The Sopranos

The Sopranos: 10 Most Cringeworthy Parts, According To Reddit

The Sopranos is a day in the life series about mobsters and in any real life scenario there will be some cringeworthy moments.

She-Hulk has upset some fans on Twitter recently due to a cold-open that had Wong spoiling major plot points of the legendary show. Some very important twists and deaths were rattled off in quick succession and viewers were not pleased. Fortunately, The Sopranos is such a rich and deep show that even spoilers won’t ruin the experience for first-time viewers

One can choose to watch just for the comedic naturalistic scenes that are dotted all over the show. The realistic nature of the characters and situations means that there are countless cringey scenes that can be difficult to watch with how well they hit close to home and how awkward the characters can act. Redditors have been happily pointing these scenes out for years.

Adriana’s Song, “Meow”

Season 1, Episode 10

Adriana dons an animal print coat at the opening of her new club in The Sopranos

Reddit user slidearea47 has one word for the most cringy moment in the show: “Meow.” This is a reference to the song Adriana shows Massive Genius for the band she manages. Early seasons of The Sopranos had Adriana making a run at being in the music business, but she could never quite get there.

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The only reason Massive Genius seems interested in hearing the sample tape is to spend time with Adriana, which is very apparent to Christopher who is in the room, as well. It’s hard to watch Adriana lip sync the “meow” lyrics of the song to the producer while the audience knows he has no interest in the actual music.

When Fran Felstein Sings To Tony

Season 5, Episode 7

fran felstein sopranos happy birthday

Anytime a TV show wants to replicate the historical moment of Marilyn Monroe singing “Happy Birthday” to President Kennedy, it’s always going to be cringe-inducing. Reddit user ErcoliS writes, “Haaaappy Biiiiirthday Mmmmmmr Pree-si-deeeent” as a reminder of how uncomfortable the moment is in The Sopranos.

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Tony has been hanging out with his father’s mistress and is having a great time hearing stories about her and his father’s life. But the more time he spends with her, the more he grows uncomfortable with the situation. And when she decides to sing him her rendition of “Happy Birthday,” it’s all Tony can do to not get up and leave the room.

When Carmela Tries To Talk About Billy Budd

Season 4, Episode 12

Carmela has dinner with her mom in The Sopranos.

Carmela Soprano often ends up being very cringy anytime she tries to relate to her kids and the many experiences they have had growing up. Redditor HollisFlaxseeds posts about one scene, “Carmela discussing Billy Budd and getting schooled by a bunch of college kids.” Carmela embarrasses herself in front of Meadow and her friends by trying to analyze Billy Bud.

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Most of the cringe comes because almost everyone has been in a situation where someone is trying to speak about a subject they are not too familiar with. Carmela has a naive and perhaps a bit homophobic understanding of the material and watching the college kids dismantle her argument is uncomfortable.

When Chris & John Favreau Hang Out

Season 2, Episode 7

Jon Favreau interrogates Christopher about the mob life

Chris’s Hollywood adjacent plot lines are always a little intentionally cringe-worthy. He’s a gangster who also sees himself as a screenwriter and the dichotomy between his violent nature and his attempts to write an interesting story are always funny. Redditor woolzie mentions one of these moments as cringy, “Chrissy rough housing with John favreau and how freaked out John got.”

The scene is uncomfortable both because it’s tense wondering how far Chris is going to go to mess with Jon and also because Jon is awkward as an in over his head director. During their conversation, director Jon Favreau talks to Chris like he’s a character, delighting in hearing the heinous things he’s done. When he’s confronted with the reality, things get uncomfortable quickly.

When Artie Bucco Tries To Shakedown The Investor

Season 4, Episode 6

Artie Bucco sopranos fight

Artie Bucco is a fascinating character in The Sopranos because he is as adjacent to the crime family as anyone can be while staying out of the business, for the most part. The few times that he does try to play the part of a gangster are so cringe-worthy because of how out of his element he appears.

Reddit user Half-Icy writes, “Qu’est-ce que c’est, man? Message machine broken?” This is a reference to the scene where Artie tries to scare the French investor who lost all of Artie’s money. Bucco’s tough walk-up and dorky, prepared gangster line, are completely undone when the smaller man rips out his earring and tosses him back outside.

When Tony Kisses Melfi

Season 1, Episode 6

Tony Soprano Dr Melfi Romance

Anytime Tony Soprano spends time with a female character on the show, it can be assured that he will eventually try to have a romantic relationship with her. It only takes six episodes for Tony to make a move on his therapist, Dr. Melfi in a very cringy scene as Redditor PowerOfDarkseid says, “Tony kissing melfi multiple times and getting rejected. That’s number 1.”

Tony isn’t used to being denied so when he approaches Melfi and tries to kiss her, her reaction is very embarrassing to watch. What makes it worse is that right after it’s over she continues talking like nothing happened but that she would like to continue exploring what just happened in their next meeting.

Nancy Sinatra Singing

Season 6, Episode 16

Nancy Sinatra sings her 2004 hit single Bossman at Phil Leotardo's party

The late series opening with Nancy Sinatra singing to the newly elected boss, Phil Leotardo, is still considered by many to be one of the lowest moments in the show. And some people, like one Redditor, can’t tell if it’s intentional or not, “I still can’t tell if the Nancy Sinatra/Phil scene is supposed to be ridiculous.”

There is a case to be made that this is supposed to be an example of how old-school Phil is, he still thinks being crooned to by an older singer is a “cool” idea. But Nancy’s acting is not particularly great, and the filming style makes the scene feel like an awkward music video.

The Freeze Frame And Swipe Transition

Season 5, Episode 10

Carmela sopranos freeze frame

The Sopranos is considered one of the best TV shows of all time, and anyone making a ranked list would be lambasted for not at least putting it in the top three. And while the acting and writing are widely hailed as game-changing, the filming and story-telling techniques are as impressive.

This is why one scene sticks out so badly. One Redditor, Repulsive-Data58, says, “The freeze frame/screen wipe when Carmela is walking away from Wegler. Yikes.” This scene is as awkward as it’s unexplainable. Carmela walks off and the screen freezes and then the scene transitions via a swipe to a completely different scene. It looks like something shot during a first week at film school.

When Artie Hits On Adriana

Season 3, Episode 5

Artie Bucco Adriana dinner date

Redditor LitAgent888 says, “…who doesn’t think the cringe king is when Artie rubs Adriana hand…” as their choice for most cringe moment in the series. Adriana La Cerva has been working at Nuovo Vesuvio under Artie Bucco, and like many characters in the show, he is taken with her beauty.

But she is currently dating Christopher Moltisanti and the feelings are not reciprocated. When Artie sits down with Adriana ostensibly to talk about business, it becomes clear that he means this to be a date. The awkward hand rubs and pitiful way that Adriana tries to avoid the situation without being rude are very tough to watch.

The Jackie Jr. Sit Down

Season 3, Episode 9

Jackie Aprile Jr. walking down the street before his execution in The Sopranos

Jackie Jr. is one of the tragic stories in The Sopranos universe. He’s mob-family royalty but is given the chance to do something legitimate with his life. However, the company he keeps and the pressure put on him by his family’s legacy nudges him into a life of crime, even though, in many ways, he is not up for it.

His attempts at acting like a gangster often end up looking ridiculous. Reddit user puremaddafty writes, “The “sit down” with Mattoush and Jackie Jr always makes me cringe.” Jackie Jr. acting like a gang boss for the younger generation just makes it all the more clear that he is playing mobster rather than actually being one.

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