Jackie’s Back (1999)

This silly mockumentary chronicles the career of Jackie Washington, played by Jenifer Lewis, a Diana Ross-like diva, who rose to fame as a singer in an all girls group and is now launching a spectacular comeback concert. It’s a bit rough on the edges, being a made for cable TV film, but it makes up for it with the astounding number of cameos, celebrities either portraying versions of themselves or as fictional characters. Lewis thoroughly embraces the role in all her full-throttle divaness. As with The Five Heartbeats, director Robert Townsend really has an eye for portraying realistic tales of early R&B characters.