Through its six-season run, classic HBO drama The Sopranos featured several unexpected cameos from real life celebrities. These included: director Jon Favreau, actor Ben Kingsley, and most hilariously: New York Jets head coach Eric “Man-genius” Mangini (whose team was coming off an impressive season at the time of filming but will go 4-12 the following year , leading to Mangini’s eventual firing).
Of all the celebrity cameos on The Sopranos, however, none hit quite as hard as actress Annette Bening’s brief appearance in the season 5 episode “The Test Dream.” Bening, who is one of the most accomplished performers of her era (nominated for four Oscars for her work in The Grifters, American Beauty, Being Julia, and The Kids Are Alright), kindly stopped by to film a couple of scenes for the 20 -minute dream sequence that Tony Soprano (James Gandolfini) experiences for much of the episode’s runtime. It’s such a bold, out of left field casting decision that even nearly 20 years later it still stands out.
Bening talked about filming the episode with The Daily Beast in 2020, saying:
“I received the episode out of nowhere, and read it, and thought, ‘Wow—this is fantastic, and bizarre, and surreal.’ I spoke to [Sopranos showrunner] David Chase briefly, and went and shot it a day in New York. You’re just in the midst of trying to find these moments and figure them out, so it was really fun. I can see, even as we did it, that this was a world in which all of the actors who were there every day working on the series, it was very familiar to them. They had been working long days for years and years, so it’s a lot of hard work for them. But it was a lot of fun, and really a lark!”
What exactly makes Bening’s so strange and so effective? The answer ultimately comes down to how seemingly random it is. While The Sopranos was successful at quite any dramatic endeavor it set its mind to, it was particularly adept when it came to dream sequences. Sopranos creator and showrunner David Chase was inspired by David Lynch’s deployment of dreams in his hallmark series Twin Peaks and sought to capture similar feelings of unconscious dread with The Sopranos.
Viewers will receive privileged peeks into Tony Soprano’s dreams several times throughout the show but the Annette Bening-starring dream at the center of “The Test Dream” was by far the longest. As is often the case with Sopranos dream sequences, this one begins with something weighing heavily on Tony’s mind. As he checks in to a swanky Midtown hotel for a little break, Tony is dealing with the fact that his New York rival Phil Leotardo (Frank Vincent) has just murdered Angelo Garepe (Joe Santos) during a protracted power struggle. Tony knows that his cousin Tony Blundetto (Steve Buscemi) is thinking about hitting Phil back even though that would be beyond ruinous for him and maybe even the New Jersey crew at large.
Worried about his cousin, Tony falls asleep and … dreams about Annette Bening? Pretty much, yeah! Although Tony B does eventually make an appearance and assassinates Phil Leotardo with finger guns, Tony’s long “test dream” is really a mismatched mosaic of anxiety, insecurities, and pop culture fixations that he’s developed over his life. Because that’s what dreams are. They only feel vaguely linear when we recount them to someone the following morning. In the moment, however, there’s no dramatic throughline.
Indeed, Tony’s dream goes all over the place. It begins in said hotel room where he wakes up to find former New York mafia don Carmine Lupertazzi (Tony Lip) in his bed. Although Carmine is surprisingly one of the few mob-related figures that Tony hasn’t killed or ordered killed, he still feels acutely uncomfortable by the presence of the dead man in his room. Probably because he knows it’s the fate that will eventually await him.
From there, Tony’s dream pulls him off to his therapist Dr. Melfi’s office though it’s not Melfi who is administering psychotherapy but his (also dead) mistress Gloria Trillo (Annabella Sciorra). Then, after watching bits and pieces of his life on TV (and guest appearances from more corpses) he ends up back where he really wants to be: in his home with his estranged wife Carmela (Edie Falco). Tony’s brain knows he wants to get back together with Carm but first they have an important chore to do: meet their daughter Meadow’s boyfriend Finn’s parents. And that’s where Annette Bening comes in.
