Nelly first came to mainstream audiences with the song, "Country Grammar" (2000) and released Free City with the St. Lunatics in 2001. Country Grammar established him as one of the most successful rappers of the early 2000s with the help of an image one part handsome boy-next-door and one part tough gangster.
From the beginning of his hip hop career, the lyrics of "Country Grammar" explored this dichotomy, posing the question: "Who says pretty boys can't be wild niggaz?" and containing references to gun violence and drug use while also sending shout outs to billionaires Bill Gates and Donald Trump, as well as fictional serial killer Hannibal Lecter.
The album Country Grammar, debuted at number one on the Billboard Top 40. Nelly and Country Grammar were nominated for two 2001 Grammy Awards--Best Rap Album and Best Rap Solo Performance. On July 18, 2001, it was certified 7x platinum.
"Ride wit Me", from the Country Grammar album, was nominated for three 2001 MTV Video Music Awards--Best Male Video, Best Rap Video, and Viewer's Choice; the album won the Best Rap Video award. Nelly was also named "Best New Artist" at the first Annual B.E.T. Awards in 2001.
Other recognitions in 2001 include winning the Favorite New Male Artist award at the 2001 Blockbuster Entertainment Awards and being named one of People's "Breakthrough Stars of 2001".