Before he became got into the hip-hop industry, Simmons, his parents and his six siblings were all exposed to the limelight on MTV’s reality show, “Run’s House.” The show, which debuted in 2005, focuses on the lives of the Simmons family in Saddle River, New Jersey, paying particular attention to Diggy’s father, Rev, and his career with Run DMC.
Although at 23, Diggy does not have a reality show of his own, he does share his daily adventures on his Instagram account, posting videos of his early morning workouts and his healthy eating habits. Beyond Instagram, you can also catch Diggy on Freeform’s hit-series “Grown-ish” as Doug.
Simmons first began rapping in the late 2000s, when he began his career in 2009 by dropping his debut mixtape, “The First Flight.” Diggy released the “The First Flight” on his personal blog, where over 100,000 followers downloaded the project. The popularity of his mixtape caught the attention of five different record labels, each of whom offered Diggy a deal. With plenty of opportunity, the rapper ultimately decided to sign with Atlantic Records.
In 2010, a year after signing with Atlantic Records, Simmons uploaded a freestyle remix of “Made You Look,” a popular beat by rap icon Nas. The video received praise from many, including Kanye West, who claimed, “I knew this kid was [going] to be fresh. I knew it!”
Not only was Diggy Simmons the youngest member of Lupe Fiasco’s rap collective, but he also dropped a song titled “Oh Yeah,” which featured Lupe Fiasco as well as Pharrell Williams.
His ability to create music that both young and old listeners could enjoy was evident. Simmons went on to drop his second mixtape, “Airborne,” in 2010, and album’s hit song, “Great Expectations” was featured on a national AT&T television commercial. In December of the same year, he shared his third mixtape, “Past Presents Future,” with rap lovers around the world. His third album consists of samples of songs by artists Nas, Rakim and A Tribe Called Quest.
2011 was a big year for Diggy. At the beginning of the year, the rapper was listed on Billboard’s “Artists to Watch in 2011,” and was selected to be part of XXL’s annual Freshmen list. In the summer, the artist went on his first tour, BET’S 106 & Park: Closer to My Dreams Tour, which starred rapper Tyga, boy-band Mindless Behavior, rapper Lil Twist, Jawan Harris and Trevante.
In the fall of 2011, Simmons went on his second tour, Scream Tour: The Next Generation, with artists Mindless Behavior, Jacob Latimore, New Boyz and OMG Girlz. During the tour, Diggy collaborated with popular artists on featured tracks like “Like ‘Em All” by Jacob Latimore, “Mrs. Right” by Mindless Behavior and “Yeah Right” by Dionne Bromfield.
After two successful tours, Diggy released his first-major label single, “Copy Paste,” which quickly earned the No. 24 spot on Billboard’s Hot R&B/Hip-Hop Songs chart in September. Later, Diggy teamed up with director and producer Phil the God to film and produce a music video for “Copy Paste.” Finally, Diggy was given the amazing opportunity to perform his single during the 2011 BET Awards pre-show.
In the fall of 2011, Simmons gave fans a preview of his newest album, “Unexpected Arrival,” by releasing five of the album’s 12 tracks. The five singles included the previously released “Copy Paste” and “Do It Like You,” which included a music video with Def Jams singer Jeremih.
Before the song’s initial release, music critics shared positive reviews and predictions for the remainder of Diggy’s album; their comments only helped to heighten the artist and his album’s success. After the album’s release in March, 2012, it debuted at No. 13 on the U.S. Billboard 200, and by June, the album sold 89,750 copies in the United States.
Although Simmons dropped a few songs after the success of his album, including “Ain’t Bout To Do” in 2014 and “Fakin” in 2015, Simmons disappeared from the studio scene. The artist admitted that he hadn’t shared a full length project in six years due to his OCD, which affected his mental stability and confidence. In a tweet from August, 2018, Diggy said, “For years, I let my irrationalities and the negative perception of others overcome what I perceived of myself.” Whether you’re a fans of Diggy or not, everyone can relate to these ups and downs of life.
I haven’t released a music project in 6 years. All due to overthinking my ideas, my OCD, being too invested in the unknown and the fear of an uncertain outcome. For years, I let my irrationalities and the negative perception of others overcome what I perceived of myself. Wanting
— Diggy (@diggy_simmons) August 3, 2018
After his emotional revelation on Twitter, Diggy published a new single, “It Is What It Is,” on streaming services like Spotify. The music video, which accumulated over 454,000 views, focuses on light music from a gospel choir and violins, in order to highlight and embrace the meaning of Diggy’s lyrics, instead of overpowering the song with heavy background music and loud percussion.
In November 2018, Diggy made a full comeback to the musical scene when he dropped his latest album, “Lighten Up.” The album features eight tracks, including the well-received song “Anchors.” This month, Diggy released a music video for “Anchors,” which has accrued over 71,000 views. Hopefully what’s next for Diggy Simmons will be possible tour dates alongside future music projects.
When Simmons is not on social media promoting his music, he is working toward living a clean and healthy lifestyle. He strives to incorporate exercise into his everyday routine. The artist admits that working out might just be his favorite activity. This past January, Simmons shared with BET Network his outlook on a healthy lifestyle by saying, “Don’t treat it as a race. Don’t look at the finish line. Don’t look at what other people have.”
For more on the fitness junkie and rap icon, follow Simmons on Instagram at @diggysimmons.