* SugarWiki/AwesomeMusic: Del Shannon's updated version of "Runaway" used as the credits music, which went so far as giving him a CareerResurrection.
* DirectorDisplacement: As with ''Series/MiamiVice'', Creator/MichaelMann was a producer and main creative force, but didn't create the series, though he did direct at least one episode.
* HarsherInHindsight:
** In one episode, Creator/KevinSpacey played a Senator in danger of becoming embroiled in a sex scandal. In 2017, Spacey's career started becoming derailed by accusations of sexual misconduct.
** Former Chicago jewel thief John Santucci, who played Ray Luca's dumb-but-lovable flunky Pauli Taglia and whose acting career started in Michael Mann's ''Film/{{Thief}}'' along with Dennis Farina (his former Chicago PD arresting officer), fell back into his previous criminal life and was arrested in Chicago in 1994.
* RetroactiveRecognition:
** Creator/DavidCaruso appeared as Johnny O'Donnel, a friend of Ray Luca, in the pilot (episodes 1 and 2). He appeared in flashback scenes in episode 12, and in episode 19 of the second season.
** Creator/JuliaRoberts appeared as a juvenile rape victim in the Season 1 episode "The Survivor". It was her first TV appearance.
** Creator/KevinSpacey appeared in second-season premiere as a crusading, Kennedy-esque Senator. This was his first major television appearance.
** Creator/VingRhames appeared in the season 1 episode "Abrams For The Defense" as Hector Lincoln, a husband and father accused of assaulting his landlord. This was his second television appearance.
** Creator/ChristianSlater played a teenager who discovered a body in "Old Friends, Dead Ends".
** Creator/MichaelRooker appeared as a uniformed police officer in the pilot's opening.
** Creator/LorraineBracco appeared as a woman held hostage by a gunman in a season 1 episode.
** Creator/LauraSanGiacomo as the wife of a protected witness in "Protective Witness".
** Creator/GarySinise as a member of a gang of thieves in "For Love or Money". He also directed the episodes "Fatal Crossroads" and "Torello On Trial".
** Creator/EliasKoteas as a fugitive that Torello is chasing through the desert in "Sidewinder".
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