You Should Watch Wiseguy:
The show that changed the face of television while no one was paying attention
If you've ever watched and enjoyed anything that gets tossed around as “prestige television—” you know what I’m talking about— long form narratives, high stakes, actors with something to prove— shows like The Sopranos, Breaking Bad, The Wire, etc.— you have Wiseguy to thank. While largely forgotten by mainstream audiences (for a variety of reasons, including sheer lack of availability), Wiseguy was one of the first non-soap-opera shows with a fully serialized story— one that expected you to see every episode, in order. When it began airing in September of 1987, really the only other thing on TV like it was Michael Mann’s Crime Story (also worth a watch), and Crime Story would be canceled before Wiseguy even hit its second season.
Writers, actors, and industry types of all kinds cite Wiseguy as a major influence— Vince Gilligan and Tom Schnauz credit watching Wiseguy in the 80’s as why they cast Jonathan Banks as Mike— Chris Carter hired writers from Wiseguy when he started the X-Files— actors like Stanley Tucci made their names on the show— and hell, David Chase wrote an angry letter to the New York Times claiming he was absolutely under no circumstances at all influenced by Wiseguy ever, which feels like the kind of thing you don’t need to write a letter about if it’s true.
Of course, just because something is influential doesn’t mean it’s good.
Wiseguy is really damn good.
Much like Miami Vice (and some of the later shows that took influence from Wiseguy), Wiseguy takes the position that there’s very little difference between criminals and the police, and that the justice system is wildly ill-equipped to create justice. Mafia movie blood, with all its inherent moral ambiguity, runs through Wiseguy’s veins, and then after episode nine, it asks you to think about how that blood would pump in a different milieu— corporate espionage and the destabilization of the global south by American capitalists, insular rural politics and the easy rise of small-time dictators, congressional politics and Twelve-Angry-Men-worthy courtroom drama, the music industry and the cutthroat disposal of talented young people. Money and power structures are always suspect, and good-hearted tough guy lead Vinnie is constantly torn between doing his job, doing the right thing, and doing the thing that makes sense to him emotionally.
The show is heartfelt, tense, funny, and above all else, incredibly human. The characters behave irrationally— they self-sabotage, they struggle with moral decisions, they lash out at people they care about— because they’re people, not plot devices. Little things will come back to haunt them, often many episodes later, in believable and sometimes gutting—but rarely shocking— ways. Despite this realism, and a deep sense of cynicism about our institutions, Wiseguy never falls into the trap of wallowing in grim bleakness. The writers and the actors clearly believe in people— it’s a show that says— ‘yeah, the world sucks. So how do we keep going, together?’ The characters are lovable not because they’re all good, but because you feel like you could know them, with realistic flaws and foibles and senses of humor. Sometimes it’s a little silly, and sometimes it’s a little melodramatic— but it works, because sometimes that’s how real life is, too.
Wiseguy is four (well. three and a half) seasons [cross out— and a terrible TV movie that disregards canon], and is notably divided into 4-11 episode arcs within those seasons, and occasional “breather” episodes between arcs. It’s actually a brilliant bit of plotting that I wish more shows would do today— it allows for overarching narratives and real stakes without running into DBZ-like “the next threat has to be BIGGER and MORE DANGEROUS” power level bullshittery that’s common to a lot of long running serialized shows. One of my favorite aspects of this design is that the cast partially rotates every few episodes, but the show still expects you to remember what was going on with the characters from the previous arcs— because they often return later in unexpected and narratively satisfying ways.
The three characters that remain more-or-less consistent throughout the show are Vinnie Terranova, an undercover agent for the Organized Crime Bureau, Frank McPike, his handler, and Dan “Lifeguard” Burroughs, the OCB call-center operator who gives Vinnie field instructions.
Vinnie Terranova is just on the border of thirty when the series begins, a gregarious kid-from-the-neighborhood, just out of a cover-establishing 18-month stint in prison. He is a bundle of contradictions— quick to fall but slow to trust, a practicing Catholic who chose a job in the field of lying and murder, a 50’s hood irritated by bigotry. Vinnie is both far smarter and more sensitive than anyone gives him credit for, which is both his greatest strength and his fatal flaw— empathetic undercover agents burn out fast. He spends a surprising amount of the series trying and failing to quit his job. He has a marshmallow center, a steel-trap mind, and the general affect of your cousin who dropped out of college to marry his pregnant high school sweetheart. He also has no idea that his type is “angry asshole” and keeps being surprised when he falls for them.
