PIE-O-MY
Of the rare moments of genuine contentment for mafia boss Tony Soprano (James Gandolfini) in David Chase's The Sopranos, I believe it’s in Season 4, Episode 5, that he comes closest to experiencing a fleeting sense of serenity for his tormented soul amidst the betrayal, bloodshed, and chaos that define his world. It's also the most tender we see Tony toward anyone or anything, underscoring the often-noted paradox that even those with antisocial or sadistic personality traits—like Hitler, who was famously affectionate toward animals—can display genuine tenderness in limited, selective ways. In the pilot episode of Season 1, Tony lights up at the arrival of some geese in his swimming pool, which gives him a profound sense of connection. This soft underbelly of Tony's reveals his secret weakness, especially when we sees he's under immense pressure to be the big boss to men who look to him as a leader and fearless to those who see him as an enemy.
Often lamenting the absence of the "Gary Cooper" strong, silent type in modern America, Tony continually seeks to embody a traditional archetype of masculinity—one that he finds nearly impossible to live up to himself, given his overly sensitive nature and his struggles with acute panic attacks.
However, in the episode Pie-O-My, Tony is briefly allowed to channel his inner Gary Cooper or cowboy archetype in a poignant scene where he watches over the ailing horse, Pie-O-My—whom he co-owns with Ralph Cifaretto (Joe Pantoliano)—in her stable, smoking a cigar as the rain pours down outside, joined in quiet solidarity by a sheep.
It also makes perfect sense that Dean Martin and Ricky Martin's duet, "My Rifle, My Pony and Me," from Howard Hawks's western Rio Bravo, accompanies this scene, reminding us of Tony's cowboy dreams.
Compositionally, the final shot of this episode is exquisite—arguably the most deserving of being immortalised in a painting that might hang on Paulie Walnuts’ wall.