Celebrities Who Appeared As Themselves On The Sopranos

Early in 2020, Michael Imperioli and Steve Schirripa premiered the Talking Sopranos podcast. Imperioli had played the impulsive young mobster Christopher Moltisanti on the gangster drama The Sopranos while Schirripa played the dull-witted but big hearted Bobby "Bacala." With each installment of their podcast, Imperioli and Schirripa review The Sopranos one episode at a time, often interviewing fellow cast members and crew. The pair almost always ask their former co-workers if — during the making of the pilot episode — their guests could tell The Sopranos would become a cultural phenomenon. Some say yes, most say no, but whether they knew it or not, we know today The Sopranos has become one of the most well-remembered television series of all time.

As early as the second season, the show's success was clear among celebrity circles. In the beginning, the cast was made up of relative unknowns with the exception of Oscar nominee Lorraine Bracco, known for her role in Martin Scorsese's 1990 gangster epic Goodfellas. But by season 2 not only were other celebrities dying to get on the show, but a surprising number of them agreed to appear on the series as themselves. Some are wordless cameos while others are surprisingly involved. For a sampling of both, keep reading to find out the celebrities who appeared on The Sopranos as themselves. 

A quick warning for any Sopranos newbs — the following article contains multiple SPOILERS. We consider you warned.

Some of the celebrities who play themselves on The Sopranos show up in episodes focusing on Christopher's Hollywood pursuits. For the entire series he continues to circle back around to his dream of leaving the gangster life behind to make the same kinds of movies he grew up watching. An early example of this is season 2's "D-Girl" when a meeting with Christopher's cousin's fiancee Amy (Alicia Witt) gives him a front row seat to how movies are made. 

Christopher not only gets to meet celebrities in "D-Girl," he helps two of them with their jobs. As Amy escorts Christopher behind the scenes of a film in progress, Sandra Bernhard and Janeane Garofalo are filming their death scene. The pair are playing lovers and competing spies about to breathe their last, when Garofalo interrupts filming to complain about an insult her lover hurls at her that she "doesn't find particularly interesting." After the cast and crew — some of them more annoyed at the interruption than others — discuss options, it's Christopher who offers the solution. He gives them an Italian insult he assures the crew anyone in Brooklyn would know, allowing things to keep rolling and boosting his ego.

Garofalo shows up again later in the episode, when Christopher's star has fallen and he's no longer allowed on set. While he's not interested in helping her with dialogue, a few angry curses give her hints regardless.

By the time he appeared on The Sopranos, Montel Williams' popularity as host of the often controversial The Montel Williams Show had already peaked and dipped. It was still on the air, however, and it was no doubt his familiarity with navigating controversial topics that got him tapped to appear in the season 4 episode "Christopher."

One of the episode's subplots deals with the still contentious subject of Christopher Columbus Day. As the holiday approaches, media spreads about planned protests from Native American organizations, a subject that Soprano family consigliere Silvio Dante (Steven Van Zandt) takes personally. Even though no financial stakes are involved — and Tony (James Gandolfini) couldn't care less — Silvio recruits other gangsters to disrupt protests and lean on the organizers. 

Williams shows up on the Sopranos' kitchen television screen while Furio (Federico Castelluccio) and Carmela (Edie Falco) share coffee and wait for Tony to come downstairs. He mediates a debate between Native American activist Dr. Del Redclay (Larry Sellers) and the president of "a coalition of Italian anti-defamation organizations," Phillip Di Notti (Joseph R. Sicari). Through most of the clip, Montel seems firmly on Di Notti's side until the latter makes the mistake of calling his ancestors' journey to America the "middle passage," which was in fact the term used for the journey slaves were forced to endure on their way to the New World.

Halfway through season 2, Tony seizes control of the Executive game — a long-running, high-stakes poker game during which mobsters rub elbows with rich doctors, celebrities, and more. There's almost always a celebrity appearing as themselves in Executive Game scenes, and that includes season 5's "All Happy Families," after Tony puts the recently paroled Feech La Manna (Robert Loggia) in charge of the infamous card game. Singer David Lee Roth gets a seat next to the boss himself, along with a few lines of dialogue.

Roth doesn't have a lot to do in the scene besides play poker, though during a series of jokes about accountants and taxes, he offers the one-liner, "I used to be able to write off condoms." It would still be a few years before Roth made his long-awaited return as frontman for Van Halen, so unfortunately the rest of the band doesn't get to join him at the table.

Sopranos celebrity guests appearing as themselves don't usually have that much to do with the plot, but Jon Favreau's appearance in "D-Girl" is an interesting exception. Looking to develop a new project based on the real life mobster "Crazy Joe" Gallo, Favreau all too briefly invites Christopher Moltisanti into his circle so the young gangster can help him bring a more genuine feel to the film. 

