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4 Successful Artists Who Were Just as Clueless as You at Your Age

If you feel like you don’t know what to do with your life, don’t fret. They didn’t either.

Ah, young adulthood. While middle-aged folk thoughtlessly peddle the idea that this is the best time of your life, you’re likely more terrified and disoriented than you’ve ever been. In your late teens or early twenties, it seems like every decision you make—choosing a major, applying to jobs, moving out, finding the right Netflix show—is either the first step down the road to success or the first nail in the coffin of your dreams.

Fun, right?

It doesn’t help that the new generation of young idols (Chance The Rapper, Vince Staples, or Tyler, The Creator, for example) are already cashing checks and collecting fans in numbers beyond your scope, and have been for years. Hell, even 19-year-olds like Lil Yachty and Desiigner are more than a few tax brackets above you.

It’s only natural that your aging ass feels way behind, and that million-dollar bank account you once dreamt of looks further away every year. How are you supposed to compete with GRAMMY-nominated 18-year-olds? You’ll never catch up at this rate. What’s the point in even trying?

The truth is that you’re not as late as you think. Although it’s undeniable that years of hard work and preparation are common and integral to the stories of countless successful artists, sometimes all you need is a potent cocktail of talent and opportunity, a couple stiff shots of risk-taking, and a chaser of determination to get a strong buzz going and change your life, no matter your age.

Look no further than these four late-to-the-game players who made 180-degree career pivots in their mid-twenties and still found stardom.

Lil Dicky

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Career began: age 25

Breakout release: age 25

On “Professional Rapper," the title track of his debut album, Lil Dicky emphatically explains to Snoop Dogg that he gave up the safety and stability of his college-educated life to pursue rap, and his having something to lose, compared to rappers from the streets, demands respect.

He wasn’t kidding.

After graduating summa cum laude (read: top 5% in his class) from the E. Claiborne Robins School of Business at the University of Richmond, Lil Dicky found steady work at Goodby Silverstein & Partners advertising agency as an account manager. After turning his monthly progress report into a rap video, the company moved him over to the creative side of the fence, where he wrote copy for ads like the NBA’s BIG campaign.

With a decent career and a good life ahead of him, LD settled down, started a family, and resigned himself to quiet, upper-middle-class success. Wait, no. That’s not right. What I meant to say was that he quit his job at the age of 25 and spent his bar mitzvah money to make the “Ex-Boyfriend” music video, which garnered a million views within its first 24 hours online. One mixtape, 32 songs and 15 music videos later, his savings ran out, leaving Lil Dicky with one choice: fund his debut album on Kickstarter.

Fast forward a couple years, and Lil Dicky’s life gambles have paid off in the form of an XXL Freshman cover and a Platinum single. That’s a pretty decent turnaround.

Danny Brown

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Career began: age 26

Breakout release: age 30

Any profile on Danny Brown will tell you that the West Side of Detroit native has always wanted to be a rapper:

“[My mom] would just read Dr. Seuss books to me over and over again. So when I first started talking, I talked in rhymes.” - Danny Brown, Complex

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With a house DJ for a father, Danny was exposed to hip-hop at an early age, and given his natural talent, his story could have been that of a child prodigy destined for stardom from the beginning. Unfortunately, when his dad left the family and he became the man of the house, his new responsibility forbade him from spending his time so frivolously. At 18, Danny started dealing drugs to constitute an income. At 19, he caught his first case.

Despite envisioning another life for himself, Danny couldn’t easily escape his new reality, a familiar tale from the hood. When he violated his probation by carrying weed, he skipped his court date and ran “for at least five years.”

Eventually, Danny got caught and subsequently served eight months in prison. After his release in 2007, the then 26-year-old was no longer a young prodigy, but he still had the talent. With a “now or never” attitude, music finally became his priority.

It would take him until 2011 to find his signature sound on XXX, the album that broke 30-year-old Danny Brown onto the scene. As one of only two XXL Freshmen in history to make the cover in their thirties, Danny is the quintessential proof that age is just a number.


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Career began: age 26

Breakout release: age 30

If you aren’t yet familiar with TDE’s newly revealed “John Doe 2,” don’t worry; he’ll be around for some time to come judging by the quality of the music he's already released. Since we just ran an in-depth look at the rise of the Inglewood crooner, I’ll summarize:

  • Sir is his actual given name.
  • His mom was a backup singer for Michael Jackson and Tina Turner, and his uncle was Prince’s bassist.
  • SiR rejected the musical life of his family, moved to Hollywood, and almost found himself on the streets after losing his job to drug abuse.
  • In 2012, at 26 years old, SiR dipped his feet into the music industry, encouraged by the success of his brothers.
  • Now known as TDE’s most recent signee, SiR finally left his full-time job at Guitar Center. A month ago.

SiR may have had the clear advantage of music industry connections, but the transition from Guitar Center to one of the most revered labels in hip-hop doesn’t happen without pure, unadulterated talent. SiR’s trajectory runs parallel to labelmate Isaiah Rashad, who was still working at Hardee’s when his music caught the attention of TDE president Dave Free.

So, the next time you clock in for another grueling shift at minimum wage, just remember: that dead-end job could be the means to an end instead.

Action Bronson

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Career began: age 27

Breakout release: age 27

If you haven’t picked up the hint from his food-centriclyrics or gourmet cooking eating show, Action Bronson has an intimate relationship with the culinary arts, so it should come as no surprise that he used to be a respected New York City chef. Seeing as to how that passion still seeps into his craft, it’s fair to say he might have been satisfied with cooking as a lifelong career, but luckily for Action fans everywhere, he broke his leg in the kitchen:

“The transition of me becoming a rapper from having a day-time job happened literally in the snap of a leg. I was working, I broke my leg. Couldn’t work for months, and I became a full-time rapper. That’s how it went.” - Action Bronson, XXL

Instantly, his rapping hobby became his foremost ambition, and he released his breakout debut album Dr. Lecter in 2011 at the ripe age of 27. Now 33, Bronson’s career is at an all-time high: he’s toured with Kendrick Lamar, J. Cole and Eminem, his F*ck That’s Delicious web-series was adapted for television, and the next installment of his Party Supplies-assisted Blue Chips mixtape series, Blue Chips 7000, is among the most highly-anticipated projects in hip-hop.

To all the misguided adults out there, let the stories of these four impressive artists serve as proof that you don’t have to be a teen Snapchat sensation or a young YouTube phenom to set your career in motion.

In an era where memes reign supreme and internet virality is the most surefire deliverer of overnight fame and fortune, it turns out that the recipe for hip-hop success is still chiefly comprised of talent and desire.


By Kareem, whose debut mixtape is expected sometime before 2027. Follow him on Twitter.



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