Frank McPike is a curmudgeon's curmudgeon, a career fed with a chip on his shoulder, a fathoms-deep sense of cynicism, and a collapsing marriage. He and Vinnie begin the series at odds, and as you watch the first few episodes, you're going to seriously struggle to believe me when I say that the affection between Frank and Vinnie becomes the absolute thematic and emotional heart of the series. Frank is also a genuine oddball failing to pose as a tough guy; he makes noises, he lurks in strange costumes, and the words he chooses when he’s irritated beggar normal human understanding.
We don’t get to know Dan as quickly or as deeply as we get to know Vinnie and Frank (in fact, he’s introduced as “Mike”), but he’s the man behind the curtain, a guiding moral and emotional star for Vinnie, a talented musician, and a cheerful face with a lot of anger bubbling just below the surface. He offers life advice even as his own home life is in constant meltdown, and loves both Vinnie and Frank with a fierce, sarcastic weariness. Dan is also an amputee, and his disability is portrayed with respect and without pity— a rarity for television even now, but especially in 1988.
You’ll absolutely fall in love with these three, but one of the things that makes Wiseguy so special is its fantastic supporting cast. The world is fleshed out and lived in, and you get the distinct sense that all the recurring characters have their own lives we don’t get to see off screen. There’s Carlotta— Vinnie’s mother, as contradictory and sharp as her son, Pete— Vinnie’s brother, a progressive basketball-playing priest, Roger Lococco— a killer-for-hire who refers to every person on the planet as Buckwheat, Rudy Aiuppo— an elderly don with the heart of a trickster spirit, and a whole host of others who enter and exit the narrative throughout the arcs of the show. There are also a whole host of wonderful arc-based characters played by incredible actors, journeymen and and famous alike— including turns from Tim Curry, Debbie Harry, Jerry Lewis, Stanley Tucci, Patti D’Arbanville, Stephen Bauer, and Billy Dee Williams. You can tell everyone involved in the show had a fantastic time working on it, and nearly every actor who comes aboard really puts their whole Wisegussy into it gives it their all.
You notice that as I’ve been speaking, the lights have dimmed slightly, and the strains of an organetto have started to play quietly in the background. A man in a rumpled suit is smoking nearby, though you are fairly certain smoking indoors hasn’t been legal in a number of years. I pass you a plate of espresso and biscotti.
Let’s talk arcs.
The first arc of the show, known as the Steelgrave arc, is a lot of fans’ favorite arc of the show, and for good reason. Vinnie infiltrates a New Jersey mob organization, and gets very, very close* to this man:
Sonny Steelgrave, human Knife Cat, is a complicated man, and Vinnie has complicated feelings about him. He’s very nearly a co-protagonist to Vinnie in this arc, and the show artfully toes the line between condemning him and making it clear that he’s not always entirely wrong. Vinnie’s goal is to get Sonny into prison and take down the entire family— how and whether he achieves this goal is best left unspoiled. Sonny may not have been the first complicated, likable villain on television, but his arc is intense, heart-wrenching, and splendidly morally grey. I don’t think it’s an overstatement to say that the Steelgrave arc is the best nine hour mob movie ever aired on television.
*I’m really not kidding about the closeness. There’s an episode where Sonny announces he’s getting married and literally all the other mobsters are like ‘oh, now I understand why Vinnie has been in a bad mood all day.’ They are as close to canonically in love as a federal agent and a mobster have ever been portrayed on screen.
Lest you get Kevin-Spacey-jumpscared, the following arc unfortunately has Kevin Spacey in it. Thankfully he plays a slimy sister-kissing coked-up hypercapitalist, so it’s fairly easy to just hate his character in the same way you hate the actor and move on with your life.
This arc, the Profitt arc— in which Vinnie is tasked with taking down a wealthy business mogul who is suspected of drug-and-gun-running— is, for many fans, a close second to the Steelgrave arc. It’s an interesting change of tone and locale, and introduces Roger Lococco, who is a really stellar supporting character. Personally, I rank a bunch of other arcs above Profitt, because no matter how much I like Roger, Mel and Susan are bananas, and they wear out their welcome before they exit the narrative. Regardless, it’s a stylish arc— one that rather kicks truth, justice, and the American way in the teeth— and Mel’s machinations have serious reverberations later in the show. The Roger subplot is also genuinely excellent, and good old Corey Matthews’ Dad plays him with aplomb.
