Annette Bening on The Sopranos Remains the Strangest Cameo in TV History

The Sopranos always made the best of its dream sequences and legendary actress Annette Bening was happy to help out.

Annette Bening in The Sopranos
Photo: HBO

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.

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 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!”


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