It features contributions from Live Squad, Apache, Dave Hollister, Deadly Threat, Digital Underground, Ice Cube, Ice-T, Poppi, Treach, and 2Pac's stepbrother Wycked among others.

In early 1992, 2Pac started working on a 2Pacalypse Now follow-up album originally entitled Black Starry Night, which was renamed into Troublesome 21 during the recording process.

Several songs recorded for Troublesome 21, including "Keep Ya Head Up", "I Get Around", "Strictly fo' My Niggas" and "The Streetz R Deathrow" were utilised for the new track listing.

[7] AllMusic's Marisa Brown concluded: "though the production sometimes suffers, especially in the middle of the album, where it's utterly forgettable, the record shows a continually developing MC, with increasingly complex lyrical themes, well on his way to becoming nearly unstoppable".

Eric Berman of The Source wrote: "a combination of '60s black political thought and '90s urban reality, 2Pac is not afraid to speak his mind ... [balancing] the gangsta tendencies of street life with insightful revelations".

[9] Jonathan Gold of Los Angeles Times found the production accomplished and 2Pac's raps "sort of entertaining" but regarded him as "a gifted mimic" with "no discernible style of his own" and "not an especially deep thinker".