Back home, after trying to quit his job and failing, Vinnie has to deal with a threat with much smaller, but far more personal stakes. A white supremacy group has moved into his neighborhood and is attempting to recruit working-class Italians to their cause, pitting an older immigrant group against a newer one, pitting Catholics against Jews, and pitting a previously “ethnic” group’s newly acquired “whiteness” against people of color. I have mixed feelings about the Pilgrims of Promise/White Supremacy arc, because it’s truly quite good, and it pulls no punches about the kind of people fascists are and prey on, but it’s also exceptionally fucking upsetting that nothing has changed at all since 1988. Literally you could remake this arc word for word today and a) it would be exactly as believable, and b) your show would be immediately boycotted and canceled for being too “woke.” Great writing, great stakes, great character motivation; so, so uncomfortable to watch.
And then Ken Wahl breaks his leg in real life, and they have to replace him for a few weeks.
The Garment Trade arc starts off pretty promising— Vinnie meets with the son of a clothing manufacturer, they have great (borderline meet-cute) chemistry, it’s a wonderfully New-York-in-the-80’s kind of storyline, Jerry Lewis is there, and I think it’s the only time I’ve ever seen Sukkot represented on TV— and then Vinnie has to leave for the next four episodes because of Wahl’s broken leg. They rewrote the arc on the fly, and considering that, it’s pretty good. Jerry Lewis is still there, and he gives the serious, dramatic performance of a lifetime, and Stanley Tucci chews scenery as The World’s Slimiest Businessman. We meet Vinnie’s childhood bestie, “Mooch,” whose actor, delightfully, starred beside Ken Wahl in 1979’s The Wanderers. My beautiful and talented wife Joan Chen even shows up for an episode. However, all of this is undercut by the lack of Vinnie; his replacement, a semi-retired agent named Raglin, is… a bit milquetoast. He’s okay, and he’s given some interesting backstory in his final episode, but he’s no Vinnie.
Once again sporting a functional leg, Vinnie returns, and my favorite arc other than Steelgrave follows.
In the Dead Dog arc, Vinnie has to pose as a music producer, because the OCB traded an airplane for a music label. It’s the dumbest, most fantastic plot device of all time, and brings me incalculable joy. I literally made Dead Dog t-shirts because I love this stupid fake music label owned by a fictional government agency so much.
The Dead Dog arc sees Vinnie at his happiest (the poor man really, really just wants to quit undercover work and stop being involved with Murder Organizations), and the crime he’s investigating is… wait for it… bootleg CDs. You would think this would be a ridiculously boring premise for an investigation, but the Dead Dog arc has Tim Curry, Debbie Harry, Glenn Frey, and Patty D’Arbanville playing a cadre of unhinged music industry moguls all attempting to stab each other in the back, and it is exactly as chaotic as you would expect based on that cast. This arc also had a bunch of original music produced for it, which is extremely fucking cool, except that then the studio lost the rights to the music it created and this arc became inaccessible and unwatchable except through circulating the tapes, so to speak, of early 90’s TV rips. (The irony is not lost on me that the arc about the Evils of Piracy is the arc that one must pirate.) Miraculously, in the last year, Wiseguy’s rights have been renegotiated, and the newest sets of the show have Dead Dog restored. Accessibility via streaming is still a bit of a mixed bag— the episodes were streaming on Tubi and Youtube briefly, but now appear to have been taken down again.
After his turn as a surprisingly successful music producer, Vinnie returns to his roots: the mob. In the Mob Wars/Trash Wars arc, Vinnie unintentionally becomes the temporary leader of the local mafia commission (I will not spoil how.) The OCB wants to use this as an opportunity to take down the entire organization from the inside out, and Vinnie must deal with mafia backstabbing, pressure from Frank and the OCB, and surprisingly personal stakes. It’s an unspectacular but solid arc that regrounds the series, and the interpersonal aspects of the story— and its examination of fathers and sons and generational inheritance of social rules and expectations— are excellent. The Mafia Wars storyline won’t blow your pants off, but it’s thoughtful and well-executed and reminds us of who Vinnie is and where he came from.
