Dear Mama

Dear Mama was released on 9 February 1995 as the lead single from Me Against the World. It is dedicated to his mother, Afeni Shakur. In it he describes growing up poor and her addiction to crack cocaine, and argues that his love for her outweighs the bad memories. She had put him out of the house at 17. In 1990 she entered a twelve-step program in Norwalk, Connecticut, and after she finished it they reconciled.

Producer Tony Pizarro recalled that Shakur kept referring to the idea of the song in other tracks. Pizarro said Shakur named Joe Sample's In My Wildest Dreams as a musical inspiration, and that he built the beat on that sample before Shakur recorded the vocals. When it was finished he called Jada Pinkett and told her he had written it about their mothers. In a 1995 Los Angeles Times interview he listed Don McLean's Vincent among the songs that moved him. The video was directed by Lionel C. Martin and featured Afeni Shakur and her sister. Because Shakur was in prison, it used a lookalike and footage from the Brenda's Got a Baby video.

It peaked at number nine on the Hot 100, topped the Hot R&B Singles chart and the Hot Rap Singles chart for five weeks, and was certified platinum on 13 July 1995. Rolling Stone placed it at number 18 on its 2012 list of the 50 Greatest Hip-Hop Songs of All Time. The Library of Congress added it to the National Recording Registry in 2009, calling it a moving and eloquent homage to the rapper's own mother and to all mothers struggling to hold a family together in the face of addiction, poverty and societal indifference. Common called it one of the most heartfelt songs he had heard in hip-hop.