7. Jon Favreau - The Sopranos
Jon Favreau's appearance in The Sopranos was one of the more unexpected moments in a show that was hardly predictable. With a subplot that took place on a film set in New York, this was a more lighthearted, meta episode, poking fun at Hollywood’s unhealthy romanticisation of gangsters, all whilst... romanticising gangsters.
Favreau is directing a film starring Janeane Garofalo and Sandra Bernhard when he meets young gangster Christopher, who harbours a secret desire to work in the film industry. Favreau becomes intrigued by the hardened criminal and tries to coax street stories out of him - but Christopher turns out to be too much for the sheltered director.
The subtext of the episode is Hollywood's uneasy relationship with crime. Many filmmakers have an unhealthy obsession with the lawless underworld, even though their effete lives never overlap with those of their subjects.