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Over its eight-year run, The Sopranos (1999-2007) proved it could pull from the film world with the best of TV shows. It went beyond the guest-star turn by Burt Young (Chinatown, Rocky) and the recurring role played by actor-director Peter Bogdanovich. At one point, Mike Nichols was set to play a psychiatrist on season 3 of The Sopranos.

Quentin Tarantino was another film director Sopranos producers had in mind for the landmark HBO series. If everything had worked out, Tarantino would have played an exaggerated version of himself. In the end, Jon Favreau played the role in what became a standout episode of season 2.

A ‘Sopranos’ writer wrote the ‘D-Girl’ director part for Quentin Tarantino

Quentin Tarantino points at the camera at a film premiere
Quentin Tarantino during “The Green Mile” -benefit premiere at Mann Village Theatre | SGranitz/WireImage

After getting his start as a TV writer on The Visitor and Providence, Todd Kessler earned a shot in the Sopranos writers room during the show’s second season. On the Talking Sopranos podcast, Kessler recalled getting the assignment for “D-Girl” (season 2 episode 7) as a test episode.

“David [Chase] gave Terry [Winter] and I episodes to write as kind of trial episodes,” Kessler said. “So ‘D-Girl’ was a trial episode.” In that ’00 installment, Christopher (Michael Imperioli) really catches the Hollywood bug. This time around, he believes he can get his script to a working film director.

That because Christopher’s cousin (just in town from California) is dating a film studio executive (played by Alicia Witt). During the course of their visit, Christopher goes on a film set to see a scene being shot by the director, played by Jon Favreau. Had Kessler gotten his first choice, Tarantino would have played that part.

“Initially, I wrote it for Quentin Tarantino,” Kessler said on Talking Sopranos. “I did a lot of research into Quentin Tarantino[‘s personality] for it. His personality is more known now that it was at that time [circa 2000].” But Tarantino couldn’t play the role for some reason.

‘Sopranos’ writer Todd Kessler loved that Jon Favreau got the role

Vince Vaughn, Drea De Matteo, Jennifer Esposito, and Jon Favreau seated together at a club, circa 2000
Vince Vaughn, Drea De Matteo, Jennifer Esposito, and Jon Favreau at the reception for a Carl Thomas album release| Steve Azzara/Corbis via Getty Images
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Looking back, Kessler couldn’t recall why Tarantino didn’t play the director in “D-Girl.” “It turned out, either he wasn’t available or supposedly he didn’t get it,” Kessler said on Talking Sopranos. “When Jon [Favreau] came as a possibility, I loved that idea.”

The part required the actor to send himself up a bit (as Ben Kingsley later did on The Sopranos). Clearly, Favreau had no trouble doing that for his “D-Girl” role. “He has such a great sense of humor and playfulness,” Kessler said. “He was totally game for somewhat lampooning himself.”

Favreau, then gearing up to direct his first feature film (2001’s Made), didn’t waste his time on the set. According to Vincent Pastore (Sal “Big Pussy” Bonpensiero), Favreau hired him to play a mobster in Made during the “D-Girl” shoot.

Pastore wasn’t the only actor who turned up in Favreau’s film. Drea de Matteo (Adriana la Cerva) also appeared in Made as a club girl who parties with the main characters.

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