Diggy Simmons (Artist Analysis)

Many people know Diggy Simmons as a son of Rev Run and from their family reality show, “Run’s House.” On the show, he was the typical younger brother who was also trying to learn about himself and to be comfortable in his individuality. Ten years after the final season of “Run’s House” Diggy is an actor and rapper in his own right, working on BET and gaining his own record deal with Atlantic Records.

According to many interviews, Diggy says that he’s been rapping since he was five years old. But the first time many of us heard him spit was on his first mixtape, The First Flight, which dropped in December of 2009 as a Datpiff exclusive. Diggy would disappear and work on this mixtape all by himself, without help from his older brother, father or uncle, three people that had already been in music in one vain or another. At this point, people knew Diggy had an interest in fashion because of his blog, but his music interest came as a surprise. He worked with people like Khalil Sharrief, Lil Twist, Karina Pasian and many others. This mixtape was downloaded over 50,000 times.

After the release of his first mixtape, he gained some attention by releasing his freestyle over Nas’s “Made You Look.” This freestyle helped him gain the attention of a number of blogs and influential movers and shakers in the music industry, including Kanye West, Pharrell Williams and Lupe Fiasco. Next, he released his Airborne mixtape on Datpiff, which was downloaded over 100,000 times and has features from Chris Brown, Pharrell, Lupe Fiasco, Raekwon, Jacob Latimore and many others. One of his songs with Bei Maejor, “Great Expectations” was a breakout hit and was used in an AT&T commercial. Around this time, Diggy had begun his clothing line Chivalrous Culture and had begun racking up streams and downloads on both of his mixtapes.

Diggy was signed to Atlantic Records and began making his way into the music industry head first. In 2010, he released his third mixtape, Past Presents Future, hosted by DJ Premiere, where he rapped on a number of old school hip hop beats and did a reprise of his hip hop cypher verse. In 2011 he was placed on the XXL Freshman List and was named on of MTV’s Artists to Watch. A number of singles were released/leaked including “Copy, Paste,” Click Clack Away and Do it Like You. His first album “Unexpected Arrival” was released the day before his birthday in 2012. The album featured Tank, Jadakiss and a number of notable names including Clarence Coffee Jr. who was not featured, but credited with lots of vocals and writing. Other singles included “Two Up,” “88” and “4 Letter Word.” Diggy received kudos for his lyricism and subject matter on songs like “Unforgiveable Blackness” and “Glow in the Dark.” Though the album received positive reviews from critics and fans, the album only sold about 22,000 copies the first week. A couple of weeks after UA was released Diggy J. Cole diss, titled “What You Say to Me” was released. The diss was a response to a few unfavorable lyrics J. Cole spit on “Purple Rain” and “Grew Up Fast.” Diggy was only 17 at the time, so people were not surprised when Cole didn’t respond. The diss track made me laugh when it leaked because its like the textbook example of a kid roasting I really like the “long arms, short sleeves” line. Diggy claimed that he didn’t release the track, but some people assumed that the track leaked as a way to combat the unsatisfying sales of his album. By June of 2013, UA had only sold just under 90,000 copies. Diggy claimed that he wasn’t worried about album sales at all.

Diggy continued to tour and work with acts like Jacob Latimore, the OMG Girlz, Mindless Behavior and many others. He announced his fourth mixtape, Out of this World, which would continue the flying/space theme that his image had consisted of thus far, but the mixtape was never released. Between the release of UA and his second album, Lighten Up, Diggy released a number of singles and worked with Omarion, Ty Dolla $ign, Trevor Jackson, B.o.B and many others. However, none of these singles led to a full release. He also acted in a BET original movie (though some places call it a television show, some places say they’re two different things, I’m honestly not sure) called The Start Up, he was in an episode of a show called The Plug, and had a cameo in the 2012 film Parental Guidance. However, his parts in Parental Guidance were cut out of the final version and The Start Up only aired for a very short time, I actually was unable to find any online versions of it anywhere (aside from short clips that people had filmed off of their televisions).

Though Diggy released a few singles and freestyles throughout the years, his absence was considered a hiatus because fans barely received anything new within about a six year time period.

In 2018, we finally saw Diggy re-emerge fully as both an artist and an actor and he apparently has a crazy work out routine. He began playing Doug on Freeform’s Grown-ish and he released his second album, Lighten Up. This album did not receive the reviews that UA did (check out my review on my website), but it was clear that his artistic vision had changed. First, it looks like he’s an indie artist now, though he has a publishing and distribution deal with Empire. The album is more vulnerable than his first, though it has a couple of tracks that I don’t really like and I don’t think really fit in. Similarly, the visuals for the album are…interesting. Particularly, the visual for “Goin” doesn’t seem to fit in with the others. Not only is there a different tone, but they just seem a little off to me. Diggy was known to dougie quite a bit in the Scream Tour days, but that was pretty much it, so it’s not surprising that he doesn’t dance in the video. But the shots of him in the car and then going back to the dancers in the playground, I just don’t get it, but it looked fun.

Diggy’s been rapping for pretty much a decade at this point and I think we’ve seen lots of growth in terms of his subject matter, though his lyrics have not grown much. Of course, lyrics are not the only reason that people listen to rap music. Some songs are just a vibe, some have a great beat, or hook, or whatever and that’s fine. In fact, his songs “Testimony” and “Anchors” are my favorite from his most recent album, just because of their concepts. But I was hoping for a bit more in terms of lyricism. Overall though, I’m just glad he made an album where he felt like he was honest and vulnerable and that he liked it enough to release it. I became a fan of Diggy in the Airborne days and I still listen to him now, so I know I’m a bit biased, but I’m proud of the work he’s done thus far and I hope that he continues to work and to take hiatuses when he feels they’re necessary. After all, he’s human too.