What follows is another of my favorite arcs, referred to as the DC or Counterfeit Yen arc, but perhaps better described as the Mr. Terranova Goes to Washington arc. Vinnie is summoned by the federal government to investigate counterfeiting, and thus unfolds a multinational conspiracy that ties back to the Profitt arc. Much like the White Supremacy arc, this arc is distressingly current— Vinnie is a patsy for a group of corrupt republican senators who want to destabilize the currency of a perceived East Asian economic rival. It’s Yen here, but all you’d need to do to bring this arc into 2023 is swap out references to Japan for China, because the American government has changed very little from the 80’s and has to be awful about some country somewhere or, I don’t know, a bunch of horrible old racist politicians will shit themselves. Vinnie enters talking like Jimmy Stewart, and leaves with one more thing to be crushed and disillusioned about. We get some riveting and stomach-churning courtroom drama, the bad guy turns out to be capitalism all along, and Frank threatens to shoot a Howard Hughes stand-in on a ski lift.
And then somehow we end up in Twin Peaks. The Lynchboro arc predates Twin Peaks by a whopping two months, indicating a total coincidence of premise similarities, but it does take place in a corrupt rural Pacific Northwest town unduly influenced by one large family/company, wherein an outsider has to investigate a tangled conspiracy and deal with strange townsfolk and some spooky happenings. There’s no way either show could’ve plagiarized the other— they were assuredly written and in production at the same time— but it is deeply bizarre. In the Lynchboro arc, Vinnie goes undercover as a local beat cop, and finds himself faced with both a serial killer and a land-rights and building-contracts espionage plot. He also has to deal with Mark Volchek, the ostensible “owner” of the town, and his eccentricity and decreasing grip on reality. Roger returns, and Vinnie must finally confront the enormity of his trauma. One major character is literally brought back from the edge of death by another character’s crushing love for them, expressed via church bells. It doesn’t exactly end on a cliffhanger, but it doesn’t not, either.
And then Ken Wahl quit.
Season Four begins with a deeply depressed, heavily bearded Frank struggling to find the will to live after Vinnie has disappeared. (I don’t think I’m really at risk of spoiling anything serious by saying that we are “supposed” to think Vinnie is permanently gone, but that there are a huge number of blatantly spotlighted contradictions in that story. Wahl left on decent terms, and I firmly believe the Wiseguy staff was expecting to eventually win him back to the show and have his absence turn out to be a ruse. Unfortunately, Wiseguy got cancelled before this could happen.) Frank spends the first (and only complete) arc of this season investigating his partner’s disappearance, eventually working with the supposedly-corrupt DA who helped establish Vinnie’s cover back before Season One.
It’s not an uncommon opinion to say, ‘hey, just skip S4’— and honestly, if you chose to watch S1-3, you’d have consumed a wonderful story with a reasonably coherent ending. But I don’t actually hate Season Four. The “new Vinnie—” Michael Santana, played by pretty-boy Scarface alum Stephen Bauer— is exceptionally likeable, and he brings with him a new set of characters who are also quite compelling. Furthermore, if you’re a Frank fan, he really gets the spotlight in this season, and if you’re a Frank/Vinnie fan, Vinnie may not be around, but Frank’s despair is really fucking something else. It’s almost worth it just to see him lie to the FBI and tell them he “never crossed the line” of professionalism with Vinnie.
Unfortunately, the next arc sets up something really compelling and unique, but it’s only 3 (unaired on TV) episodes, and ends on a complete cliffhanger, because the show was unceremoniously cancelled. After his niece is shot in the midst of teenage gang violence, Michael teams up with Billy Dee Lando Calrissian Fucking Williams to investigate red-lining and racist underfunding of schools. Oliver Stone shows up in the last like, ten minutes of the last episode?? I would be all over this storyline if it wasn’t just dropped like a moldy tomato, but I guess that’s what fanfiction is for. It’s not how Wiseguy deserved to go out, but hey, it was really aiming for the stars even as the plug got pulled.
