Every person who ever appeared in The Sopranos considers it an honor, given the strong legacy of the HBO series. Among the show’s large cast were celebrities from various fields, and a couple of stars made cameos playing minor characters in single episodes, while some simply appeared as themselves.
Most of the celebrities who passed through were inserted into some of the best storylines in The Sopranos. While some were allies to the dangerous mobsters, others rubbed them the wrong way. Luckily, those that offended the mobsters got away with it, because it wouldn’t have made sense to whack a non-fictional and famous character.
Sir Ben Kingsley
Being a mobster wasn’t enough for Christopher. He wanted to be more. Eager to turn his moviemaking dreams into a reality, he pulled some strings and booked a meeting with British actor Ben Kingsley in Los Angeles. He was accompanied by Little Carmine, who intended to finance the movie.
Sadly for Christopher, Kingsley didn’t appear to be interested in working with him. He found an excuse to leave during their meeting. And when Christopher later asked him to get him an entry into a luxury lounge often frequented by the rich and famous, Kingsley refused to do so. Christopher followed him in anyway. Kingsley then officially turned down Christopher’s movie.
Aware of Christopher’s Hollywood dreams, Greg’s fiancée, Amy Safir—an assistant to Jon Favreau—invited him and Adriana to come on the set to see the director shooting his new film. Christopher was impressed and so he tried to convince Favreau to be the director in the movie he was planning to make. He even had an affair with Amy to make her push his idea to Favreau.
Christopher later spent some time with the popular director, showing him how fun the mob life was. He even let him play with his gun. Unfortunately for Christopher, Favreau left without accepting his proposal. Christopher then learned that Favreau had taken some of his ideas and used them to make a new movie.
David Lee Roth
Roth—the frontman of rock band Van Halen—attended one of Tony’s executive card games in season 5. In the card games, mobsters normally mingled with celebrities and top white-collar professionals who were addicted to gambling.
During the specific game, Tony tried to make a few lame jokes to see if his fellow mobsters would laugh. He had been earlier told that his juniors didn’t really find him funny. They only laughed at his joke because they feared him. It turned out to be true, as everyone laughed. Roth made a couple of better jokes too.
At the time of his appearance, Valderrama was one of TV’s most popular actors, playing foreign-exchange student Fez in the sitcom That ’70s Show. He could be seen in the background as Christopher and Little Carmine were busy begging Sir Ben Kingsley to work with them.
Christopher and Little Carmine followed Kingsley into the hotel’s luxury lounge, where celebrities were posing for photographs and being offered expensive products for free. Valderrama was then seen posing for a photographer, but he neither said a word nor interacted with any of the characters.
Frank Sinatra, Jr.
The late Sinatra Jr. also attended one of the executive card games. He was portrayed as an extremely skilled player, winning again and again, much to the dismay of other players. He didn’t get tired either, as he was still playing the following morning.
The game was ruined when the ever-violent capo Richie Aprile showed up and started beating up Tony’s old school buddy Dave. At that point, Sinatra decided it was time to go. Earlier, Sinatra had gotten into a disagreement with Paulie when he tried to tell him to treat a younger mobster respectfully. Paulie simply told him to mind his business.
After Lupertazzi Crime Family boss Johnny Sack died of cancer, former talk show host Geraldo Rivera was shown discussing the state of the New York mob with a few mafia experts. One of those experts named Manny Safie was actually played by popular scriptwriter Matt Weiner, who penned many of the show’s episodes.
While discussing the power vacuum with Rivera, the mafia experts predicted that Phil Leotardo will be the new boss. This turned out to be true, as Phil quickly assumed control and started a war with the DiMeo Crime Family.
Lauren Bacall is a Hollywood legend, and she appeared as herself in the hit TV show, passing by when Sir Ben Kingsley was having an awkward meeting with Christopher and Little Carmine. Kingsley began talking to her as an excuse to leave the meeting.
Later on, Bacall told Christopher how celebrities were normally given gift baskets containing more than $30,000 worth of merchandise. This was a wrong move, because Christopher decided to rob her. When Bacall was heading to her limo after attending an awards ceremony, Christopher intercepted her and grabbed her basket.
Emmy-winning actress Annette Bening appeared as herself in one of the show’s best dream sequences. In season 5’s “The Test Dream,” Tony Soprano dreamt about the impulsive actions of his cousin Tony Blundetto. Bening first appeared as the mother of Meadow’s boyfriend Finn and then as Detective Makazian’s wife.
While Makazian sang awkwardly, Tony recognized Bening, tapping her on the shoulder and exclaiming “You’re Annette Bening!” She simply smiled and nodded. And when Tony Blundetto killed Phil Leotardo in the dream, Bening remarked, “There’s something Bugsy about him” referring to Bening’s own portrayal of real-life mobster Bugsy Siegel’s girlfriend Virginia Hill in 1991’s Bugsy.
After getting turned down by a couple of Hollywood heavyweights, Daniel Baldwin agreed to star in Christopher’s movie and as a result, Cleaver was born. He gave an impressive performance, much to the joy of the mobsters.
At the movie’s premiere party, Baldwin could be seen shaking hands and taking pictures with the mobsters. It should also be noted that Baldwin was the only celebrity who appeared as themselves in more than a single episode. When Christopher died, Baldwin showed up at the wake to pay his respects.
When Phil Leotardo became the new don of the Lupertazzi Crime Family, a party was thrown for him. Nancy Sinatra was invited to perform and went on to sing her 2004 hit single Bossman, which was quite fitting.
Nancy came off as flirtatious and playful, and she absolutely killed the performance. Everyone was enthralled, and Phil was particularly taken with Nancy’s charm.