14 Saddest Things About A$AP Rocky's Life

From his two chart-topping albums and multiple Grammy Award nominations to the fact he's the babydaddy of one of the world's most lusted after women, rapper A$AP Rocky may seem to have it all. But as anyone remotely familiar with his autobiographical body of work, or indeed his litany of legal troubles, will already know, the New Yorker hasn't always had it so easy.

Yes, like most hip-hop stars, the A$AP Mob member had faced more hardship by the time he reached his late teens than most of us will have to deal with in a lifetime. Incarceration, bullying, homelessness, the death of a loved one. You name it, the young Rocky went through it.

And although he's now super-rich and super-famous, Rocky has still been put through the emotional wringer on a regular basis. Here's a look at 14 of the saddest things about the hitmaker's past and present.

A$AP Rocky suffered major heartbreak at the age of 13 when his beloved older brother Ricky was fatally shot in the city of Harlem. But as the rapper revealed in a Mercedes-Benz commercial titled "Grow Up: Get a Job," the tragedy inspired the rapper to get his life back on track.

"This beat was always there," says A$AP Rocky. "But one day, man, the beat just stopped." After showing a man acting as the star's late sibling lying on the ground, he continues, "My brother moved on, but the beat came back, pulsing through every vein in my body. My older brother Ricky is responsible for me growing up and having a 'real job.'"

Rocky, whose famous braids are also a tribute to his late sibling, revisited the scene of the crime while taking MTV on a tour of his hometown in 2013. Recalling the moment he learned that Ricky, who had previously mentored him in all things hip-hop, had been gunned down, the hitmaker said, "He was so tough I thought he was gonna make it. I didn't think he was gonna pass." 

A$AP Rocky had to spend many of his teenage years without a father figure after his dad was sent to jail for dealing drugs. Adrian Mayers was given a prison sentence when the rapper was aged just 12. And he didn't get out until his youngest son was on the verge of hip-hop superstardom.

Sadly, Mayers, who hailed from Barbados, passed away shortly after his release from pneumonia. Rocky later paid tribute to the man with a heartfelt post on Instagram captioned, "R.I.P DAD, UNTIL WE MEET AGAIN. SEE MY DADDY IN HEAVEN, HE BE DA REALIST G' TTTL."

Rocky also briefly spoke about his late pop while speaking to "The Rickey Smiley Morning Show" in 2012. And the star claimed (via Rolling Out) that there was much more to Mayers than his criminal reputation: "He was a reasonable guy. He had a lot of sense, and a lot of people lack it these days." The New Yorker also sang his dad's praises in a chat with BBC News a year later: "My dad came into this country from Barbados with nothing and he had 12 children and took care of every one of them. He worked hard every day."

After losing both his father Adrian and elder brother Ricky in quick succession, A$AP Rocky suffered more hardship when alongside his mother Renee and sister Erika, he was forced to take up residency in homeless shelters. In an interview with "Hard Knock TV" in 2012, the rapper revealed how difficult it was to be in middle school and without somewhere to call home.

Rocky said, "I was a little embarrassed as a kid but I rejoiced it and I embraced what that is because it made me who I am today. That was really hard for me back then, being kind of like exposed to that kind of lifestyle is crazy."

Now a multi-millionaire with several homes to call his own, Rocky has been keen to pay things forward. In 2020, he donated no fewer than 120 meals to one of the New York homeless shelters he and his family once sought refuge in. The hitmaker even delivered the food to Upper West Side's Regent Family Residence himself.

Following the death of his brother and incarceration of his father, A$AP Rocky and sister Erika were forced to uproot from Harlem to North Carolina while their mother Renee tried to reconnect with her high school sweetheart. And it's fair to say that the Old North State life wasn't for the rapper.

Reflecting on his brief spell there as a teen with Interview, Rocky revealed that he and his sibling lived with his aunt for a while in an upper middle-class neighborhood. Unfortunately, "The Fresh Prince of Bel-Air"-esque hijinks didn't ensue: "I didn't get along with any of the kids. They used to pick on me and tease me and make fun of me at the bus stop. When I went to school, all my friends were the kids from the poor neighborhoods."

In another chat with Esquire, Rocky revealed that he was also picked on while attending New York's Booker T. Washington High School for the size of his manhood. And how did his tormentors learn about this particular physical attribute? Well, the hitmaker disclosed that at the age of 13 he and several of his classmates participated in a 15-person orgy!

As a kid of the streets, A$AP Rocky got into his fair share of fights while growing up. And one particular scuffle at the age of 15 left him permanently scarred. Of course, the injury to his cheek caused by being hit with a gun is no longer the rapper's only facial blemish.

