Through his company Cinemation Studios, Gaines has produced or financed an extensive number of documentary and narrative films including Da Sweet Blood of Jesus of Spike Lee, the acclaimed Netflix documentary Bill Nye: Science Guy, the remake of Children of the Corn written by Stephen King, and the animated feature The Immortal Warrior starring Rodrigo Santoro for Amazon.

Dubbed as a “superb portrait” by The Hollywood Reporter and Certified Fresh on Rotten Tomatoes, The Lady and the Dale is a genre-bending documentary that traces the audacious story of Elizabeth Carmichael, a larger-than-life automobile executive, who as one of the first openly transgender women, rose to prominence during the 1970s oil crisis with her promotion of a fuel-efficient, three-wheeled car called The Dale.

Featuring talent such as Chris Rock, Dave Chappelle, Kevin Hart, Wanda Sykes, W. Kamau Bell, and Harry Belafonte, the film scored 100% on Rotten Tomatoes, with The Wall Street Journal calling it “a memorable portrait of someone whose story deserves to be better remembered,” and Richard Roeper of the Chicago Sun-Times calling it “rock-solid.” Gaines went on to garner nominations for an NAACP Image Award for Outstanding Directing, an IDA Award for Best Writing, and invitations to lecture at USC School of Cinematic Arts, NYU, Harry Belafonte’s Action Lab, and the Schomburg Center for Research in Black Culture in Harlem.

Alongside executive producers LeBron James and Stanley Nelson, Gaines garnered his second Emmy®-nomination for executive producing and directing the film After Jackie for The History Channel about the heroics of Black ballplayers Curt Flood, Bob Gibson and William White who advanced racial equality in Major League Baseball after Jackie Robinson retired.

The film stars André Holland, Kate Mara, Zazie Beetz, Stephen McKinley Henderson and Aldis Hodge.