A savvy rapper with crossover appeal, Nelly seemed like a novelty when he debuted with the Top Ten pop hit "Country Grammar (Hot...)" in 2000, but he quickly proved to be a legitimate hitmaker with "Hot in Herre," "Dilemma," and "Shake Ya Tailfeather" -- and those three only account for a fraction of his Hot 100-topping and Grammy-winning hits. These feats built the foundation of a career that boasts six consecutive Top Ten albums, from the diamond Country Grammar (2000) to the platinum 5.0 (2010) and "The Fix" (2015), leading to warmly received collaborations in the 2020s.

His debut album, Country Grammar (2000), featured contributions from the St. Lunatics as well as the Teamsters, Lil Wayne, and Cedric the Entertainer, and thanks to the widespread popularity of lead single "Country Grammar (Hot...)," the album debuted at number three on the Billboard 200 album chart, climbing to the top spot soon afterward. In addition to the Top Ten title track, Country Grammar spawned the hit singles "E.I.," "Ride wit Me," and "Batter Up." In the wake of Nelly's remarkable breakthrough success, he recorded a group album with the St. Lunatics, Free City (2001). Released by Universal, the album also charted in the Top Ten and spawned a moderate hit, "Midwest Swing," which cracked the Billboard Hot 100.

The following summer Nelly returned with his second album, Nellyville (2002), and lived up to his self-proclaimed billing as "#1" (i.e., the title of his 2001 hit from the Training Day soundtrack): Nellyville topped the Billboard album chart, while the Neptunes-produced lead single, "Hot in Herre," remained atop the singles chart. In all, Nelly impressively held the number one spot on ten different Billboard charts the week of Nellyville's release, and he remained a chart presence as he released a string of follow-up singles: "Dilemma" (a chart-topper featuring Kelly Rowland), "Air Force Ones" (a Top Three hit), "Work It" (featuring Justin Timberlake), and "Pimp Juice." "Hot in Herre" and "Dilemma" each won Grammy awards -- the former for Best Male Rap Solo Performance, and the latter for Best Rap/Sung Collaboration.

Even after Nellyville ran its course commercially, Nelly's hit streak continued unabated, with "Iz U" (from his stopgap remix album Derrty Versions [2003]) and another Grammy winner, "Shake Ya Tailfeather" (from the Bad Boys II [2003] soundtrack), keeping him in the spotlight while he readied his separately released double-disc Sweatsuit (2004) project (following the lead of OutKast and R. Kelly, who had both recently released very successful two-disc sets). Sweat and Suit were led by a pair of red-hot singles -- "Flap Your Wings" (a club jam) and "My Place" (a slow jam) -- and debuted at the top two spots on the Billboard 200 album chart. Follow-up singles included "Tilt Ya Head Back" (featuring Christina Aguilera), "Over and Over" (Tim McGraw), "Na-Na-Na-Na" (Jazze Pha), and "N Dey Say." Sweat and Suit were later bundled as Sweatsuit (2005), along with the new song "Grillz," itself a number one hit.

The time between the release of Sweat and Suit and that of Brass Knuckles (2008) was the longest Nelly went between albums to date, though he did collaborate frequently (with Ashanti, R. Kelly, and T.I., to name a few) during the intervening period and built his acting résumé. The star-studded 5.0 (2010) featured the singles "Just a Dream" (produced by Jim Jonsin) and "Move That Body" (produced by Dr. Luke and Max Martin, featuring Akon and T-Pain). M.O. (2013), issued three years later, featured numerous tracks with Pharrell, plus Nicki Minaj and NellyFurtado as guest stars. Nellyville, a BET reality series, started airing in November 2014. "The Fix," featuring Jeremih, arrived the following year and was his 27th single to appear on the Hot 100. After a 2018 track with Jaquees, "Freaky with You," Nelly retreated a bit but returned in 2020 with a slew of collaborations with such country artists as Jimmie Allen, Florida Georgia Line, and Kane Brown. This was the prelude to Heartland, a 2021 album that blended country-pop and rap. Along with the 2022 compilation album Still Hot in Herre, Nelly teamed up with country singer Chris Lane for the single "Birthday Girl.