The characters of The Sopranos are endlessly enjoyable, but they also aren't always very smart. Part of the show's charm is in its ability to deftly show a balance of characters that both commit horrible acts yet somehow still remain likable, making them both richly complex and endlessly fascinating to watch.
The show also walks a fine line between drama and comedy, and much of the show's humor derives from the stupidity of the characters. They certainly aren't the smartest mobsters, often spouting hilarious misquotes and dreaming up terrible ideas that backfire in often unforeseen and tragic ways. These plans certainly weren't thought through.
When Adriana Tells Christopher About The FBI
This isn't the worst plan per se, but Adriana was wickedly naïve in believing that Christopher would take her snitching in stride. Adriana had good intentions in telling Christopher that she was working with the FBI - it relieved her guilty conscience, and she hoped that Chris would run away with her and enter witness protection.
Unfortunately, the plan completely backfired, and in the worst way possible. Chris betrayed Adriana by going to Tony, and Tony had Silvio whack Adriana in the woods.
When Sean And Matt Attempt To Whack Christopher
Christopher was at the center of many notable episodes, including season two's "From Where to Eternity." In the preceding episode, Christopher had been shot and nearly killed by Sean Gismonte and Matt Bevilaqua.
Both Sean and Matt were feeling underappreciated in the mafia and had the horrible idea to kill Christopher for Richie, hoping that the assassination would earn them some respect and recognition. Instead, Sean was killed by Christopher on-site, and Matt was later taken to a warehouse by Tony and Big Pussy and killed.
When Big Pussy Works With The FBI
Working with the FBI from inside the mafia is never a good idea. In this case, the show did exactly what fans thought it would do. Big Pussy had been working with the FBI after getting busted on a heroin deal, and he took to his newfound role with incredible enthusiasm.
However, Tony eventually deduces that Big Pussy had flipped and takes him out on a boat. It's there that he, Silvio, and Paulie kill him and dump his body in the ocean, and it's just one of many FBI-related deaths to occur in the show.
When Mustang Sally Beats Up A Connected Guy
One of the dumbest characters in Sopranos history is found in the third season episode, "Another Toothpick." At the beginning of the episode, Mustang Sally had the horrible idea to whack Bryan Spatafore over the head with a golf club for interfering between him and his girlfriend, Tina Francesco.
Bryan is a connected man, as his brother is made man, Vito Spatafore. In retaliation for the attack, Mustang Sally is killed by the sick and ailing Bobby Bacala Sr., who also happens to be his godfather.
When Artie Tries Investing
Artie was never the smartest person in the show, but the fourth season episode, "Everybody Hurts," shows him at his worst. Artie takes a liking to a new French waitress at his restaurant, and her brother looks to distribute a special French brandy in America. To do so, he needs $50,000 for the distribution rights.
Artie agrees to spot the man in exchange for 13 percent interest, and he eventually gets the money from Tony. Of course, then everything goes horribly wrong - the deal falls through and Artie loses the money, gets beaten up, and nearly takes his own life, fearing Tony's wrath.
When Tony B Stops Going Straight
Tony Blundetto emerges from prison and makes a valiant effort to go straight. He shows an impressive amount of initiative in regards to his career as a massage therapist, and he actually comes within days of opening up his own business when he snaps under the pressure of civilian life.
He beats up the storefront owner and runs back to Tony, asking to rejoin the family business. It's a horrible plan, and it ends in a predictable fashion with one of Tony's coldest kills of the series.
When Davey Joins Tony's Poker Game
The Sopranos had a penchant for throwing civilians into Tony's inner circle and watching the chaos play out. Perhaps the worst offender is Davey Scatino. Davey suffers from financial troubles and decides to join Tony's poker game against vehement protest from Tony himself.
But either through bad luck or poor skill, Davey loses even more money playing poker and falls even deeper into debt with the mafia. In return, Davey's sporting goods store is eventually busted out by the mob, and Davey is left feeling desperate and suicidal, eventually relocating to Nevada.
When Jackie Jr. Tries Robbing Eugene
Few characters are as tragic (or as stupid) as Jackie Jr. Jackie showed promise in college, but he eventually succumbed to the lure of mafia life and fell deeper and deeper into its grip.
Influenced by Ralphie's story about Tony and Jackie's father robbing a card game, Jackie Jr. decides to follow in his father's footsteps and robs Eugene's card game. Unlike Tony's attempt years before, this one goes horribly wrong, and Jackie ends up on the lam. He's eventually tracked down and whacked by Vito Spatafore.
When Paulie Goes Against The Family
Paulie was one of the surviving Sopranos characters to make it to the finale, but only because of the good graces of Tony Soprano. Paulie went behind the DiMeo family's back on multiple occasions, feeding juicy information to Johnny Sack and the New York outfit. Naturally, this gets him into some deep trouble with the DiMeos - especially when it came to telling Johnny about Ralph's inappropriate joke against Ginny.
Tony seems to know that it was Paulie who ratted on Ralphie and nearly kills him while in Miami. And while Tony gets within seconds of whacking his old friend, he eventually decides against it.
When Tony Buys Whitecaps
In the magnificent fourth-season finale, Tony purchases a beachfront property on the Jersey Shore as a last-ditch, desperate attempt to save his crumbling marriage. As Carmela correctly surmises, it's "just a bigger version of an emerald ring so [Tony] can go on with [his] other life."
And while the plan initially seems to work, everything comes crumbling down once a jealous Irina informs Carmela of Tony's affair with Svetlana. Tony not only loses his marriage but he gets stuck in a confrontational back-and-forth with the house's owner regarding his lost deposit.