Born in New York City and raised in South Central L.A., Gray was already involved in TV while in high school, working at a local cable public access channel. After studying film and TV in college (although never amassing enough credits for a BA), he started his career working the camera for shows produced in L.A. for Black Entertainment Television (BET) and Twentieth Television. Hewing to his career plan, Gray broke into helming music videos, always filming in 35mm, even if it meant taking a lower fee in order to stay on budget. Among the artists for whom he shot videos were Ice Cube, Johnny Gill, Dr. Dre, Mary J. Blige, Tone Loc and Barry White. In 1995, Gray's direction of Coolio's "Fantastic Voyage" earned the Billboard Music Award for Best Rap Video and Best New Artist Video, while Gray's "It Was a Good Day" for Ice Cube was voted "One of the Top 100 Videos of All Time" by Rolling Stone. That same year at the MTV Music Video Awards, Gray's video for TLC's "Waterfall" was voted Video of the Year, and he also walked away with Best Rap Video for Dr. Dre's "Keep Their Heads Ringin'".

After the success of "Set It Off", Gray moved on to helm the actioner "The Negotiator" (1998) which teamed Samuel L Jackson and Kevin Spacey in the story of a hostage mediator who is framed for a murder and takes a group of people as prisoners in order to discover the identity of the real killer. The director had been tapped to steer the as yet untitled sequel to the Eddie Murphy 1996 remake of "The Nutty Professor" but left the project over "creative differences". Instead, he turned his attentions to the small screen as executive producer and director of "Ryan Caulfield: Year One" (Fox, 1999), a short-lived drama about a 19-year-old rookie cop that went through a troubled preproduction and was cancelled after only two airings.

Gray's capable hand guided the Vin Diesel vehicle "A Man Apart" (2003), but it was on his follow-up, the 2003 remake of the heist thriller "The Italian Job" that the director's gifts fully flowered, and he delivered a taughtly paced, well-acted and action-packed crowd-pleaser that landed him on the short list of Hollywood's top creative and commercial directors. Gray firmly proved the extent of his diversity at the helm of the film adaptation of Elmore Leonard's "Be Cool" (2005), the amusing and entertaining sequel to "Get Shorty." Equally deft at handling A-list talent like John Travolta and Harvey Keitel and developing newcomers like Christina Milian and Andre Benjamin, Gray continued his Hollywood winning streak.