People may be familiar with Diggy Simmons as Reverend Run’s second-oldest son on the show “Run’s House.” But Diggy has been steadily building a name for himself as an MC — and somewhat of a young fashionista — thanks in large part to his blog and his mixtape, First Flight. And anyone who was still unfamiliar with Diggy took notice when he released a video of himself freestyling over Nas’ “Made You Look” throughout the streets of New York.
“It was really something that I picked up and did on my own,” Simmons explained. “I was just writing for a while and doing my thing. It started off, I was just doing joints off my Macbook on GarageBand.”
“I released my first track this summer and got a cool buzz around it. I released some tracks prior to the mixtape, and then that’s when I started pushing the tape and everything. And then once I pushed it out, a lot of people were aware that I was rapping. Now, since the ‘Made You Look’ freestyle and a lot of people knowing that I signed to Atlantic, many people know [about me].”
Diggy said that freestyling over a beat from one of the greatest MCs of all time was intimidating, so he knew he had to do it justice. It took him almost a month of writing to tackle the record, until one day it finally came to him.
“One day I just got in the studio and blasted it, and I just went off on it. I told at least three people before I was going to do it. They were like, ‘Yo, you got to do that beat justice. That’s a Nas beat.’ I thought doing a nice viral video, that would’ve helped it too.”
He hooked up with Phil Da God, a young director from Atlanta whom he met on Twitter. Phil reached out to Diggy’s manager, and when it came time to shoot the video, Phil happened to be in New York.
The video begins with Diggy bopping his head around 42nd Street with cars passing by, and then it transports you to other locations around the city like the Meatpacking District and the Brooklyn Bridge.
So far the video has received nearly 200,000 views and positive reception. Kanye West even posted the video on his blog, saying, “I KNEW THIS KID WAS [GOING] TO BE FRESH. I KNEW IT!” Diggy said he was honored by the compliment from West.
“Man, it feels good. He’s definitely one of the best. He’s like one of the craziest wordsmiths. His verses are amazing and I look up to him in hip-hop, so that co-sign, definitely once they said it in perspective, it was like, ‘Wow.’ “