Wiseguy

A U.S. television series centered around Vincent "Vinnie" Terranova (played by actor Ken Wahl), an undercover agent for the OCB (Organized Crime Bureau), a fictional division of the FBI. A major theme was the constant ethical dilemmas faced by the protagonist, who had to befriend criminals with the eventual intention of betraying them.

Created by veteran hit producer Stephen J. Cannell, Wiseguy veered from the traditional "bad guy of the week" Police Procedural by breaking the drama into multi-episode Story Arcs that followed an infiltration -- and its charismatic criminal target -- to its logical conclusion, no matter the cost to criminal, innocent civilian, or cop (though there were standalone Breather Episodes in later seasons, mostly dealing with the personal lives of the characters). The show influenced writers like Chris Carter, Joss Whedon, and David Simon to build on the trope of showing both sides of the morality play in humanizing detail.

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Tropes used in Wiseguy include:

• Arms Dealer: Mel Profitt, although his drug business gets more attention.
• Audit Threat: In the Eli Sternberg arc, McPike is trying to get some information from a company that does business with the group that they are investigating. They refuse, until McPike says "If you don't let me in, I will call my friends at the IRS. They eat guys like you for breakfast." The company lets him in immediately.
• Becoming the Mask: Vinnie's OCB handler Frank McPike often has to remind him that his job is to lock up the bad guys, not be their friend. It doesn't help that Vinnie is regarded as a trusted associate by the criminals, and a scumbag lowlife by the police.
• Big Brother Is Employing You: McPike has a tendency to bug any place Vinnie is likely to be. Played for laughs when Vinnie is in bed with his Love Interest Amber Twine.

Amber: "Aren't you going to tell McPike about this?"
Vinnie: "Don't you know? McPike's already listening (shouts at bedstead) HEY MCPIKE!"

