For a long time, of all the Simmons siblings, Diggy Simmons looked the most likely to strike out on his own and have a successful career. In recent times, however, his star has faded fast.Thanks to their successful father Rev Run, the Simmons kids will never need to be worried about ‘making it.’ But many of them have still tried to do their own thing in show business.
Debut Album
For Diggy, this meant trying to carve out his own career as a rapper. And for a while, things were looking promising. However, after a great start which drew praise from some huge stars, his debut album bombed in 2012. Complex reported that Diggy sold just 20,000 copies in his first week and quickly became disheartened. It would be years before he made a comeback as he went on a soul search to figure out how much he really wanted to be in music.
In 2018, he finally built up the strength to try again, explaining to XXL that he needed that time away to “find what was important” to him creatively. At the time, he stated that he was excited to start competing again with his hip hop contemporaries after rediscovering his purpose. But sadly, there was no Hollywood ending to his return.
The fans he had attracted during his original run had all grown up and were no longer interested in the youthful sound Diggy used in his music. What had at first been a smart approach from Diggy had now backfired on him. Before Diggy got into rapping, his older brother Jojo Simmons had been the first to try and follow in their dad’s footsteps.
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When Diggy’s turn came, he took a different tactic, never pretending to be something he wasn’t and embracing the comfortable life he’d been blessed with. His softer, poppier music was accessible to his fans while they were young. But they moved on while Diggy didn’t.
Copy Cat
It has also been suggested that Diggy failed to carve out a distinct identity as a rapper. His sound has been described as a carbon copy of Drake. By appearing to copy the style of a much bigger star, Diggy ensured that he would not be taken seriously as a fully grown rapper and would always be seen as more of a novelty.
He has not released a new song since 2019, and his show business career appears to have reached its peak already. But it wasn’t always this way for Diggy. For a long time, he looked destined for stardom in music and acting.
According to Paper magazine, he released his first mixtape, The First Flight, when he was just 14 years old. He also managed to go viral by performing a freestyle of Nas’s Made You Look. This managed to receive co-signs from the likes of Kanye West and even Nas himself.
By the age of just 16, Diggy had scored a spot on XXL’s Freshman Class, as reported in Essence magazine. He also appeared on Billboard’s Artists to Watch list. In 2011, he was nominated for BET Hip Hop’s Rookie of the Year Award. The next year, he released his first album, Unexpected Arrival. And his second album, Lighten Up, came out in 2018.
Impressive Start
According to Paper magazine, the young rapper has already managed to rack up collabs with stars like Bruno Mars, Pharrell, and Jeremih. And he was also reported to be the youngest member of All City Chess Club, the rap collective headed up by Lupe Fiasco.
Despite the trajectory of his career, Diggy himself has said that he wasn’t always sure about chasing a career in the entertainment industry. In an interview with Paper, he was asked if he ever considered avoiding show business.
He said that he did when he was “way younger.”
He explained: “I just got this kind of attitude… where I just wanted to be an individual, I didn’t want anybody to attach me to my family.” But then he had a change of heart as a teenager. When talking about his second album, Diggy was asked what his dad thought of it.
Stamp of Approval
And he said that he really loved it and was proud. Diggy also talked about the positive influence his dad has had on him away from music. He said: “We more just talk about how I should approach day to day life, experiences, relationships.”Although Diggy has been able to turn to one of the greats for advice about rap, he has always formed his own opinions on the art form.
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And for him, it’s all about authenticity. He explained in his interview that for him, it was all about being honest and talking about your own experiences. He said that what really mattered was that your work was genuine and true to who you are. But after his attempted return to hip hop fell flat, Diggy seemed to make his mind up that it wasn’t for him anymore. And while it’s sad that he couldn’t achieve his goals, he can always say that he really tried to do his own thing.