Things don't end well between the two. They share a tense scene in Favreau's hotel room, where a coked-up Christopher "playfully" puts Favreau in a headlock and waves his gun around. Moltisanti is infuriated when he later skims a script and discovers Favreau has used an anecdote he shared with him in his Joe Gallo story. Favreau ducks Christopher after their hotel meeting, flying back to Los Angeles before the mobster can confront him. Even up until the latter parts of the series, Christopher still occasionally references his experience with Favreau souring him on the entertainment world.

In a 2014 Reddit AMA, Favreau said things between him and Christopher would've been a little different without his input. Asked about his appearance on the show, Favreau wrote that he spoke to Sopranos creator David Chase before filming the episode because the first script he received had him acting like "one of the guys." Favreau objected to that "because if the real Jon Favreau met the real Sopranos, he would not be very comfortable at all."

Sadly, Frank Sinatra passed away four years before he could even have the opportunity for a shot at a guest appearance on The Sopranos, but his progeny did their best to make up for his absence. In season 2's "The Happy Wanderer," we get our first glimpse of the Executive Game, including Sinatra's son, Frank Sinatra, Jr. If Frank Sinatra, Jr. is as stalwart a poker player in real life as he is in The Sopranos, then he's someone you probably don't want to be playing with unless you're a serious card shark. He's there when the game starts at night and is still playing the following morning. 

His passion for cards is finally overruled by his sense of self-preservation. When the always intimidating Richie Aprile (David Proval) shows up and starts pounding on Tony's old school buddy Dave (Robert Patrick), Sinatra wisely decides it's time to go. 

Apparently while having Sinatra as your last name gives you a comfortable status around wise guys, it doesn't make you immune to insults. After Sinatra pokes fun at Paulie "Walnuts" (Tony Sirico) for being mean to a younger gangster, Paulie warns the "Chairboy of the Board" to mind his business.  

He helps solves crimes on NCIS, is deported on The Ranch, and From Dusk Till Dawn: The Series, he's a centuries-old vampire. But to most, Wilmer Valderrama is doubtlessly best known as the love-starved foreign exchange student Fez on the popular sitcom That '70s Show. Valderrama makes a cameo in "Luxury Lounge," an episode that finds Christopher and Little Carmine (Ray Abruzzo) hoping to recruit Sir Ben Kingsley to their horror film Cleaver.

While Kingsley would clearly prefer if they were anywhere else, Christopher and Little Carmine follow him into the hotel's Luxury Lounge, where celebrities like Kingsley are offered expensive products for free. As the mobsters look around the lounge, overwhelmed by what they're seeing, Valderrama poses for a photographer. We don't see him again. 

While the former That '70s Show star doesn't get any dialogue, his presence does add an integral layer to the scene — highlighting just how alien this world is not only to the gangsters, but to the audience. You'd think they could've at least let Valderrama get in a "Good day, sir," but maybe that'd be too on the nose. 

In 2013's Iron Man 3, Sir Ben Kingsley made audiences laugh as Trevor Slattery, a drug-addled actor recruited to play at being a terrorist, but that wasn't the first time a Kingsley performance poked fun at his own profession. In the 2006 Sopranos episode "Luxury Lounge," Kingsley is stuck taking a meeting with Christopher Moltisanti and Little Carmine, who want him to play a mob boss in their upcoming film Cleaver. 

When we first see Kingsley, he's on his phone with his agent demanding to know why he's even meeting the gangsters, and starts cursing when he learns what we already know — that his agent set up the meeting to satisfy a gambling debt. During the gathering, it's obvious Kingsley isn't at all interested in what they're selling. When another celebrity walks by, he takes the opportunity to interrupt things by saying hello, and soon after cuts the meeting short. 

Kingsley is clearly playing a parody of himself and it's hilarious. When he bumps into Christopher on the elevator later, it's as awkward as running into someone you remember from a bad date. When they wind up on the same plane back to the east coast, Kingsley's response is one word (we'll let you guess what) and it's delivered perfectly. 

Geraldo Rivera gets in just under the wire. The former talk show host plays himself in The Soprano's final season. 

"Stage 5" gives us some landmark moments in the saga of the Sopranos. Not only do we finally get to see a few scenes from Christopher's film Cleaver, but we also see the final days of Johnny "Sack" (Vincent Curatola) as he succumbs to cancer. While Sack is technically the boss of one of the New York mob families, he's arrested at the end of season 5 and spends most of the rest of his life behind bars. 

Rivera's appearance touches on Sack's impending death, as well was one of the final season's chief conflicts. Rivera and his guests — two professional mafia experts who seem barely able to tolerate one another — discuss the power vacuum left in the New York City mob with Sack in jail. The candidates to replace Johnny are discussed, including Phil Leotardo (Frank Vincent), who becomes the Sopranos' enemy for the rest of the series. 

Diamond Dave isn't the only celebrity to show up as his own sweet self in season 5's "All Happy Families." Former New York Giants player Lawrence Taylor is there as well, though not at the same time as the Van Halen singer. 

