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 would 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.
“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 in 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 could 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 pretty much 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 would 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! Though 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. Though Carmine is surprisingly one of the few mob-related figures that Tony hasn’t killed or ordered killed, he still feels profoundly 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 drags 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 importance chore to do: meet their daughter Meadow’s boyfriend Finn’s parents. And that’s where Annette Bening comes in.
While we never meet Finn’s actual parents in the show, in Tony’s dreamscape they are corrupt (and dead) New Jersey detective Vin Makazian (John Heard) and actress Annette Bening. And we mean literally actress Annette Bening. Tony asks her if she’s Annette Bening and she nods affirmatively before getting annoyed with his pestering.
Annette Bening is in Tony’s dream because Annette Bening is probably in a lot of dreams of cinephiles in their mid-40s. But also: even amidst all the intensely personal imagery and concepts in Tony’s dreams, The Sopranos is indicating that the larger cultural landscape is inescapable. Before Tony meets Bening, he sees his favorite actor Gary Cooper on a TV in Nuovo Vesuvio. And when he and Vin Makazian leave the table to go pee (something that Tony mournfully observes the dead Vin can’t do anymore), the dream Bening blurts out a line from The Godfather: “I don’t want my husband coming out of there with just his cock in his hand.”
Bening’s dream cameo even extends into the next phase of the dream where Tony finally confronts his anxiety over how his cousin will respond to Angelo’s murder. As Tony witnesses Tony B kill Phil in the streets, a crowd of onlookers gather to chastise him for not stopping it. Among the onlookers is Annette Bening, whose raised hand de facto dream M.C. Gloria Trillo acknowledges with a hilarious “Annette Bening?” Annette simply wants to say “There’s something bugsy about him,” which is referring to Tony and also the 1991 film Bugsy she starred in alongside her real life husband Warren Beatty about gangster Bugsy Siegel.
If this is all starting to sound weird and exhausting that’s kind of the point. Dreams only make the slightest bit of sense when you glance at the highlights. For Tony, that clearly points to the stress he’s experiencing over Tony B. But the path that his dream takes to get there is a circuitous one. And not only that, but it doesn’t even stop with the murder of Phil Leotardo and Annette Bening’s probing questions of it.
After the Leotardo murder in dream world, Tony’s mind throws him right back to high school where he encounters his true nemesis: his high school football coach. As Coach Molinaro chastises Tony over his lack of ambition, Tony attempts to execute him but he drops his clip and all the bullets therein turn to ash in his hand. This is the “test” portion of “The Test Dream” title – the one where you’re assigned an important task (a test in high school) and your brain gleefully orchestrates your failure of it.
Hilariously, the Coach Molinaro portion of the dream might be the only part of it Tony actually remembers. Usually, people only recall the snippet of a dream they were experiencing right before waking and later on Tony calls Carmela to tell her he had the “Coach Molinaro” dream again.
That doesn’t mean, however, that the Annette Bening of it all was all for naught. She was an important part of Tony’s dream journey. What part exactly? Well, she was there. And when it comes to dream logic, sometimes that’s the best you can do.