Drug Dealer- 
Back in the 1980s, Jay-Z was a drug runner in Brooklyn and in Southern New Jersey. He and his crew ran into legal troubles in the early 1990s and Jay decided to focus more on a having a music career than selling crack cocaine.
Chicken Spot- 
Back when he was 17 years old, Jay-Z worked at a local chicken spot in Brooklyn called “Crown Fried Chicken”. Jay returned back to the chicken restaurant in 1998 as part of a photo shoot for Blaze magazine.
Hype man- 
Back in the early 90s, while on tour with Big Daddy Kane, Jay-Z often functioned as a hype man and did cameo appearances in between sets. When Kane would head backstage to change outfits, Jay-Z used to freestyle to the crowd along with Postive K.
Rapper- 
It took a while for Jay-Z to officially release his own retail album in 1996, but he were are 23 years later and Jay-Z is still rapping.
Actor- 
Was Jay-Z really an “actor”? Between the short skits between music videos on “Streets Is Watching” and the small role he played in “State Property” we guess the technical answer is yes.
Author- 
Back in the fall of 2010, Jay-Z released his first memoir titled “Decoded”. Jay-Z had started writing an autobiography in 2003, but pulled the plug on the project after learning how many private details of his life would be made public.
Executive Producer- 
HOV has been the executive producer on many projects over the last 20 years, from the 2013 movie “Great Gatsby” to the “Trayvon Martin Story” to Fort Minor’s debut album “The Rising Tied”. He was also classified as “producer” in the 2014 “Annie” film.
Investor- 
Whether its Tidal, J Hotels, Armand De Brignac, JetSmarter or the handful of other companies that Jay-Z has invested major bucks into, Jay-Z puts his money to work in many places outside of the music industry.
Ghostwriter- 
Jay-Z has been credited with writing lots and lots of rap hits. One of his most famous client was Dr. Dre. Jay-Z is credited with the 1999 hit “Still DRE” from the Chronic 2001 album.
President- 
With the splitting of Rocafella Records in 2004, Jay-Z was offered the position of Def Jam President. Jay-Z held that title during his “retirement” and released a host of platinum selling and multi-platinum selling albums.
Picasso Baby 