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After decades of success in the music business, Frankie Valli wanted to stretch out and try something new. For the singer of No. 1 hits such as “Sherry” and “My Eyes Adored You,” that meant trying his hand at screen acting. And Valli got started in style on an episode of Miami Vice.

When Valli made his guest-star appearance on the show in 1985, Miami Vice was near the peak of its popularity. At the end of that season, executive producer Michael Mann would leave, and the show would begin to slump in the ratings.

But when Valli appeared in Vice, it was being called the hottest show on TV with good reason. From there, Valli continued working as an actor until he hit his screen-acting peak on season 5 of The Sopranos.

Frankie Valli played a mob associate in a season 2 episode of ‘Miami Vice’

Frankie Valli  sits on a couch in a dark suit and white tie as Frank Doss in 'Miami Vice'
MIAMI VICE, “Buddies”: Frankie Valli as Frank Doss | NBCUniversal via Getty Images

The Miami Vice installment “Buddies” (season 2 episode 5) starts off with a character played by guest star James Remar (48 Hrs., The Warriors) spinning out of control. Robbie Cann (Remar) is an old war buddy of Sonny Crockett (Don Johnson), and the audience quickly learns that Cann’s related to a Miami mobster.

That thread leads to Valli’s character Frank Doss, a top figure in a crime organization run by Cann’s uncle (played by Tom Signorelli). While the episode’s plot gets convoluted, the bottom line is Valli’s character has a problem that only a murder can solve. And he has some scenes setting that up.

As in so many other Miami Vice episodes, the narrative matters less than the shootouts and climactic car chase (the streetlights reflecting off the hood of Crockett’s Ferrari, of course). And the nightclub world of “Buddies” is where the conflict of the episode arises.

That places Valli in a world he knows all too well. The audience sees him (as Doss) size up the act of a comedian (played by guest star Nathan Lane) and cringe as a cocktail waitress can’t handle her job. Valli doesn’t seem entirely comfortable on-screen as Doss, but the role represented a solid start for him.

Valli landed other film and TV roles prior to his ‘Sopranos’ appearances

Frankie Valli and Joe Pesci smile and pose for the camera
Frankie Valli of The Four Seasons and Joe Pesci | KMazur/WireImage for Tony Awards Productions
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Valli’s acting career didn’t exactly take off after Miami Vice, but he did appear in two productions in ’87. In the ’90s, Valli kept making appearances on-screen while he released a new album with the Four Seasons (1992’s Hope and Glory).

Then Valli played Frank LoCascio in Witness to the Mob (1998), a Robert De Niro-produced TV movie that featured a number of Sopranos stars (including Frank Vincent, Michael Imperioli, Vincent Pastore, and Tony Sirico).

Once The Sopranos hit, Valli tried out for the role of Beansie Gaeta in season 2, but David Chase didn’t think he’d work as the character. (Paul Herman played Beansie in the end.) Yet Chase didn’t forget Valli, a true New Jersey legend. In season 5, he brought Valli aboard as Lupertazzi capo Rusty Millio.