Big Greg debuted in 2010 with his "What's It Gonna Be Like" mixtape while attending college. During college, Greg began to draw comparisons to Drake because he could easily create catchy lyrics in addition to singing on tracks. His first major single, "Like A Stripper", received regional acclaim around the south, which lead to many tours. Greg's first award came in 2015 when he won the Hip Hop Artist of the Year at the Charlotte Music Awards International (CMAI). Later that year, riding off his new single and performance from the CMAI, Big Greg sealed a Hollywood Music in Media (HMMA) nomination, for his new hit single "Like A Stripper". In 2016, Greg's song "Matador" won the Matador Green Energy Drink theme song. The same year, his follow up single "You Can Have It All" won the Hollywood Music in Media Awards (HMMA) for song of the year in Hollywood, California.