Thankfully for Tony Soprano's bottom line, football isn't the only game Taylor likes to play. Early in the episode he shows up at the first of the Executive Games run by Feech La Manna. He doesn't get a lot of dialogue beyond jokingly greeting Tony as "Your Highness." 

But he does get a couple of consolation prizes. First of all, he wins the hand being played when the scene begins. Second, when you look around the room and think about how many characters in the scene are either in jail, in comas, or dead by the end of the series, getting cheated out of a little dialogue seems like a fair enough trade.

By the beginning of the final season episode "Chasing It," Johnny Sack is dead. With the exception of Phil Leotardo and Little Carmine — the latter of whom makes it known he has no more interest in running things — all the candidates to succeed Johnny Sack have followed him to the grave. Phil becomes the official boss of his family, and a celebrity is invited to celebrate his ascension. Not wanting to be shown up by her brother, Nancy Sinatra marks Phil's rise to power by performing her 2004 single "Bossman" at a private party.

Sinatra's appearance is interesting for a couple of reasons. On one hand, it's the only example of a celebrity appearing as themselves on The Sopranos acting at all flirtatious toward a recurring character on the series. Her performance of "Bossman" comes off as seductive, and later, when Tony and Phil take too long speaking to each other, she complains, "You two goin' home together?"

That could just be a throwaway joke, but there's probably another level of meaning. In the earlier episode "Cold Stones," when Phil has Vito Spatafore (Joseph R. Gannascoli) killed for being gay, Phil literally comes out of a closet before the kill, suggesting Phil's whacking Vito because of his own repressed sexuality. And it just so happens to be the consequences of Vito's death that Tony and Phil are discussing when Sinatra makes her wisecrack.

One of the hallmarks of The Sopranos are its wonderfully bizarre dream sequences which, in some cases, take over the majority of an episode and usually impart some important information to Tony. In the case of season 5's "The Test Dream," Tony's nightly visions revolve around the impulsive actions of his cousin Tony B. (Steve Buscemi), and they also give Oscar-nominated actor Annette Bening a chance to appear on the show as herself... or, at least, as a dream version of herself. 

She first appears as the mother of Meadow's (Jamie-Lynn Sigler) boyfriend Finn (Will Janowitz), and wife to Detective Makazian (John Heard), who dies in the first season. While Makazian awkwardly sings "Three Times a Lady," Tony taps her on the shoulder and says, "You're Annette Bening!" She smiles and nods. She isn't quite as polite the second time he taps her shoulder, and later in the dream her words signal catastrophe. While a crowd of bystanders is questioning Tony about why he didn't stop his cousin from killing Phil Leotardo, Bening raises her hand and says, "There's something Bugsy about him" — a reference to Bening's performance as real-life mobster Bugsy Siegel's lover Virginia Hill in 1991's Bugsy. Right after she says it, the crowd begins chasing Tony through the streets.

In "Luxury Lounge," actor Lauren Bacall helps save Sir Ben Kingsley from an awkward meeting with Christopher Moltisanti and Little Carmine, but it isn't the last time the acclaimed thespian meets Christopher. Later in the episode, in order to get out of yet another uncomfortable conversation, Kingsley tells Christopher and his friend Murmur (Lenny Venito) about the gift baskets given to awards presenters, some of which contain "$30,000 worth of merchandise." A few scenes later Christopher, in a ski mask, intercepts Bacall on her way to her limo after an awards ceremony and grabs her gift basket. When she resists, he knocks her to the ground with a punch.

While the scene plays like dark comedy, not everyone was laughing. In its Entertainment section, a New York Post writer railed, "How about breaking Kitty Carlisle's legs? Or taking Debbie Reynolds for a ride? And really, does Angela Lansbury still need her thumbs?" They went on to say the show had become "the biggest joke on TV" and argued that if Tony had died earlier in the season "it would have put us all out of our misery."

After hearing about Cleaver for so long, including seeing its writer — J.T. Dolan (Tim Daly) — beaten to a pulp in the middle of his own writing class, the film gets its premiere in "Stage 5." While Christopher and Little Carmine's overtures to Sir Ben Kingsley were doomed before they even began, Cleaver finds its stand-in for Tony Soprano in perhaps the least famous Baldwin brother, Daniel Baldwin. We see parts of scenes of Baldwin yelling at his underlings in his basement — in a robe and slippers identical to Tony's. We see him wooing the stand-in for the late Adriana (Drea de Matteo) and the film's titular zombie mobster getting revenge on him with his weaponized arm. Baldwin is there for the premiere's after party as well, shaking hands and taking pictures with Tony and gangsters. 

Baldwin is actually the only celebrity appearing as himself in The Sopranos who does so in more than one episode. After "Stage 5" he has a cameo in "Kennedy and Heidi" when he shows up to Christopher's wake to pay his respects.