• Career Killer: Roger Loccoco who turns out to be a Deep-Cover Agent for the CIA.
• The Cartel: Cuban-American crime lord Armando Guzman, investigated by Vinnie's replacement Michael Santana.
• Conveniently Unverifiable Cover Story: Averted as Vinnie uses his own identity, including an eighteen-month prison sentence to establish his credentials as a criminal. Unfortunately this alienates him from his own mother, who doesn't know he's a federal agent.
• Corrupt Corporate Executive: Music industry mogul Winston Newquay (played with villainous relish by Tim Curry). Some of the highly-educated next generation of mafiosi also qualify, such as Rick Pinzolo in the Garment Trade arc.
• Evil Duo: International Arms Dealer Mel Profitt and his sister Susan. As teens they killed their foster brother (by hanging him upside down until he passed out, then throwing him in the swimming pool) when he found out about their incestuous relationship. Together they form a "psychotic critical mass", as McPike describes it.
• Faking the Dead: Roger Loccoco. Also the prosecutor Vinnie 'kills' to prove himself to Sonny, though an ambitious prosecutor willing to hide for years just to uphold an agent's cover is a bit unlikely.
• Government Conspiracy: A secret group within the Washington D.C. hierarchy plans to use Mel Profitt to finance a coup against a communist regime in the Caribbean. When Vinnie causes this plan to fail they frame him as the mastermind behind another conspiracy to destabilize the Japanese economy with counterfeit yen.
• Hammerspace: In the first episode, The Mafia is surprised to see an Arms Dealer bring a woman to their meeting. As things go badly we see her casually unbuttoning her skirt (how she does this without attracting attention is not explained), then she somehow produces an Ingram MAC-10 and starts blazing away. Now admittedly, the MAC-10 is quite small for an SMG, but it's still a large chunk of metal to be hiding between your legs while wearing a tight skirt. It's worth noting that this was based on a scene in The Underground Empire where the narrator noticed two women at an arms deal were concealing firearms between their legs just from the way they sat down.
• Hauled Before a Senate Subcommittee: Happens twice to Vinnie regarding the above conspiracies; first as a witness, then as a suspect.
• Heroic BSOD: Vinnie considers resigning after his first target (Atlantic City mob boss Sonny Steelgrave) commits suicide rather than face prison; when the suicide of another target reminds him of this event, he suffers a complete breakdown and flees the OCB. The protagonist of the Garment Trade Arc, retired agent John Henry Raglin, suffers PTSD from an earlier case where two whistle-blowers were murdered.
• Identical Grandson: Vinnie Terranova's dad (in an episode based around his father's diary). But they gave him a mustache.
• If You're So Evil Eat This Kitten: In the first episode, Sonny Steelgrave, already partly suspicious of Vinnie, declares the only way he can prove himself is to shoot a prosecutor who's been hounding him.
• Incredibly Lame Pun: After loan shark Johnny "Coke Bottles" (for his thick glasses) is Driven to Suicide, the next day's headline reads "Bottles Cashes In".
• Initiation Ceremony: Played for humor when Vinnie becomes a made man -- Sonny thinks it's no longer relevant in this day and age, while none of the old-time mobsters can agree on what the correct procedure is.
• Madness Mantra: Mel Profitt's "Only the toes, knows".
• The Mafia: Sonny Steelgrave, Garment Trade and Mafia War arcs.
• Mission Control: Daniel Burroughs, AKA "Lifeguard", a disabled agent who communicates mostly via telephone (posing as Vinnie's "Uncle Mike"). Vinnie calls him daily to pass on and receive information; he also has codewords for when he's in trouble.
• Pet the Dog: Most villains have these moments at one time or another, leading to Wangst on the part of the hero. It's Vinnie's own mother who points out that Adolf Hitler and Attila the Hun had moments of genuine compassion too, but that didn't offset the evil that they did.
• Racist Villains: Knox Pooley and his follower Calvin Hollis, leaders of the white supremacist group Pilgrims of Promise. Pooley turns out to be a Con Man just in it for the money, while Hollis suffers a Villainous Breakdown after Pooley rejects him.
• Ripped from the Headlines: The Mel Profitt arc (and the pilot episode where Sonny Steelgrave gets into a hotel gunfight with a weapons dealer) draws from the non-fiction Doorstopper The Underground Empire by James Mills. The eccentric billionaire in the Counterfeit Yen arc is clearly inspired by Howard Hughes.
• Scary Black Man: The machete-wielding ex-Ton Ton Macoute boss in the Guzman arc. When he makes the fatal mistake of insulting Guzman's manhood, however...
  • Hilariously subverted when music mogul Newquay is locked up in a cell with a Scary Black Man who's twice as big as he is. Newquay clearly fears the worst, only to have his fellow inmate join him in an enthusiastic duet of "Soul Man".
• Schrodingers Cat: Ken Wahl returned for a reunion movie in 1996, with no explanation of what happened to him in the Guzman arc.
• Suspiciously Similar Substitute: After Ken Wahl broke his ankle in an on-set accident, he was replaced by Anthony Denison (playing John Henry Raglin). This was Written in Infirmity as Vinnie having his leg broken by loan-shark Johnny "Coke Bottles". After a dispute with the producers Ken Wahl was replaced by actor Steven Bauer, playing disbarred Cuban-American prosecutor Michael Santana. Vinnie had ostensibly been killed by a death squad while investigating the smuggling of Salvadorean refugees.
• Town with a Dark Secret: Lynchboro, Seattle; run as the personal fiefdom of Mark Volchek and unknown to him, harboring a Serial Killer. It turns out that Volchek is actually an Ineffectual Sympathetic Villain. He suffers from a phobia of death, so intends to build a cyrogenic storage hospital for the entire town so no-one will ever die. Frank McPike and Roger Loccoco snap him out of it though.
• Trouble Entendre: Mark Volchek orders Vinnie to "get rid" of a teenager who tried to shoot him, and is shocked when Vinnie returns with a jar supposedly containing the boy's ashes. They decide on a codeword to avoid future "misunderstandings".
• Vigilante Man: After white supremacists murder his brother Pete (a Catholic priest), Vinnie considers killing the man responsible. Vinnie eventually decides to bring him to justice only for the villain to be killed in custody by local police for his role in the death of a black officer.