![]() This unassuming, bratty sister of Tony’s is a mainstay of Season 2 and becomes increasingly shrewd throughout the show's run. It’s a testament to the acting chops of Aida Turturro that Janice Soprano is one of the most hate-able characters in a show chock-full of unsympathetic, cold-blooded murderers. Even worse, Vito was married to Phil’s cousin, Marie, crushing her and mentally scarring her kids for life, to which Phil doesn’t even bat an eye. His slaying of Vito is one of the ugliest in the series, a hate crime of such unspeakable cruelty that would make any crime-drama aficionado shudder. Yet, in a world where intolerance is a given, Phil’s bigotry shocks even his nastiest peers. He’s stubborn, misogynistic, violent, and arrogant, but that’s par for the course in the underworld. Phil isn’t much worse than the average capo or boss in The Sopranos. Phil serves Johnny Sack ( Vincent Curatola), patiently waits to strike, then orders hits on his colleagues to take the top spot in his crew, becoming the ultimate "Big Bad" of the final season. Leotardo enters the fray when he’s released from prison as part of the “Class of ‘04”, along with mad-dog Feech La Manna ( Robert Loggia) and Tony Blundetto ( Steve Buscemi). Phil Leotardo is an ambitious capo played by crime-movie legend Frank Vincent. out, who knows what kinds of wretched misdeeds he would have gotten into. He holds up a mob-run card game, bungles it miserably, carjacks a lady, then leaves his friend behind to be murdered by Christopher Moltisanti ( Michael Imperioli). After Meadow dumps him, Jackie’s recklessness peaks. His disrespect for Meadow awakens the parental instincts in viewers, who feel protective of one of the few genuinely nice characters in the show. While dating her, he regularly cheats and lies to both her and Tony. What makes us genuinely despise Jackie is his treatment of Meadow Soprano ( Jamie-Lynn Sigler). Jackie is a lazy wannabe who flunks out of school to become a lackey to Ralph Cifaretto ( Joe Pantoliano). RELATED: Worst Lead Male Characters in Modern Cinema Even before he starts doing criminal acts, his demeanor, smirk, and body language is enough to make watchers loathe him. Instead of using his immense privilege to get an easy white-collar job, Jackie squanders everything. The son of the deceased acting boss, Jackie Aprile, Jackie Jr. No other Sopranos character is more deserving of a firm slap to the face than Jackie Jr.
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