In 2021, Rocky got everyone's attention by sporting the previously unfashionable headwear item known as the babushka. And this wasn't an entirely stylistic choice, either. The rapper had fallen off his Razor scooter while attempting a pop-up wheelie and, left with a noticeable mark on his face, he decided the best way to cover it up was with a silk headscarf.

Luckily, Rocky now appears to be at ease with his war wounds, as he told Dazed Digital, "They just remind you of where you came from and what you have to show for it. The average person doesn't have one kind of look. There are plus-size models, people who are heavy-set modeling lingerie now. My lady hires them all the time. We all have scars or imperfections. I think sometimes your scars bring you back to reality. Embrace it. Make it work for you."

The apple didn't fall too far from the tree when it came to A$AP Rocky. Just six years after seeing his father Adrian receive a lengthy jail sentence for drug dealing, the hip-hop star also found himself serving time for the same offense.

Luckily, for the future hitmaker, he only had to spend two weeks in the notorious Rikers Island. And he even came out of the experience with a new BFF. Yes, in a coincidental turn of events, Rocky ended up sharing his cell with another aspiring rapper as he explained to Rap Radar. The New Yorker said, "My first night in there, I see the Casanova n**** ... laying on the joint with his Air Max bubble. So I'm like, 'Yo, why'd they let you keep your sneakers, b?' He's like 'Yo it's my third time in here' ... For some reason, the n**** just wanted to be my friend, 'cuz I didn't pose as a threat ... Every time they moved me [to another part of the prison], it was with him, coincidentally."

In another interview with Time Out, Rocky admitted that he wasn't exactly remorseful for the reason he got banged up in the first place: "I didn't feel like I was being bad. I can tell you why: The prohibition era! Liquor was f***ing crack back then. Liquor was weed back then, wasn't it?"

In 2015, A$AP Rock cut short an after-party performance for the Sundance premiere of "Dope," the indie coming-of-age movie in which the rapper plays a Californian drug dealer. Indeed, the star played just two songs before making a quick exit. But the dedication he made during his brief set explained why he couldn't carry on.

Just six days previously, close friend, mentor and A$AP Mob co-founder A$AP Yams, aka Steven Rodriguez, had passed away. And Rocky told Billboard that he was still in mourning when he took to the stage: "That performance — that was just going to stop me from crying. I had to address it, because the whole time I was rapping and I wasn't into it, which is sad, but I just gotta keep it real. I can't front."

Referring to the impending funeral, Rocky added, "It's even harder knowing that I gotta fly out in less than an hour just to go bury him. That's the part that eats at me." But the star, who also had to attend Paris Fashion Week in the wake of Yams' death, insisted that he would get back in his zone soon: "It's all about good people with good energy, and the universe keeps producing them to me. I'll be fine. God is good and I keep all hope and faith."

In 2013, shortly after splitting from fellow rapper Iggy Azalea, A$AP Rocky entered into a relationship with Victoria's Secret model Chanel Iman. Within a year the pair had got engaged. Unfortunately, or fortunately in Rihanna's case, they never actually made it down the aisle.

Yes, in the summer of 2014, Rocky called things off after doing some deep soul-searching, as he explained to MTV News: "Me and Chanel broke up in June and I got really depressed, because I knew that she deserves better than me. And that's the truth. Everybody knows it. I don't wanna be the guy to Lauryn Hill her — if you know what I'm saying. I love her so much that I would rather not be with her, than hurt her."

In a sign of maturity, Rocky also revealed that he and Iman are still good friends before going on to describe her as a "princess" and "one of the most beautiful women" he'd ever laid eyes on. The former lovebirds later proved that they'd split amicably by appearing on the cover of Vogue magazine together.

In 2015, A$AP Rocky once again found himself at the center of legal troubles. But on this occasion, it wasn't related to drug dealing, downtown brawls or any other aspect of the thug life. Instead, the rapper was being taken to court by his ex-manager over apparent unpaid commissions.

Geno Sims, who began working for Rocky in 2011, alleged that his former client had breached his contract to the tune of a whopping $1.7 million. According to The Jasmine Brand, the music mogul, who also helped A$AP Ferg and many other members of A$AP Mob rise to fame, argued that his negotiations for various merchandising, record and PR deals had gone unpaid.

In return, Rocky launched a countersuit claiming that his one-time boss had disclosed personal and financial details to third parties. After four years of back-and-forth drama, Rocky and Sims finally managed to settle their differences outside of court and both suits were dropped.

