After first performing in school functions and supermarkets, the brothers began participating in local talent shows when Jackson was twelve. By then, his younger brother Michael, then seven, had become the official lead singer of the group. In 1965, they changed their name from the Jackson Brothers to the Jackson Five, and won several talent shows around the Gary area. After winning the Amateur Night competition for The Apollo Theater in August 1967, Joe Jackson began to work part-time at the steel mill to help his sons secure a recording contract. The group signed with Steeltown Records in Gary, Indiana, in November of that year. In January 1968, the Jackson Five’s first single, “Big Boy,” was released on the Steeltown label.

In 1969, the Jackson 5 signed with Motown Records in Detroit, and scored several hit songs, including the number-one singles “I Want You Back,” “ABC,” “The Love You Save,” and “I’ll Be There”, but despite his talent as a guitar player, Motown refused to allow Tito to perform guitar on any of the Jackson 5 recording sessions, instead forcing all their guitar parts to be performed by session musicians. As a direct result, Tito’s guitar work did not make its debut until he and the Jacksons left Motown for CBS Records in 1976. He also began writing songs with his brothers during this time. Throughout his tenure as a Jackson 5 and Jacksons member, Tito can be heard on many album recordings, such as “Zippee Doo Da” and “Man Of War.” Tito, along with Jackie, were the most consistently present members of the Jacksons, with Jermaine, Marlon, Michael, and Randy leaving at different times. After the end of the Victory Tour, Tito performed session work and as a record producer. After releasing 2300 Jackson Street, the Jacksons ceased recording work.

Jackson married Delores “Dee Dee” Martes in June 1972 at the age of 18, and the couple divorced in 1988. In 1994, Martes was found dead floating in a swimming pool. The death was originally ruled accidental; however, a Los Angeles businessman, Donald Bohana, was subsequently charged with murdering her and later found guilty of second-degree murder in 2000. He was sentenced 15 years to life in prison.

Jackson began a solo career in 2003 performing as a blues musician in various clubs with his band, which included producer and guitarist Angelo Earl, and a management team that included Ed Tate. In 2007, in the United Kingdom, Jackson appeared as a judge on the BBC celebrity singing competition Just the Two of Us for series two of the show. He replaced singer Lulu, who was a judge on series one. His co-judges were vocal coach CeCe Sammy, musician Stewart Copeland and radio DJ Trevor Nelson. During the tenure of his brothers’ reality series, The Jacksons: A Family Dynasty (2009), which was produced, released, and transmitted after his brother Michael had died, he served as one of the executive producers alongside his other brothers.

In 2016, Tito Jackson joined his brothers and sisters and scored his first solo hit on the Billboard charts with the single, “Get It Baby,” featuring Big Daddy Kane from his album Tito Time becoming the ninth and final Jackson family sibling to place a solo single on the charts. The album was released in Japan late in 2016, and in the U.S on iTunes in April 2017. Since its launch, three singles have been released to radio in the US. The first single, When the Magic Happens, featuring Jocelyn Brown, was released on April 1, 2017. Jackson launched the album for the UK market in September 2017.