Introducing Antihero #4 — Tony Soprano. Where to begin? Not only are the Sopranos my favorite painting companions, the late James Gandolfini’s portrayal of Tony is one of the great character turns in history. I’ve watched the series start-to-finish ten times, and will continue to do so for years.

How do you choose one iconic moment over six incredible seasons? I decided to use this snap from Season 1 Episode 5, when Tony is sitting in the lobby of the college Meadow is visiting, looking upward toward the Hawthorne quote, “No man can wear one face to himself and another to the multitude without finally getting bewildered as to which may be true”.

This episode, particularly the moment Tony strangles the rat, is considered the breakthrough moment of TV’s Second Golden Age. Beyond that, I didn’t want to portray the gangster puffing a cigar everyone expected to see. Rather, this is part Gandolfini’s 260 pound Woody Allen coupled with Soprano’s idea of himself as the sad clown. Not to be too heavy here, but there is also an element of St. Sebastian (famously re-envisioned on the cover of Esquire with Ali) — certainly intentional by the amazing David Chase.

The quote Tony is staring at in the source image… moments after taking a mans life. He is visually taking inventory of his life. A powerful moment.

Over the years, I’ve made sense of this collage style… here is the placement map pre-headline application.

A sea of NY Post Headlines ready-to-go… the content speaks for itself.

Fully collaged… in his shirt, there are two images of Gary Cooper, the strong silent type, an Italian American deli from the 40’s, a snippet of Coney Island, the view from Jersey to NY, Gotti headlines, and a Warhol Soup Can, famously roasted by Tony when he said to Carmela, “what, you’d rather she be in the city looking at pictures of Soup Cans?”

Red background for an underpainting… carving-in with the shadows.

I wanted to challenge myself with the palette, so I explored a blue/green and deep red combination.

This is not the same background as in the scene, rather I created a new one featuring leaves intermingling with flying ducks… for fellow Sopranos’ nuts, you’ll know what those ducks are all about.

Lime green and electric blue…

Ah, that moment when it begins to come together… I work dark-to-light, and back again.

Throwing everything into turmoil… muddy here, but the foundation is there.

Pink was a risky choice, but I felt if properly accompanied it would work.

Beginning to make sense of the facial tones… carefully creating new planes.

Down to the final decisions.

And I give you: Tony Soprano. It was quite a journey… more emotional than I expected it would be. Thank you James Gandolfini for breathing life into this character, and thank you David Chase for creating The Sopranos. For those keeping score at home… it took me five complete seasons to paint this.