The Sopranos: Chasing It (2007)
Season 6, Episode 16
9/10
Chasing down a dark road
10 June 2023
Warning: Spoilers
Chasing It is sort of deceptively filler. It's gotten criticism for the Tony gambling arc, but this is something that did get set up in the previous season and we also saw more hints of in Remember When. If it had come completely out of nowhere I would understand that point more.

Tony succumbing to the dangerous highs of gambling is also interesting because not only did he beat the sh it out of an old friend back in season 2 who got addicted to gambling, but it makes him even more of a hypocrite to make fun of Christopher regularly over his soberism when he struggles with an addiction himself.

The fight between Tony and Carmela is fantastic! We haven't seen them lose their sh it over each other like this since Whitecaps (Which probably remains the most intense of the bunch), and the acting as well as dialogue deserves the highest amount of praise. The scariest part is that Tony doesn't have justifiable motivation for getting mad at her. He literally won the race, just not as much as he wanted to. Carmela was also right to be sceptical given how much more often he has lost at betting. So to see him flip out at her this badly over something that's 100% his own doing is absolutely bone-chilling and selfish, though Carm is the one who tries to hit him with an object from a distance.

Then we witness him losing one of his closest friends as he very begrudgingly pays back part of the debt very little at a time, going so far as to mock Hesh over his Jewish heritage.

Only once Hesh's wife dies out of the blue does Tony seem to feel remorse and pays him back the entire debt. But the damage is already done...

I enjoy the Vito Jr. Storyline too, which contains one of the all-time funniest lines from Phil ("You look like a Puerto Rican prostitute"). The kid is bratty, but there's a level of tragedy as well since he's simply lashing out over losing his dad as well as being humiliated by others that he was gay. The conclusion with him being forced off to boot camp is incredibly sad and disturbing.

Finally, A. J. tries to salvage the relationship with Blanca by proposing to her during dinner. She accepts it without really thinking it through. And what do you know, in the next scene between them she coldly gives him his clothes and returns the ring as well. That has to be one of the coldest break-ups I've ever seen onscreen. A. J. Might have been over his head hooking up with an older woman with two kids and even preparing for marriage, but that's no reason for her meanspirited and uncaring behavior towards him. This scene alone makes her one of the most unlikable characters in the series.

As an episode with nice understated tension and the compelling display of a delusional and self-destructive Tony, this is one that deserves a bit more credit than it gets.
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