Sigmund Esco Jackson was born on his mother Katherine's 21st birthday in 1951. Nicknamed Jackie by his grandfather, taken from Jackson Boy, he came from an African-American working-class family. He and his eight brothers and sisters grew up in a 2 bedroom house in Gary, Indiana, an industrial town outside of Chicago. In 1964, Jackie's father, Joseph, formed the Jackson Brothers singing group, which included Jackie and his brothers Tito and Jermaine. The group included younger brothers Marlon and Michael playing assorted percussive instruments. By 1966, Joseph made Michael the lead singer and within two years, they emerged professionally under the name The Jackson Five, which was later altered to a numeral 5 after signing with Motown in 1969.
Prior to the group signing with Motown, Jackson wanted to pursue a career in professional baseball. However, he forsook this career once the group hit the big time.
Jackson performed under a high tenor singing voice. He added brief lead parts in some of the Jackson 5's hit singles, including "I Want You Back" and "ABC". In 1973, Jackson released a solo album that failed to chart. After the Jackson 5 became The Jacksons after leaving Motown for CBS Records in 1976, Jackson's role as a vocalist and songwriter increased. He added a lead vocal alongside brother Michael on their top ten Epic single, "Enjoy Yourself", and also added composition on six of the group's albums with Epic. Jackson's voice changed to a lower tenor vocal style during the Epic years. One of Jackson's most successful compositions was co-writing with Michael, "Can You Feel It", which became an international hit in 1981. Jackson began performing more lead vocals as Michael pursued a successful solo career. On their 1984 album, Victory, Jackson performed lead on the song "Wait", while writing the single, "Torture". Notably before the start of the Victory Tour in 1984, Jackson suffered a leg injury that was officially described as a knee injury incurred during rehearsals. However, a former companion of Jermaine Jackson's, Margaret Maldonado, wrote in her 1995 book, Jackson Family Values, Jackson was injured in an automobile accident, a cause of his then wife Enid Jackson running over Jackson with her car, after catching him with choreographer and then-Laker GirlPaula Abdul. Jackson recovered well enough to perform on the last leg of shows in December 1984 in Los Angeles, where Michael announced he was leaving the group. In early 1985, Marlon Jackson joined Michael in leaving the group as well.
Jackie, Tito and Randy became session musicians, vocalists and producers during this time. In 1987, Jackie, Randy, Tito and Jermaine as The Jacksons recorded and released "Time Out For The Burglar", which was co-written as well as lead by Jackie and Randy. The top 20 Belgian hit was included in the soundtrack to the film, Burglar. In 1988, the remaining Jacksons recorded their final Epic album, 2300 Jackson Street, which included Jackie and Jermaine splitting leads on most of the songs. 2300 Jackson Street failed to chart successfully despite the Randy and Jermaine-led "Nothin' (That Compares 2 U)". Randy did not participate in much of the album's promotion as he was working on his solo project leaving Jackie, Tito and Jermaine to promote the album mostly overseas. Afterwards, the group was dropped from the label and each brother went into solo projects. Jackson signed with Polydor and released his first solo album in 16 years, Be the One, in late 1989. The album was a minor hit charting at #89 on the R&B charts. The first single "Stay" was a Top 40 R&B hit while second single "Cruzin'" was a moderate success. In 2001, after years out of the limelight, Jackie, along with his other brothers, returned to the mainstream during a reunion performance with Michael at his 30th anniversary special at Madison Square Garden.
Currently residing in Las Vegas, Jackson at one time ran two record companies, Jesco Records and Futurist Entertainment. His son, Sigmund, Jr., known by the name of DEALZ, released a mixtape off Jesco in 2007. In 2009, he, Tito, Jermaine and Marlon starred in their brief reality series, The Jacksons: A Family Dynasty. In 2012, the quartet began their first tour since the end of the Victory Tour in 1984. The four brothers continue to tour, currently planning to perform a series of shows at the Las Vegas casino circuit.
Jackson was married twice. He married his first wife, Enid Adren Spann (June 27, 1954 – December 20, 1997), in November 1974. A rocky marriage, they initially separated for several months after they married, but later reconciled. They later divorced in 1987. In 2001, Jackson married a second wife, Victoria Triggs. They've also since divorced. With Enid Spann, Jackson has two children, Sigmund "Siggy", Jr. (b. June 29, 1977) and Brandi (b. February 6, 1982).