3. Annette Bening
Episode: Season Five: The Test Dream Keeping with the Oscar nominees, this four-time Academy Award nominee is the sole entry on this list that is playing herself - albeit in a dream. Bening appears in The Test Dream in Season 5. This episode is where Tony spends a night in the Plaza in New York and sleeps uneasy worrying about his livewire cousin Tony Blundetto (Steve Buscemi). Bening plays the (imagined) mother of Tonys future son in law, Finn who is recently engaged to Tonys daughter Meadow (Jamie-Lynn Sigler). Tonys imagination is always fervid and creative and even calls her out on her fame asking: Youre Annette Bening, aint you? Bening is no stranger to the gangster genre as she starred in Warren Beattys
Bugsy (to whom she later married). The episode is one of the most notoriously trippy as it is almost entirely set in Tonys subconscious. Bening is not the only Hollywood actor to play themselves on the show. Ben Kingsley and Lauren Bacall also appeared as snooty versions of themselves in the final season. Kingsley was courted for the antagonist role in Cleaver by Christopher and Little Carmine while Bacall was violently mugged by Christopher. Cleavers lead role eventually went to Daniel Baldwin who channelled his inner Tony Soprano for the part. http://www.youtube.com/watch?v=BHtq9iPaK2c