Struggle and incarceration surrounded Shakur from an early age. His godfather, Elmer "Geronimo" Pratt, a high ranking Black Panther, was convicted of murdering a school teacher during a 1968 robbery, although his sentence was later overturned. His stepfather, Mutulu Shakur, spent four years at large on the FBI's Ten Most Wanted Fugitives list beginning in 1982, when Shakur was a pre-teen. Mutulu was wanted in part for having helped his sister Assata Shakur (also known as Joanne Chesimard), Tupac's godmother, to escape from a penitentiary in New Jersey, where she had been incarcerated for allegedly shooting a state trooper to death in 1973. Mutulu was caught in 1986 and imprisoned for the robbery of a Brinks armored truck in which two police officers and a guard were killed. Tupac had a half-sister, Sekyiwa, two years his junior, and an older stepbrother, Mopreme "Komani" Shakur, who appeared on many of his recordings.
At the age of twelve, Shakur enrolled in Harlem's famous "127th Street Ensemble." His first major role with this acting troupe was as Travis in A Raisin in the Sun. In 1984, his family relocated to Baltimore, Maryland. After completing his second year at Paul Lawrence Dunbar High School he transferred to the Baltimore School for the Arts, where he studied acting, poetry, jazz, and ballet. He performed in Shakespeare plays, and in the role of the Mouse King in The Nutcracker. Shakur, accompanied by one of his friends, Dana "Mouse" Smith, as his beatbox, won most of the many rap competitions that he participated in and was considered to be the best rapper in his school. Although he lacked trendy clothing, he was one of the most popular kids in his school because of his sense of humor, superior rapping skills, and ability to mix in with all crowds. He developed a close friendship with a young Jada Pinkett (later Jada Pinkett Smith) that lasted until Shakur's death. In the documentary Tupac: Resurrection, Shakur says, "Jada is my heart. She will be my friend for my whole life," and Smith calls Shakur "one of my best friends. He was like a brother. It was beyond friendship for us. The type of relationship we had, you only get that once in a lifetime." A poem written by Shakur titled "Jada" appears in his book, The Rose That Grew From Concrete, which also includes a poem dedicated to Smith called "The Tears in Cupid's Eyes".
In June 1988, Shakur and his family moved once again, this time to Marin City, California, where he attended Tamalpais High School. He joined the Ensemble Theater Company (ETC) to pursue his career in entertainment. His mother's crack addiction led him to move into Leila Steinberg's home with his friend Ray Luv at the age of seventeen and he eventually dropped out of high school. Leila Steinberg acted as a literary mentor to Shakur, an avid reader. Steinberg has kept copies of the books that he read, which include J.D. Salinger's Catcher in the Rye, Jamaica Kincaid's At the Bottom of the River, Herman Melville's Moby-Dick, Eileen Southern's Music of Black Americans, and the feminist writings of Alice Walker and Robin Morgan. Most of these books were read before the age of twenty. It has been said that Shakur was, in fact, more well-read and intellectually well-rounded at that age than the average student in the first year class of most Ivy League institutions. In 1989, Leila Steinberg organized a concert with Shakur's group, Strictly Dope. The concert lead to him being signed with Atron Gregory who set him up with Digital Underground. In 1990, he was hired as a back-up dancer and roadie for up-and-coming rap group Digital Underground.