Tupac was sentenced to four and a half years in prison in the sexual assault case. His third solo album, Me Against the World (1995), started out in the number one spot on the album charts. Many critics praised the work, noting that tracks like "Dear Mama" showed a more genuine, softer side to the rapper. The possibility of an early death runs through several songs on the album, hinting that he knew he would die sooner or later.

He then headed back to jail, serving eight months in prison, Shakur returned to music with the album All Eyez on Me (1996). Realizing that if he kept up with his destructive activities, he wouldn't be able to tell the world more stories. He soon calmed down and Started releasing more calm, but still tough songs Like "California Love" featuring by famed rapper-producer Dr. Dre and "How Do You Want It" making a strong showing on the pop charts. It appeared to be a golden time for Shakur.