Uncle Louie has produced songs for Prince Markie Dee, Wyclef Jean, Nas, LL Cool J, Rev. Run, DMX, Eric B. of Eric B. & Rakim and Jennifer Lopez. Louis became a studio engineer in 1996 working under Prince Markie Dee. Prince Markie Dee and Eric B., of Eric B. and Rakim were his mentors, guiding him into the world of hip hop music production.
Art
Uncle Louie began working with pop artist Romero Britto in 2011 and continues to be close with the Brazilian-born artist. In 2014 Uncle Louie was honored as the subject of a Romero Britto portrait. Uncle Louie creates pop art-based Challenge Coins and has done so for Michael Strahan and high-profile clients.
Social media
In 2009, Uncle Louie joined Twitter with the eponymous handle; he has over three hundred thousand followers. In 2010, Uncle Louie worked with bloggerJessica Gottlieb on a special project to custom build the perfect mom car]. Uncle Louie is a strong believer that social media is a way to personally promote a client and has discussed the value of using a client's Twitter account to reach fans on their behalf, thereby showing celebrities how they can grow their careers through social media. Uncle Louie has a syndicated column on HuffPost that covers a number of topics from entertainment to travel and the luxury lifestyle.
Television appearances
Louis "Uncle Louie" Gregory has a recurring role on ABC and on Newsmax TV. In 2018, Uncle Louie co-starred on the television ABC show The Goldbergs as "Uncle Louie", the Uncle of "Valley Erica" on the 18th episode during the 5th season. In 2019 Uncle Louie became a recurring role on The Goldbergs, co-starring again, in season 6, episode 15. In July 2019, Louis Gregory began his second and concurrent recurring national television role as a Newsmax TV on-air contributor of .
Entertainment manager
In 2008, Uncle Louie began working in the professional wrestling world with Bill Goldberg. Since then Uncle Louie has represented a multitude of talent in various genres from singers, athletes, and artists. In 2008, Uncle Louie opened Uncle Louie Music Group and Uncle Louie Management, serving as president of both companies. The company also offers promotional and collectible merchandise design and manufacturing under various companies as part of the Uncle Louie conglomerate. Some of Louis' first talent signings were Prince Markie Dee and Kool Rock-ski, of the Fat Boys. Recently, Louis worked with artist Eric B. to reunite him with his old partner Rakim of Eric B. & Rakim to celebrate the 30th anniversary of their album "Paid in Full". He was the President of Legends of Wrestling, Uncle Louie promoted live wrestling events in the United States. In 2017, Uncle Louie client Bill Goldberg appeared on multiple episodes of ABC's The Goldbergs after Uncle Louie worked with the show's writer Adam F. Goldberg.
In 2018 Louis "Uncle Louie" Gregory was inducted into the Sachem Hall of Honor Class. He is one of only 20 inductees. The Hall of Honor recognizes alumni who have achieved extraordinary success in their chosen field.
Civil Service
Louis Gregory began his service at 22 years old. He became a Founding member of America's Largest Federal Agency. He rose through the ranks from trainee to the position of Director. In 2019 he retired from service to pursue his dreams.
Farming
Louis Gregory owns a farm in Florida where he has cows, goats, horses, pigs, chickens, honey bees and fruit orchards. His farm was recently the subject of a TV segment on Florida's WSVN channel 7.
On July 22, 2020, Uncle Louis, along with Adam F. Goldberg, launched challenge coins with the Garbage Pail Kids that sold out in mere minutes. These coins honored famous Garbage Pail kids such as Nasty Nick, Weird Wendy and Wrappin Ruth and were licensed by Topps.