This article was originally part of the Insider Cinema guide to Hollywood, a website from the mid-2000s. We are reposting it here as both a writing sample and a guide for those seeking to get their foot in the door in Hollywood.

8½ (1963)  – Fresh off of the international success of La Dolce Vita, master director Federico Fellini moved into the realm of self-reflexive autobiography with what is widely believed to be his finest and most personal work. Marcello Mastroianni delivers a brilliant performance as Fellini’s alter ego Guido Anselmi, a film director overwhelmed by the large-scale production he has undertaken. He finds himself harangued by producers, his wife, and his mistress while he struggles to find the inspiration to finish his film. The stress plunges Guido into an interior world where fantasy and memory impinge on reality. Fellini jumbles narrative logic by freely cutting from flashbacks to dream sequences to the present until it becomes impossible to pry them apart, creating both a psychological portrait of Guido’s interior world and the surrealistic, circus-like exterior world that came to be known as “Felliniesque.” 8 1/2 won an Academy Award for Best Foreign-Language Film

The Cutting Edge: The Magic of Movie Editing (2004)  – The Cutting Edge: The Magic of Editing teaches the viewer how editors compile strips of film in order to create memorable moviegoing experiences. In addition to interviews with a variety of respected and award-winning editors, the movie offers clips form some of the most memorable films in the history of the art form.

An Evening with Kevin Smith (2002) (V)  – From the groundbreaking Clerks to the hyper-referential Jay and Silent Bob Strike Back, a lifelong comic-book fan, movie buff, and indie writer-director Kevin Smith is a filmmaker with a distinct vision. This film positions New Jersey native Smith before assembled groups of devoted fans from colleges all across the country, discussing his craft, his feelings, and his philosophy.

Get Shorty (1995) – A gangster is looking to get away from crooked deals and double-crossing people but ends up in the movie business anyway in this comic crime story. Chili Palmer (John Travolta) is a Miami-based loan collector for the mob trying to collect a gambling debt. His assignment takes him to Hollywood to collect money from Harry Zimm (Gene Hackman), a mildly sleazy producer of low-budget horror movies. Although Chili intends to hurt Harry if necessary, he takes a certain liking to him and an even keener interest in Karen (Rene Russo), Harry’s girlfriend, whom Chili recognizes from Harry’s grade-B monster epics. It seems Harry has a script that he feels is Academy Award material, and he could get the project off the ground if he could get the right actor for the lead — say, the well-respected but egocentric (and diminutive) Martin Weir (Danny DeVito). Chili thinks he has a feel for the movie business and decides to see what he can do to persuade Weir to get behind the project. Chili soon finds himself hip-deep in the film industry, which at least puts him in contact with a higher grade of scumbags than he’s used to. But Chili isn’t the only criminal Harry’s been dealing with; he’s been obtaining financing from Bo Catlett (Delroy Lindo), a drug dealer with a highly uncertain temperament. An intelligently constructed crime story and a hilarious look at the absurdities of the film business, Get Shorty was based on the novel of the same name by Elmore Leonard; Leonard based Chili on a real-life former gangster of his acquaintance, though Chili’s model never worked in Hollywood.

The Last Mogul: The Life and Times of Lew Wasserman (2005) – For the second half of the 20th century, Lew Wasserman was the most powerful man in show business, even if most people had no idea who he was. Born in Cleveland, OH, in 1913, Wasserman started out booking music for mob-controlled nightclubs, and soon became an agent for Music Corporation of America, which became the most lucrative music agency in America. As Wasserman rose through the ranks at MCA, he established such innovative business practices as “packaging” talent (booking hot acts only in tandem with other artists who were a harder sell) and took the company into managing acting talent in Hollywood, where he changed the film business forever by negotiating a ground-breaking deal for James Stewart on the film Winchester ’73, which reduced the actor’s up-front salary in favor of a cut of the movie’s profits, earning the actor a fortune in the process. Under Wasserman’s tenure at MCA, the company took over Universal Pictures, established the studio’s television branch (and made enough powerful friends make it the most important production outlet in the business), created the wildly successful Universal City studio tours, and expanded MCA’s recording branch into one of the biggest record companies in the world. Wasserman was also a man with no small degree of political influence (it didn’t hurt that Ronald Reagan was one of his early clients when MCA want Hollywood) and was reputed to have some useful connections to organized crime (his personal lawyer was reputed to be the model for Robert Duvall’s character in The Godfather). Wasserman was a secretive man who did not give interviews or commit anything to write if it could be avoided, but he knew nearly everyone of consequence in show business, and The Last Mogul: The Life and Times of Lew Wasserman is a documentary that through interviews with his friends and business associates paints a detailed portrait of his remarkable career, from his childhood in Ohio to his death in 2002.

