4. Miles Davis ('Junk Love,' Season Two)
The jazz legend made his acting debut as the sympathetic smuggler-turned-pimp Ivory Jones in one of the darkest episodes of Miami Vice's five-year run. Davis brought his trademark rasp to the character, who's killed after coming to the aid of a heroin-abusing prostitute attempting to escape an incestuous relationship with her crime-boss father. Davis would appear on screen a few more times before his 1991 passing: the 1987 TV movie On The Edge; a blink-and-you'll-miss-it scene in Bill Murray's Scrooged (1988); the obscure but semi-autobiographical 1991 film Dingo.