Shakur began serving his prison sentence at Clinton Correctional Facility on February 14, 1995. Shortly afterward, he released his multi-platinum album Me Against the World. Shakur became the first artist to have an album at number one on the Billboard 200 while serving a prison sentence. Me Against the World made its debut on the Billboard 200 and stayed at the top of the charts for four weeks. The album sold 240,000 copies in its first week, setting a record for highest first week sales for a solo male rap artist at the time. While serving his sentence, he married his long-time girlfriend, Keisha Morris, on April 4, 1995; the couple divorced in 1996. Shakur stated he married her "for the wrong reasons". While imprisoned, Shakur read many books by Niccolò Machiavelli, Sun Tzu's The Art of War and other works of political philosophy and strategy. He wrote a screenplay titled Live 2 Tell while incarcerated, a story about an adolescent who becomes a drug baron.
The album was very well received, with many calling it the magnum opus of his career. It is considered one of the greatest and most influential hip hop albums of all-time. It is his fourth biggest selling album with 2,439,000 units moved to date. Me Against the World won best rap album at the 1996 Soul Train Music Awards.
"Dear Mama" was released as the album's first single in February 1995, along with the track "Old School" as the B-side. "Dear Mama" would be the album's most successful single, topping the Hot Rap Singles chart, and peaking at the ninth spot on the Billboard Hot 100. The single was certified platinum in July 1995, and later placed at #51 on the year-end charts. The second single, "So Many Tears", was released in June, four months after the first single. The single would reach the number six spot on the Hot Rap Singles chart, and the 44th on the Billboard Hot 100. "Temptations", released in August, was the third and final single from the album. The single would be the least successful of the three released, but still did fairly well on the charts, reaching number 68 on the Billboard Hot 100, 35 on the Hot R&B/Hip-Hop Singles & Tracks, and 13 on the Hot Rap Singles charts. Read more about 2Pac here.