The Sopranos: The 5 Funniest Episodes (& The 5 Most Disturbing)
The Sopranos had a way of mixing disturbing violence and dark thematic material with laugh-out-loud humor, creating all kinds of enjoyable episodes.
Over the course of its six seasons, The Sopranos changed television in a number of ways. It was the first cinematic hour-long drama series of its kind. It was the first television show in which the main “hero” character is at best an antihero, at worst an outright villain.
It was also among the first shows to mix disturbing violence and dark thematic material with laugh-out-loud humor, making it an exciting and unpredictable viewing experience each and every week. Some episodes were funnier than others, and some episodes were truly disturbing.
Funniest: “Pilot”
The pilot of The Sopranos differed from the rest of the series in many ways, not the least of which was its emphasis on comedy. There is a murder in the episode, but it’s not particularly graphic or emotionally powerful. Rather, the episode strikes a more humorous tone, sometimes using broad comedy, like when Carmela busts out a machine gun before investigating a mysterious sound, only to find Meadow climbing out her bedroom window.
Later in the episode, when Tony goes to confess to Carmela about seeing a therapist, she gives him a strange look. He asks, “What are you doing?” To which she replies, “Getting this wine ready to throw in your damn face.”
Most Disturbing: “Employee Of The Month”
One of the most disturbing scenes in Sopranos history is when Tony’s therapist, Dr. Melfi, is raped. The scene is long and unflinching in its realism, and would be upsetting to watch in any case, but is especially disturbing given that the audience feels attached to Melfi, a main character on the show.
Additionally, Tony faces a moral dilemma regarding how to deal with it. He wants to track down the assailant and exact mob justice, but he also weighs the more legitimate option, which is to let the law deal with him.
Funniest: “To Save Us All From Satan’s Power”
Season three contained two of the show’s funniest episodes, the first of which being “To Save Us All From Satan’s Power.” It’s a Christmas episode, and the guys are throwing their annual community Christmas party at their social club.
The problem is, their regular Santa Claus is Sal Bonpensiero, who they recently whacked. They force Bobby Bacala to take over, even though he’s too shy to do a good job. Paulie asks Sil, “Would it kill him to say ‘Ho, Ho, Ho’?”
Most Disturbing: “Soprano Home Movies”
The Sopranos undoubtedly got darker in tone with each season. One of the most disturbing episodes is season six’s “Soprano Home Movies,” in which Tony and Bobby get into a physical fight when Bobby lashes out over Tony’s persistent ribbing. Tony loses the fight, which hurts his ego as much as his body.
He retaliates by forcing Bobby to carry out a hit for the first time in Bobby’s life – he famously had never killed before. Bobby obliges and comes back a changed man. This episode showed Tony at his most evil and vindictive, taking what was left of Bobby’s innocence for purely spiteful reasons.
Funniest: “Pine Barrens”
“Pine Barrens” is widely considered one of the best episodes in Sopranos history. A simple collection trip goes haywire when Paulie’s attitude gets the better of him, and he and Christopher end up chasing “The Russian” through the snowy woods, where they get lost for the night.
The banter between the two characters is hilarious, as is a scene on the phone between Paulie and Tony, where Paulie misunderstands just about everything Tony says and relays his nonsensical translation to Christopher. The episode was directed by Steve Buscemi, who would later co-star in the acclaimed fifth season of the series.
Most Disturbing: “Long Term Parking”
When a character is “flipped” by the FBI, it’s almost always a sign that their days are numbered, as it’s only a matter of time before the wrong people find out about it. In season five’s “Long Term Parking,” Adriana, one of the show’s main characters, is killed by Silvio after admitting to Christopher that she’s been compromised.
Her death scene is harrowing, but even more emotionally disturbing is the scene where she admits to Christopher that she’s been gotten to by the feds. He beats her and strangles her, almost to death. He finally relents and collapses in tears. It’s perhaps the most emotionally raw scene in the entire series.
Funniest: “The Strong Silent Type”
The Sopranos often combined comedy with dark, mature themes, and “The Strong Silent Type” is a perfect example. The most memorable scene by far is the intervention that Adriana sets up for Christopher, where she, along with his mother and his colleagues, confront him about his drug use.
After Adriana’s heartfelt, pre-written speech, Silvio and Paulie take over, who are, to put it mildly, less eloquent in their remarks. The scene unfolds as one would expect given the characters involved, and the result is one of the funniest scenes in the entire series.
Most Disturbing: “Live Free Or Die”
“Live free or die,” the title of the episode, is an acknowledgment of how awful the main plotline is. This is the episode in which Phil Leotardo watches as his goons beat Vito Spatafore to death simply because he’s gay. They had been looking for him for a while, and Tony had been protecting him, not wanting to condemn one of his most loyal soldiers to death for such a reason.
Finally, Tony caves to Phil and gives him up. It’s an episode so dark and maliciously subversive that it likely would not have been approved by the network had the show been running in 2021.
Funniest: “Eloise”
Carmine Lupertazzi, Jr. was one of the funniest side characters on The Sopranos, appearing in 16 episodes between seasons four and six. He’s the heir to the New York family throne but doesn’t have the smarts for the job. Every scene with him is a linguistic adventure. He’s famous for his malapropisms like the ones in this episode, where he utters the classic line, “He’s an old fashioned guy, very allegorical.”
Just as funny as Carmine himself are the reaction shots of his associates whenever he commits a linguistic error or social faux pas. They can’t believe they have to humor him, but they do. His father’s the boss.
Most Disturbing: “University”
Season three’s “University” follows the plight of an innocent young stripper at the Bada Bing who’s dating Ralph Cifaretto, one of the show’s most vile characters. While high on cocaine, Ralph viciously beats her to death outside the club after she confronts him about his boorish and abusive behavior towards her.
The misogyny and shocking cruelty of this episode not only caused many viewers to stop watching the show, but many canceled their HBO subscriptions altogether in protest. Despite the controversy it generated, “University” was a fitting reminder that although The Sopranos can be a funny and entertaining series, its characters are, at the end of the day, ruthless and amoral killers.
