richard Hilfiger was incredibly lucky to have avoided jail when he was arrested on drug charges in 2010. Unfortunately, it sure seems like the rapper did not really take this experience as a warning to stay out of trouble. Five years after his first arrest, Hilfiger landed in trouble with the law again in an even more publicized incident that did nothing to squash talk of his entitled nature. Hilfiger got into legal hot water in Florida when he lost his temper while trying to enter LIV nightclub at the Fontainebleau in Miami Beach. The bouncer working the door refused to let Hilfiger's friend inside — he was reportedly told he did not meet the dress code — which set Hilfiger ablaze. He punched the bouncer and was arrested shortly thereafter.

It is unclear what sort of state Hilfiger was in at the time of the incident, but news outlets also reported that fire rescue was called to the scene to "give aid" to the star, who refused their services, per NBC Miami (via Daily Beast). He was later taken to a local jail and booked on a multitude of charges, including battery, disorderly conduct, and possession of less than 20 mg of marijuana. Interestingly, no court appearances or sentencing ever made the news.

If there is one area where Richard Hilfiger was set up to succeed, it was in the fashion business. He is, after all, the son of one of the most famous designers on the planet. Tommy Hilfiger has an estimated net worth of $400 to $450 million but, even more importantly, he has connections galore after more than five decades in the apparel game. What's more, his sister Elizabeth Hilfiger has gone on to find success in the fashion world with her own line, Foo and Foo. Despite the leg up, the younger Hilfiger has not found widespread success with his clothing line — although it has held on for quite a while, to give him credit.

Richard Hilfiger first announced his intent to start a fashion brand in July 2016, with a 500-person party at the Raleigh Miami Beach hotel, which is owned by his father. He and his partner, rapper and visual artist Al-Baseer Holly, did not actually release any products until the following June, when their first line of men's socks and underwear hit Macy's shelves. "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," Richard told WWD at the time.