Keep Ya Head Up released on October 28, 1993 features R&B singer Dave Hollister and is dedicated to his godson Elijah, Corin Wray (Daughter of Salt) from Salt-N-Pepa and Latasha Harlins. Tupac emphasizes the abuse black women face in the society. The beat is sampled from Zapp's "Be Alright" and the chorus is taken from The Five Stairsteps' "O-o-h Child".

I Get Around was released on June 10, 1993 as the album's second single and features Shakur's mentor Shock G and Money-B of Digital Underground, Shakur's old group. It was produced by Shock G, who produced it under the alias, The D-Flow Production Squad. AllMusic notes that in the song Shakur "brags about his sexual conquests". Chart-wise, it was the album's most successful single reaching number eleven on the Billboard Hot 100 charts.

Holler If Ya Hear Me was released on February 4, 1993 as the album's lead single. The track, which samples "Do It Any Way You Wanna" People's Choice and Public Enemy's "Rebel Without a Pause", is an anthem of resistance. Frustrations with black poverty, police injustice, and Tupac's perceived persecution from political figure Dan Quayle fuel the majority of the track. The song is autobiographical in nature, referring to various traumas experienced by Tupac himself and the editor of Vibe was quoted in TIME magazine as stating that the song struck a chord with a large section of disaffected youth.

Papa'z Song released on January 17, 1994 features Mopreme Shakur under the stage name Wycked in the song, Shakur's older stepbrother and son of Mutulu Shakur. A Vibe Tribe remix of Papa's Song as well as Peep Game ft Deadly Threat and Cradle to the Grave appears on the tracklist. A music video was made around the time for the single release.