Wiseguy: An Innovative TV Crime Drama

If you love shows like Breaking Bad, The Wire, or The Sopranos, you owe a debt of thanks to a lesser-known series from the late 1980s that showcased serialized storytelling before it was the norm on television. That show is Wiseguy, a bold, ahead-of-its-time crime drama that helped shape the future of television storytelling. Premiering in 1987 on CBS, Wiseguy challenged viewers by breaking the mold for episodic television. Instead of wrapping up its stories in self-contained 45-minute tales every week, Wiseguy featured long-form story arcs that unfolded over multiple episodes.

Wiseguy told the story of Vincent “Vinnie” Terranova (Ken Wahl), an undercover agent for the fictional Organized Crime Bureau. After serving 18 months in prison to establish his cover, Vinnie is assigned to infiltrate various criminal enterprises while reporting to his gruff but loyal handler Frank McPike, portrayed by Jonathan Banks, whose chemistry with Wahl was one of the highlights of the show. Banks, who later played Mike Ehrmantraut on Breaking Bad, steals as many scenes in Wiseguy as he would on that later series. 

The series was created by Stephen J. Cannell and Frank Lupo. At the time, Cannell was best-known for action-heavy fare like The A-Team, and several networks turned down Wiseguy before CBS a=took a gamble on the series. What sets Wiseguy apart isn’t just the undercover drama or the mob intrigue—it’s the emotional and psychological toll that comes with living a lie. Vinnie isn’t some slick, invincible hero. His missions are complicated not only by the inherent dangers of deep cover work, but also by his own moral struggles and the personal toll of living a double life. For example, Vinnie can't tell his mother about his undercover status, so she thinks he's a real criminal, and has shut him out of her life. Wahl does an excellent job in the series, conveying Vinnie's internal conflicts and emotional turmoil.

Ken Wahl in Wiseguy

The show’s first major storyline—the “Steelgrave Arc”—is still considered one of its finest. Over nine episodes, Vinnie embeds himself into the Atlantic City mafia and becomes close to Sonny Steelgrave, a volatile but charismatic mob boss masterfully portrayed by Ray Sharkey. What makes the story so compelling is that a real emotional bond forms between Vinnie and Sonny. The undercover operative begins to genuinely care about the man he’s supposed to bring down. It’s a relationship built on lies, loyalty, and looming betrayal—and it all leads to a devastating, unforgettable conclusion.

In today’s television landscape, complex relationships like that are the norm. But back in 1987, that kind of emotional storytelling—spread across multiple episodes with real consequences—was revolutionary. The series would continue to offer long form multi-episode arcs across its four-season run, featuring actors like Kevin Spacey, Jerry Lewis, Tim Curry, Ron Silver and Deborah Harry in later story lines. Rounding out the supporting cast, Jim Byrnes portrayed Lifeguard, Vinnie's OCB contact, Gerald Anthony played Vinnie's brother Pete, a Catholic priest, and Elsa Raven appeared as Vinnie's mother, Carlotta.

Though the series was eventually derailed by cast changes, behind the scenes drama, and network meddling, its influence lingers. Shows like The X-Files, NYPD Blue later blended procedural formats with ongoing character development, but Wiseguy was doing it years before it became the industry standard. It was a gritty, ambitious series that re-imagined what serialized storytelling could look like on network TV. If you’re a fan of deeply layered crime dramas, it’s worth going back to see where it all began. Wiseguy is currently streaming on Peacock.