Matthew Diamond began his critically acclaimed career as a director and dance choreographer for film and television in the mid-'80s. He began directing episodes of shows like Guiding Light, Designing Women and A Different World before gaining more extensive work directing episodes of Family Ties and Day by Day in the late 1980s. He continued to direct television shows in the early 1990s and even directed 21 episodes of the classic sitcom The Golden Girls before embarking on his crowning artistic achievement later in the decade.

In 1998 he put his experiences as a dance choreographer and television director to good use in the documentary Dancemaker. The documentary was nominated for an Academy Award in 1999 and propelled Diamond's directorial career into the 2000s. He enjoyed further success with dance-inspired programming when he earned heaping critical praise, which included Emmy and Directors Guild Awards, for his work directing Great Performances: Dance in America. He returned to more sitcoms on television afterwards by directing episodes of Scrubs, That's So Raven, and Gilmore Girls. He continued to intertwine dance, music, comedy, and dramatic storytelling with 2008's Camp Rock and, a year later, began directed episodes of the hit reality show So You Think You Can Dance.

Other recent credits include The Wiz Live!, extensive work for Great Performances at the Met and Live from Lincoln Center, and numerous LA Opera simulcasts.