In 2019, A$AP Rocky spent more than a month in a Swedish jail after being charged with the assault of a man in a Stockholm street altercation alongside three members of his entourage. And according to fellow rapper A$AP Ferg, the New Yorker initially had it tough.

In a since-deleted Instagram post calling for his A$AP Mob bandmate's release, Ferg revealed that Rocky was being kept in solitary confinement and that both phone call and visiting privileges had been revoked. He added, "They are trying to keep him there for two weeks and if convicted he will be looking at six years just for defending himself in a fight. He was no way in [sic] form the aggressor in this ordeal. Pray for justice #freeflacko."

Although Rocky was found guilty in a case which essentially sparked an international diplomatic incident, he was released after being given a fine of approximately $1,300 and suspended jail sentence, per ABC News. In the documentary "Stockholm Syndrome," the hitmaker reveals that his time spent in solitary confinement allowed him to reflect further on the relationship he had with his late father Adrian.

A$AP Rocky proved that there was substance to his style on 2013 debut album "Long. Live. A$AP" with a track which touched upon the pressures of fame, and in particular those stars who have succumbed to them. Referencing both Kurt Cobain and Michael Jackson, the Danger Mouse-produced "Phoenix" also saw the rapper confess that he'd had suicidal thoughts himself.

In an interview with MTV News, Rocky revealed that he simply wanted to be as honest as possible about his state of mind: "Those are natural feelings that we all get sometimes. You hurt so bad and you're going through so much pain to the point where sometimes you don't even wanna live anymore. That's how a lot of people think, whether we'd like to admit it or not and that's all I was showcasing."

Rocky, who was speaking shortly after fellow rappers Freddy E and Capital STEEZ took their own lives, believes that getting the subject out in the open can be cathartic: "I'm not glorifying it at all. I'm just basically telling you that sometimes I have suicidal thoughts. And maybe I should seek help, or maybe it's not that deep."

If you or anyone you know is having suicidal thoughts, please call the National Suicide Prevention Lifeline​ by dialing 988 or by calling 1-800-273-TALK (8255)​.

A$AP Rocky had essentially been hailed as the hip-hop world's second coming with his first two chart-topping albums "Long. Live. ASAP" and "At. Long. Last. ASAP." So no doubt it was something of a culture shock when the Billboard 200 position (No.4) and tepid reviews for his 2018 third studio effort "Testing" came in.

In a chat with GQ, the rapper revealed that the title of his then-forthcoming tour, Injured Generation, was heavily influenced by the response to his previous LP: "Yeah, it was inspired by me feeling emotionally discouraged after I put out my album and I felt like the masses didn't get it at the start."

Rocky admitted that the underwhelming reaction to his work had caused him to question his following: "And I guess initially, I was like, 'Man, did my crowd, did my cult following forget how to mosh? How to slam dance, how to f***ing crowd surf, how to go all out?' I mean obviously I'm the pretty motherf***er but for real, I like to go crazy in a mosh, that's what I came here for! As soon as I got here, I went straight to the mosh pit, I didn't even come in this dressing room."

A$AP Rocky always appears to have been a proud Harlem native. He took MTV on a tour of his hometown, paid it tribute in the promo for "A$AP Forever" and has regularly been pictured with his love Rihanna walking around the place. But during an interview with Red Bull Music Academy, the rapper seemed to have become disillusioned with the state of his former stomping ground.

Rocky initially began singing Harlem's praises, adding, "It's a world within its own. It's like a mentality, a look, a pizzazz, a character. You can only get that if you're born and bred Harlem. Or you at least gotta hang around here long enough something man, grow up with somebody from here. But it's hard to imitate. It's a one of a kind thing."

But the hitmaker then admitted that he no longer feels the same whenever he visits, and one recent trip had been particularly disappointing: "I came up for the 4th of July, wasn't nobody, no firecrackers, none of that s*** man. It's just police on every corner, it's no culture. S*** is sad, man."

Having watched both his brother and mentor lose their lives before the age of 27, it's perhaps little surprise that A$AP Rocky believed that he would become a member of the music world's most macabre club.

Speaking to Forbes in 2016, the rapper explained, "My whole time being 27, everyone was like ... 'you're gonna be part of the 27 club' ... I thought I was gonna die. That's some real conceited s*** to say, but I really thought I was special enough to end." Instead of being relieved when he reached his 28th birthday, though, Rocky admits that he was actually slightly upset that he hadn't been beamed up to heaven.

In an interview with Gentleman's Journal, the then-32-year-old New Yorker also appeared to be disappointed about the fact that his youth was well and truly behind him: "I'm an old man dude. When you're 29 going on 30, you're already 30. And once you're 30..."