Oh, and if anyone tells you there’s a 1996 TV movie, no, there isn’t.*
(*The movie is so deeply mediocre that it’s worse than any of the controversy surrounding Season Four. It essentially retcons all of S4 and, frankly, really the last few episodes of S3, and presents a bland, uninspired “getting the gang back together” story that retreads thematic materials from the show without saying anything new. Vinnie has apparently been doing wiretapping for 6 years, which is completely at odds with everything we know about his character, and he and Frank are treated as “dinosaurs” that the OCB doesn’t know what to do with, and yet they are also simultaneously the only ones who can take care of a nearly-kidnapped child. It’s rushed, it’s emotionally hollow, the actors are phoning it in, and it ignores all of the character development from the series in a way that renders its plot nearly nonsensical. Furthermore, Ken Wahl had been in a seriously disabling motorcycle accident a few years before, so his apparent discomfort and stiffness throughout the film is because he’s genuinely in significant pain. Don’t watch the movie. You can always write fix-it fic for how Vinnie manages to come back after Season Four. It’s much harder to write fix-it fic for boring character assassination written by the 'due-process-is-for-pussies-and-torture-works' 24 guy.)
One of the other delightful things about Wiseguy is that Vinnie is both a big softie and yet is also saddled with a bizarre sort of erotic smolder, and therefore he has ridiculous chemistry with basically half the cast of the show. Vinnie very much seems a guy like you could say some blandly nice things to and buy him dinner, and you’d wake up, exhausted and satisfied, the next morning to him cooking breakfast. You’d think, wow, this guy is so thoughtful, he must be the one— and then you’d turn your head and he’d have immediately been seduced by the next schmuck down the line. He’s a good boy, but his “acceptable romantic target” sensors are so wildly mistuned as to render him, affectionately, a tragic slut. Will he end up with a mobster? One of a number of widows? His boss? No one knows but god.
Vinnie is also heavily bi-coded— his relationship with Sonny is almost explicitly romantic, he calls out Roger for homophobia (in 1989), one of his old friend asks if the reason he’s not married is because he ‘likes boys,’ and he doesn’t say no, and he has a borderline I-love-you moment with Frank. The boy just wants someone to love him, goddammit.
I’m also really not kidding about Vinnie and Frank developing into the emotional core of the series. They live together for a period of time. They both imply they can’t live without the other. They go shopping for Dan’s birthday together. They pick up Frank’s ailing father from the nursing home together. Frank picks out Vinnie’s tie.
You pick at the plate of spaghetti that appeared in front of you, unsure of either its provenance or why it came after dessert. It’s the best spaghetti you’ve ever had, and that frightens you, somehow.
I lean in close to whisper to you about crime. You note that at some point I changed into a pinstriped suit. You don’t remember me changing, or even getting up— you console yourself with the notion that maybe I’d been wearing it from the start, even though you know that isn’t true.
So, the thing about Wiseguy is— well— it’s more available than it used to be. The whole series was recently released on blu-ray, and both that set and the most recent DVD sets actually have every episode, a change from the previous releases. As of August 2023, all of the series except Dead Dog is available, legally, on Youtube. This is a vast improvement from even two or three years ago, when multiple episodes weren’t available through any means but blurry, VHS-tracking-laden downloads of TV rips.
Unfortunately, the most recent renegotiation of the series home video and streaming rights still failed on the music rights front. Dead Dog has been spared the hammer, but there are still places where the series has gaps. Notably, there’s an episode (Stairway to Heaven) where Frank murders a jukebox, and looks completely fucking insane, because the original (thematically meaningful) music the jukebox was playing was replaced with generic elevator music. Worse, the final episode of the Steelgrave arc (No One Gets Out of Here Alive) is missing two musical cues: in one instance, Sonny himself is singing, in a fit of mania, and the footage has straight up been cut from the episode because they couldn’t get the rights to The Young Rascals’ Good Lovin’. Equally egregious, The Moody Blues’ Nights in White Satin, which originally played over nearly a minute of sustained, silent eye contact between Sonny and Vinnie— has been replaced with the Wiseguy opening theme. It renders a scene which should be quite clearly devastating and unsubtly romantic instead utterly awkward and bizarre. It’s hard to demonstrate just how jarring the change is unless you’ve seen the scene, but suffice to say that everyone I know who has seen both versions— in either order— has expressed horror and bafflement at the substitution.
Which is to say: there’s a couple of episodes of Wiseguy you’re probably going to want to locate those shitty old TV rips of. It’s worth it, even if it seems like it wouldn’t be.
I place my hand over yours. You jump a little. I have a number of large, dark-stoned signet rings, and my hand is strangely cold.
I make you an offer you can’t refuse.
You’re going to watch Wiseguy.
