As well as being a member of The Sopranos' DiMeo crime family Christopher Moltisanti (Michael Imperioli) was a budding Hollywood screenwriter, who relished any opportunity to rub shoulders with movie stars. Outside of Tony Soprano (James Gandolfini), Christopher had some of the best storylines in the whole of The Sopranos, from his struggles with addiction to his aspirations of becoming a Hollywood big shot. Interestingly, when Christopher finally realized his dreams, it signified the final nail in the coffin of his relationship with Tony.
In The Sopranos season 6, Christopher successfully got a feature film made, a Saw ripoff called Cleaver which was a thinly veiled admission of Christopher's guilt over the murder of his girlfriend and FBI informant Adriana La Cerva (Drea de Matteo). Cleaver also featured a repulsive mobster character, Salvatore, played by Daniel Baldwin, the violent revenge fantasy played out against Baldwin's character revealed to Tony the bitter resentment his nephew Christopher felt toward him. However, Daniel Baldwin wasn't the only Hollywood star that Christopher met during The Sopranos, and here's every actor, screenwriter, and director that he came into contact with in his journey to get Cleaver made.
6 Martin Scorsese
It's not the real Martin Scorsese that Christopher and Adriana see in The Sopranos season 1, episode 2, "46 Long". However, the Martin Scorsese Sopranos "cameo" sets up Christopher's filmmaking aspirations, and draws a direct line with one of the show's biggest influences. There are several Sopranos stars who have also appeared in Scorsese's gangster movies, such as Frank Vincent, who played Phil Leotardo in The Sopranos, and Billy "Bats" in Goodfellas. Brilliantly, Christopher doesn't mention any of Scorsese's gangster movies when he sees the filmmaker and instead voices his support for the director's Dalai Lama biopic Kundun, which was at the center of an international controversy when it was released two years earlier in 1997.
5 Jon Favreau
In The Sopranos season 2, episode 7, "D-Girl", Christopher gets to visit a real movie set, when his cousin's fiancée Amy (Alicia Witt) is keen to read his screenplay. Ultimately, Amy is like The Sopranos' Doctor "Cooze" Cusamano, thrilled by the connection to organized crime, but uncomfortable when confronted with the reality. As a result of Amy's attraction to Christopher, he gets to visit the set of Jon Favreau's new gangster movie, giving the director advice on the dialog. Favreau later appropriates one of Christopher's mob anecdotes in one of his screenplays, which infuriates him and sets up a recurring theme in Christopher's interactions with Hollywood stars.
4 Janeane Garofalo & Sandra Bernhardt
The stars of Jon Favreau's movie are Janeane Garofalo and Sandra Bernhardt, who are playing criminal lovers, and prompt Christopher's dialog feedback. In the scene that they're shooting, Garofalo objects to the use of the word "bitch", which prompts Christopher to suggest a Neapolitan word "pucchiacca" which has a harsher meaning and meets with Garofalo's approval. Garofalo later asked The Sopranos' Christopher for further dialogue advice when he visited the set, after falling out with Amy and Favreau, and takes his infuriated insults on board.
3 Sir Ben Kingsley
Sir Ben Kingsley is one of the first actors Christopher approached for the role of Salvatore in Cleaver. Having memorably played a mob boss in Jonathan Glazer's 2000 movie Sexy Beast, he was a good casting decision on the part of Chris. In The Sopranos season 6, episode 7, "Luxury Lounge", Christopher traveled to Los Angeles to cast his new movie with assistance from his key investor Little Carmine (Ray Abruzzo). As a British knight of the realm, it's hilarious to see Kingsley politely, but impatiently, sit through a meeting with the vulgar mobsters.
Despite Kingsley not being interested in Cleaver, Christopher, and Carmine continue to follow Kingsley around the luxury hotel. It's in these scenes that Christopher's Hollywood aspirations clash with his Sopranos gangster life. The amount of free items gifted to celebrities in the titular Luxury Lounge gives Christopher an idea, and he wants his own taste of the same luxury, something which is ultimately denied to him. However, Christopher gets another idea on how to profit from the luxury items given for free to Hollywood stars.
2 Lauren Bacall
Earlier in "Luxury Lounge", Ben Kingsley interrupted the meeting with Carmine and Christopher to say hello to Hollywood legend Lauren Bacall. Rather than a rude snub, Christopher and Carmine see it as another opportunity to bask in the glow of a Hollywood legend. Bacall is to be the host of an awards show in Los Angeles, and therefore stands to receive the luxury items that are dangled in front of The Sopranos characters. When Christopher confronts Kingsley about access to the Luxury Lounge, he discovers that awards hosts stand to receive $30,000 worth of free goods.
This $30,000 worth of goods is an impressive haul to take back to Tony and the guys back in New Jersey, so Christopher inevitably falls back on his gangster lifestyle. Waiting outside the venue, Christopher mugs Hollywood legend Lauren Bacall, punching her in the face and stealing her gift basket. When he offered some of the luxury goods to Tony, his boss was uninterested and was more concerned that Christopher's obsession with Hollywood had led to an avoidable situation involving credit card cloning at Vesuvio's. This Cleaver-centric clash shows how far the two characters have drifted apart, and foreshadows Tony killing Chris in The Sopranos season 6.
1 Daniel Baldwin
In The Sopranos season 6, episode 14, "Stage 5", Christopher finally premieres his movie, Cleaver. It's a lavish event that sees Tony Soprano brushing shoulders with Daniel Baldwin, who essentially portrayed him on-screen. One particular moment, in which Baldwin's character conducts a meeting in his basement, dressed in a white toweling robe and boxers is so clearly a reference to Tony, that it visibly upsets him. It's at this moment that Tony realizes that his relationship with Christopher is likely irreparable.
The production of Cleaver largely takes place during the gap between The Sopranos season 6, part 1 and part 2, so it's unclear how much Baldwin and Christopher interacted during production. However, the death of Adriana weighs heavily on the revenge plot of Cleaver, so it's likely Christopher was on hand to give Baldwin notes, as he was during the Favreau shoot. The two men clearly knew each other well enough as Daniel Baldwin was one of the guests at Christopher's funeral in The Sopranos season 6, episode 18, "Kennedy and Heidi". The final Hollywood star to meet Christopher was clearly his most successful interaction, but because of the film's thinly veiled digs at Tony Soprano, it also set up Christopher's tragic death at Tony's hands.