Tito recalled playing around with his father's guitar while he was away working on Gary's steel mills. One night, Joseph discovered Tito had been playing his guitar after a string was broken. Initially upset with his son's playing behind his back, he saw their potential. Around 1964, the Jacksons' aunt Wanda, who was a successful professional musician, encouraged Jackie, Tito, and Jermaine to form a band. The Jackson Brothers originally included hometown friends Muffy Jones and Milford Tonna on guitar and drums respectively. By the end of the following year, the group's younger brothers Marlon and Michael joined the instrumental band playing tambourine and congas respectively.
Showing extraordinary talent at a very young age, young Michael began demonstrating his dance moves and singing ability at the age of five. Michael's moving rendition of "Climb Every Mountain" sang at his kindergarten talent show earned him a place in his brothers' group. Before his eighth birthday, Michael was allowed to perform his song-and-dance routine at a talent contest held at Jackie's Roosevelt High School in Gary, helping his brothers win the competition. It was at that point that Tito's junior high school orchestra teacher Shirley Cartman began mentoring the group. She suggested replacing Jones and Hite with talented musicians Johnny Jackson (no relation) on drums and Ronnie Rancifer on keyboards. Tito moved up to lead guitar while Jermaine played bass guitar after several years as a rhythm guitarist.
Evelyn Lahaie, a local talent agent, suggested to Joe to rename the group the Jackson 5 when they performed in her Tiny Tots Jamboree in Gary. After the contest win, the group began playing professional gigs in Indiana, Chicago and across the U.S. Many of these performances were in a string of black clubs and venues collectively known as the "chitlin' circuit". The group also found themselves performing at strip joints to earn money. Cartman got the Jackson 5 a record deal with Gordon Keith's local Steeltown label, and the group began making their first recordings in October 1967. Their first single, "Big Boy", was released in January 1968 and became a regional hit. This was followed by a second single, "We Don't Have to Be Over 21".
The Jackson 5 had a number of admirers in their early days, including Sam & Dave, who helped the group secure a spot in the famous Amateur Night competition at the Apollo Theater in Harlem. The group won the August 13, 1967, competition during the Amateur Night showdown at the Apollo, impressing Motown Records artist Gladys Knight. Knight recommended the group to Motown chief Berry Gordy, but Gordy, who already had teenager Stevie Wonder on his roster, was hesitant to take on another child act because of the child labor laws and other problems involved. The Jackson 5's sound was influenced by many of the biggest stars of the 1960s, including the self-contained funk bands Sly & the Family Stone and The Isley Brothers, Motown group The Temptations, soul legend Marvin Gaye, rock 'n' roll kid group The Teenagers and soul shouters like Wilson Pickett, Jackie Wilson, Stevie Wonder, Joe Tex and James Brown. At the time of their early success, R&B stars, especially coming from Motown Records, were among the most popular musicians; Motown had launched the careers of dozens of the decade's biggest stars, most notably The Supremes, The Miracles, Stevie Wonder, Marvin Gaye, the Four Tops and the Temptations.
By 1968, the Jackson 5 were a headlining act for the All Star Floor Show at Chicago's The Guys' and Gals' Cocktail Lounge and Restaurant. From July 12–27, 1968, the Jackson 5 opened for Motown act Bobby Taylor & the Vancouvers at Chicago's Regal Theater. Like Gladys Knight before him, Bobby Taylor was also very impressed with the boys, and he decided to make the commitment to bring them to Detroit and Motown. Joseph and The Jackson 5 stayed on the floor of Bobby Taylor's Detroit apartment the night of July 22, while Tayler and Motown executive Suzanne de Passe arranged for the Jackson 5 to audition for the label.
On July 23, the Jackson 5 had their Motown audition, for which they performed James Brown’s then current hit "I Got the Feelin'". Berry Gordy was not in attendance, but the audition was videotaped and sent to him in Los Angeles. Gordy's initial reluctance to sign the group disappeared when he finally saw the boys perform. Gordy decided to sign the Jackson 5 to Motown, and hosted a party at his Detroit mansion on November 25, 1968, to introduce them to the Motown staff and stars. Motown began negotiations to buy out the Jackson 5's Steeltown contract, completing the deal in March 1969. By the summer, Bobby Taylor began producing the group's first recordings at Motown's Hitsville U.S.A. recording studio in Detroit. The early Taylor-produced Jackson 5 records were all covers of both contemporary hits and Motown-standards, including Sly & the Family Stone's "Stand!" and their famous rendition of The Miracles' "Who's Lovin' You", written by Smokey Robinson. Gordy moved the Jackson 5 and Joseph to California, and he and Suzanne de Passe began the process of grooming them as the label's next big act, while the rest of the family remained in Gary. While looking for a house in California, Joseph, Jermaine, Tito, and Jackie lived with Berry Gordy, Marlon and Michael lived with Diana Ross in her California home.
Motown's marketing team prepared press kits and other promotional material to begin The Jackson 5's entrance into the mainstream music industry. Motown publicity significantly altered the group's history, publicizing the ages of most of its band mates as younger than they were — Michael's age changed from eleven to nine to make him appear cuter — and identifying unrelated band musicians Johnny Jackson and Ronnie Rancifer as cousins of the Jacksons. In a major marketing coup, Gordy and Motown decided to attach the group to an established star to increase public curiosity. Thus, it was decided that Motown star Diana Ross would "discover" the group as was explained in all early press kits. According to their official Motown biography, referenced in several early interviews and liner notes, Diana Ross (and, in some versions of the story, Berry Gordy alongside her) was introduced to the Jackson 5 by Gary, Indiana's mayor, Richard G. Hatcher, at a benefit concert that the Jackson 5 were described as having played for the mayor in 1969. Impressed, Ross (and Gordy) had the act signed