Born in 1960s Chicago, Dillard’s father abandoned the family, leaving Dillard’s soft-spoken but determined mother Dorothy to chart the path for Dillard and his three siblings. She raised them in Chicago's Mason Court Projects on the east side while also teaching them to look beyond the pain and poverty that encircled them. At one point, all four kids shared a single bedroom in their small apartment, but Mrs. Dillard, who worked as a housing placement specialist, saw it as a temporary circumstance. Dillard says that sharing the same room forced his two sisters and brother to learn to share and become respectful of each other's space. Furthermore, although, they were living in a poor neighborhood, Dillard says what clothes they had were always clean. "My mother saw to it that we always had holiday clothes, she also took us on vacations. She did it all by herself and she made us learn to love each other better." By the time Dillard was in the seventh grade, his mother had moved the family to their own house on the middle-class west side of Chicago Heights.
Although, Dillard began to gain local notice for his musical skills in high school, he had been performing all his life. Since the age of three, Dillard watched church choirs. His Grandma used to stand Little Ricky on top of his baby potty and he would direct and sing. At five years old, he began directing the junior choir at St. Bethel Baptist Church. In 1981 he formed the first gospel choir at Bloom High School. "There were so many church kids there and they liked to sing," he says. "So, I started a group called Ricky Dillard and Company and we sang at school. One of my teachers, Don Bondurant, said, `you should start a gospel choir' and I did." In spite of his love for performing, Dillard thought his future lay in radio announcing. He attended Columbia College for a couple of years, but dropped it because "The curriculum bored me and I was really tired of school anyway." He took a job as a front desk clerk at a Holiday Inn and later worked as a file clerk while performing in a professional back-up group called Love, Salvation & Devotion (LSD) on the weekends.
In 1984, Dillard joined the late Milton Brunson's Thompson Community Singers. At the same time, he started hanging out with renowned club DJ Frankie Knuckles and began recording dance and hip-hop records. Aside from a half dozen-guest appearances on various dance tracks, Dillard recorded his own album "Let The Music Use You" which was released in Europe and was imported into the United States. In spite of his growing success in the club market, Dillard says, "My heart was in the gospel. I always wanted to do gospel. The other stuff was just an opportunity to record. I wanted to bring a more contemporary style into gospel for choirs." It's those contemporary innovations in gospel that have caught Kirk Franklin and the Winans explaining their motivations to the more sanctified members of the church at times. "I don't criticize because I believe all music was created to praise God and all we're doing is taking back what the devil stole from us and using it to please God."
Dillard says God led him to found the New Generation Chorale in 1988. The next year they won the McDonald's Chicagoland Choir competition. One day he met producer Butch McGee in a parking lot. McGee had heard of him and signed Dillard's group on their reputation alone. New G's first album "The Promise" was released in 1990 and won them a Grammy nomination and a GMWA Excellence award in 1991. The next year the choir was featured in Steve Martin's movie "Leap of Faith." By the time their second live album "A Holy Ghost Take Over" debuted in 1993, Dillard was a consultant on Whoopie Goldberg's "Sister Act II" movie and the choir had appeared on a PBS Television Special "Going Home To Gospel” featuring Patti La Belle and Albertina Walker. In 1994 New G won their first Stellar Award for contemporary choir of the year and recorded all the background vocals for Gospel Queen Albertina Walker's Stellar Award winning album "He Keeps On Blessing Me." "It was a delight to work with the Queen," Dillard laughs just thinking of the experience. "She keeps me laughing." In 1995 New G's third album "Hallelujah" was released and the choir had its first club hit. They collaborated with Frankie Knuckles and Adeva on "Walkin'" from their "Welcome to the Real World'" album. The Virgin Records single became a Top 20 hit on Billboard magazine's club chart.
By 1996 New G had moved to Detroit-based Crystal Rose Records. Their debut "Worked It Out" sold 30,000 pre-orders out of the box. New G had their biggest promotional push yet. The album premiered at Dillard's alma mater before 1,500 screaming students. They capped the push off with a listening party/concert at the Cubby Bear nightclub and a Record Town appearance that rang up almost $10,000 in one day sales. The album quickly jumped to the Billboard gospel top ten and stayed on the chart for months. Then, in 2000 the group leaped back on the charts with the scorcher “No Limit” cd. The single “The Holy Place,” a classic choir vocal with a subtle hip-hop rhythm, buoyed the sales. Beginning back in 1997, the group made their first tour of Europe where they were particularly successful in Germany. "I was surprised that we were so embraced," Dillard says. "But years before I told the choir that we were going to be international and God made that happen for us." Aside from international acclaim, the group has opened for Patti LaBelle and Bonnie Raitt among others. However, wherever they perform, their concert is always “Unplugged…The Way Church Used To Be.”