Kicking off our list is perhaps the show’s most off-kilter episode. Coming towards the end of the fifth season, The Test Dream may not have had the full-throttle spills, thrills and kills that other episodes did, yet it remains one of the show’s most memorable offerings. It begins with Tony checking in at the Plaza Hotel, where he enjoys some lavish room service and the services of a prostitute - a rather quiet evening in by his standards. He falls asleep, and we are taken on a surreal journey into the big man’s psyche through a twenty minute dream sequence.
The show had given us a window into Tony’s dreams before (as we will see later in this article), but never to this depth. It’s fair to say Tony had a lot on his plate at this point of the series - there was the breakdown of his marriage to Carmela, ongoing tensions with the New York family, and his erratic cousin Tony Blundetto becoming an ever-growing liability. These anxieties filter into his dream - at one point his teeth fall out, which according to the dream dictionary, symbolises a loss of power. The audience is used to watching Tony vocalise his problems in Dr Melfi’s office - here we are seeing how he deals with them internally, and it makes for compelling viewing.
The Test Dream perhaps comes closer than any other film or TV series in depicting the messy absurdity of dreams. The cinematography is suitably quirky, with characters talking directly to the camera and a memorable visual when, after Tony is being nagged by Carmela to get dressed, he points to a television that is showing him doing just that. Likewise the cameo of Annette Bening (complete with Tony’s goofy reaction) perfectly captures the randomness of dreams. In a lesser show this type of storytelling would feel like a gimmick - not here. Indeed, Tony’s dream foreshadows at least a couple of key events that would affect the direction The Sopranos would go (more on that later). The Test Dream is a unique achievement that lingers long in the memory.