The album featured a large selection of guest appearances, including singer Mariah Carey and rappers Snoop Dogg, Big Pun and more.
In an interview with HipHopDX, Krayzie Bone spoke on the creation of the album:
I’d have to say that was the easiest album to make because I had so much material and so much stuff backed up. We was fresh, still not that far from being on the streets. I still had a lot of material that I had that I wanted to get off my chest. It was a breeze. A lot of those tracks, I had the ideas [first] and then I went in and laid them straight out. Some of the stuff was from what we didn’t use from Art Of War. On Art Of War, I would basically start the songs off and everyone else would just come in and do what they do. What dudes didn’t use, I just kept stashed away and when it was time work on my album, I just brought them out.[2]
Krayzie Bone wrote and recorded over 150 songs for the album, of which thirty-eight made the album's final cut as a double album.
The album's second single, titled "Paper" was released in October 1999. The song was produced by Krayzie Bone himself. The song's accompanying music video was later released that year.
Thug Mentality 1999 was met with generally mixed to positive reviews from music critics. Stephen Thomas Erlewine from AllMusic wrote: "Krayzie doesn't hesitate to accentuate the already smooth surfaces of his music. Some of these cuts are positively smoove, which stands in direct contrast to the gangstafied lyrics, but that's always been a part of the Bone trademark". The journalist criticized the excessive length of the album, calling it "ridiculously inflated" and adding that "there are enough songs to make a very good record, possibly one of the best things Krayzie has been involved with".[4]Entertainment Weekly's Matt Diehl called it "the best solo release so far from one of the Ohio speed rappers".[5] Pete T. of RapReviews wrote: "Krayzie displays a wide range of flows and deliveries, often on single tracks." He highlighted fast rapping on the track "Heated Heavy", saying that "Krayzie could give Twista a run for his money any day."[7]Soren Baker, in his review for Los Angeles Times, wrote that "the husky-voiced rapper keeps pushing the music's aural boundaries", commending both the production that features "an eclectic range of instruments" and Krayzie Bone's vocal delivery. He also criticized the album's length.[6] Kris Ex of Rolling Stone described Thug Mentality 1999 as "self-indulgent – but consistently engaging", while also taking issue with some of its lyrical content, such as a "vivid date rape" in the track "Look At You Now", which he named "one of the most disturbing moments ever put to wax".[8]The Source magazine's reviewer believed that with this album Krayzie Bone takes a "gigantic step toward establishing himself as a soloist of the highest caliber", praising his vocal performance, ranging from "hard-core and rapid-fire to the softer, more sing-songy".[9] This was also highlighted by USA Today's Steve Jones, who believed that the artist "shows himself adept at a variety of delivery styles". He described the production of the album as "smooth grooves and pounding rhythms".[10]