1. Pine Barrens (season 3)
Written by Terrance Winter (later creator of Boardwalk Empire) and directed by season 5 cast member Steve Buscemi, this is hands down my favorite episode of the series. Christopher and Paulie have to pick up money owed to an ill Silvio, and they get into an argument with the guy, Valery, and end up killing him, so they think. So they drive to South Jersey to bury the body in the woods.
When they get there, it turns out he is alive and so they make him dig his own grave. Before he finishes though, he hits Chris with the shovel and takes off. Paulie or Chris clip him in the head with a bullet but he keeps running and they lose him. It turns out that they are lost as well and have to spend the night in the cold. There are some great exchanges between the two as they try to stay warm in an abandoned van. It also includes one of my all-time favorite moments, which is the messed up exchange about whether or not Valery was an interior designed. And of course the lore for this episode has grown as “what happened to the Russian” has turned into the second most wondered about question on The Sopranos.
2. College (season 1)
Heralded by many (including Time magazine) as the best of the series, and according to TV Guide the second best episode of television ever. Allen Coulter directed this one (and a couple of others on this list) that has Tony flying solo (Carmela is sick) on college visits with Meadow. She asked him questions about being in the Mafia, and it might be the first chance in the series to really see Tony’s worlds overlapping. Tony tracking down the former snitch, and Carmela’s weird night with Father Phil add to a solid episode.
This episode won an Emmy for best writing, and was Edie Falcos submission that year for Lead Actress.
3. Whitecaps (season 4)
Another repeat director on this list, John Patterson, handled this one that is widely considered to be another of the shows best. The whole storyline with the beach house, and how things seen to take a 180 from the beginning to the end of the episode. Tony and Johnny Sack plot to take out Carmine Lupertazzi, before Tony bails at the last minute. Junior’s jury is deadlocked after he is intimidated by members of the Soprano family.
But it’s the argument between Tony and Carmela that gets the most press in this one, and rightfully so. It’s a very powerful exchange, and worthy of the award recognition. It’s probably one of the three or four best scenes in this episode.
James Gandolfini and Edie Falco both won Emmy’s based on this episode. It also won the Emmy for writing.
4. Funhouse (season 2)
The season two finale, also directed by John Patterson, is a big one. Tony gets food poisoning, which leads to a bunch of dream sequences, which are generally my least favorite part of this show, but fit really well here. Tony eventually uses his hallucinations to further investigate “Big Pussy” possibly being an FBI informant. He, of course, finds it to be true and eventually he, Silvio and Paulie take him out and throw his body in the ocean.
It was nominated for a writing Emmy.
5. Long Term Parking (season 5)
Terence Winter is back, with Tim Van Patten (another Boardwalk Empire guy) directing. This is a big episode for a couple of reasons. It was part of the excellent 5th season, and featured a key point in the Tony Blundetto storyline, as he finally resurfaces and calls Tony. Adriana get’s arrested for her involvement in the club murder and eventually confesses to Chris that she has been talking to the FBI. The scene that follows, with her getting killed remains one of the most shocking episodes of TV. It was so gruesome that the act isn’t even shown on TV1.
Won Emmy for writing and support actress (Drea de Matteo) and got nominated for directing.
6. Kennedy and Heidi (season 6)
Future Mad Men show runner Matthew Weiner penned this one, the fourth to last episode in the series. It really represented the beginning of the end, and featured one of the shows most shocking moments, Tony finishing off Christopher after the car crash. Tony had issues with Christopher all along, and at one point thought he was the future, before drugs derailed him. After Christopher confessed he wouldn’t pass a drug test, Tony did what he thought was best for Chris’ newborn child.
The Vegas scenes that followed show Tony taking drugs and having some sort of epiphany that indicates that Christopher was the hex on his life all along.
It was an Emmy for directing, and was nominated for writing.
7. Made in America (season 6)
The series finale was one of the most anticipated episodes of television ever, and of course is remembered only for the cryptic last scene. The way that Agent Harris ultimately helps Tony get Phil Leotardo, the fact that Tony is likely to be indicted (if he lived), the peace between New York and Jersey, and the final visit to Uncle Junior all combine for a spectacular episode.
And the more I have watched the ending, the more satisfied I am with it, whether Tony died or not. I do, however, think that he did.
Also won an Emmy for writing.
- The Sopranos (S1) – The pilot.
- D-Girl (S2) – Jon Favreau’s cameo, and Chris’ first real attempt to crack the film industry.
- Another Toothpick (S3) – Another Terence Winter. Bobby’s dad makes a brief appearance.
- …To Save Us All from Satan’s Power (S3) – A bunch of Christmas flashbacks
- Whoever Did This (S4) – Tony kills Ralph.
- Irregular Around the Margins (S5) – The episode involves the made up affair of Tony and Adriana and won Michael Imperioli an Emmy.
- Marco Polo (S5) – Hugh’s birthday party that ends with a moment between Tony and Carmela
- Cold Cuts (S5) – The two Tonys and Christopher visit Uncle Pat’s farm to clean up some old business.
- Live Free or Die (S6) – Vito is officially outed.
- Which actually caused it to lead to speculation that she wasn’t actually dead [↩]