"Dear Mama" was released on February 21, 1995 as the first single for the album. The single was the most successful of all the singles released from the album. The song is considered by critics, fans, and purists as one of the greatest hip hop songs of all-time, and one of 2Pac's best songs in particular, being ranked number four on About.com's "Top 100 Rap Songs" list
The song topped the Billboard Hot Rap Singles chart for five weeks, the R&B/Hip-Hop Singles for one week, and peaked at #9 on the Hot 100. It also topped the Hot Dance Music Maxi-Singles sales chart for 4 weeks.
It is considered by many to be 2Pac's most emotional and most respected song, and is praised by many artists, (Eminem mentions it as his favorite Tupac song)[2] even by many artists who are not into the hip hop business. In 1998, the song appeared on 2Pac's Greatest Hits. The official remix is produced by Nitty and features Anthony Hamilton on the 2006 release Pac's Life.
Snoop Dogg said in an interview that this song was a introspective side of 2Pac, which made him different from other rappers, because "he went inside", which other rappers couldn't.
The song appeared on FOX Series New York Undercover.
The "Dear Mama" music video was directed by Calvin Caday while 2Pac was incarcerated; thus, a Tupac look-alike had to be used for certain moments in the video. Afeni Shakur was also featured, shown flipping through pages of a photo album containing pictures of a younger Tupac. The video also shows snippets of articles relating to the Black Panthers, alluding to her past history as a member of this political organization.