New Suit (2002) – A guy looking for a break in the movie biz discovers the power of word of mouth in this satirical comedy. Kevin Taylor (Jordan Bridges) is an aspiring screenwriter who has pulled up stakes and moved to Los Angeles to pursue his dream. While working a day job, Kevin meets Marianne Roxbury (Marisa Coughlan), who is trying to work her way up the Hollywood ladder as a production executive. Biz-savvy Marianne advises Kevin that it makes more sense to spend his days schmoozing and making contacts rather than writing if he actually wants to get paid for his work and see it on a screen. With this in mind, Kevin takes a job as an assistant to Muster Hansau (Dan Hedaya), a once-powerful producer whose career is in a downward spiral. Kevin comes to realize he’s merely a glorified errand boy for a washed-up blowhard, and the only people he meets are fellow lackeys with little real pull in the business, so he decides to have some fun and starts talking up a screenplay called “The New Suit” by Jordan Strawberry, even though both the script and the writer exist only in his imagination. Not wanting to sound out of the loop, no one admits they don’t know anything about Strawberry and his work, and before long gossip has turned “The New Suit” into the most sought-after project in town, and Kevin finds himself controlling the destiny of a hot new writer who doesn’t exist. The first American film from French director François Velle, New Suit also features Heather Donahue, Paul McCrane, and Amber Smith.

The Player (1992) – Robert Altman takes a scalpel to Hollywood ethics in the 1990s (or the lack thereof) in his acidic satire The Player, adapted from Michael Tolkin’s novel. (Tolkin also wrote the screenplay.) The film concerns a sleek and smooth Hollywood studio executive who starts receiving death threats from a disgruntled writer because he has committed the ultimate Hollywood sin — he promised the writer he would call him back and he never did. This is particularly ironic because the studio executive, Griffin Mill (Tim Robbins), is considered “writer-friendly,” spending his days listening to pitches from such noted screenwriters as Buck Henry, who is pushing “The Graduate, Part II” and Alan Rudolph, who is hawking a Bruce Willis action film described as “Ghost meets The Manchurian Candidate.” But The Player finds Griffin’s comfortable lifestyle in danger of collapse. He is trying to find a way to unload his girlfriend (Cynthia Stevenson) whose independence and intelligence make her a poor candidate for a trophy wife. More importantly, it seems that Larry Levy (Peter Gallagher), a slippery executive from Twentieth Century Fox, is angling for his job. And then there are those nasty postcards and faxes from a screenwriter threatening to kill him. Altman cast over 65 stars in cameo roles as texture for his scabrous tale.

RKO 281 (1999) (TV) – Mining the controversy behind a certified masterpiece, RKO 281 is a film about the greatest film ever made — namely, Citizen Kane. With visual gusto and verbal economy, it lushly dramatizes the story of 25-year-old theater wunderkind Orson Welles, whose stunning film debut incurs the wrath of media mogul William Randolph Hearst — the inspiration for Citizen Kane’s complex and corrupt title character. Hearst’s furious campaign against the film nearly convinced the moguls to burn the negative before its release. Scream veteran Liev Schreiber plays Welles as a bullying genius, at turns cruel to his party-prowling screenplay writer Herman Mankiewicz (John Malkovich) and condescending to his sympathetic RKO studio boss George Schaefer (Roy Scheider). Director Benjamin Ross, inspired by the American Experience documentary “The Battle Over Citizen Kane,” frames the story as a battle of colossal egos — Welles, the artist, versus Hearst (James Cromwell), a bitter patrician on the brink of bankruptcy. He doesn’t stray much into Citizen Kane itself or the political atmosphere of the time and keeps the ride taut. That, and the wonderful performances by Melanie Griffith as Marion Davies (Hearst’s mistress) and Brenda Blethyn as gossip crone Louella Parsons, make it a ride well worth taking.

Swimming with Sharks (1994) – Originally screened at Telluride as The Buddy Factor, Swimming With Sharks is an uneven but engrossing picture and a possible warning to anyone with plans to break into the motion-picture business. When Guy (Frank Whaley), a recent film-school graduate with big ideas, takes a job as assistant to major studio executive Buddy Ackerman (Kevin Spacey), he believes his ship has finally come in; little does he know it’s a slave ship, for his boss is indeed worse than a slave driver. Buddy delights in abusing his boy-toy (exemplified by the scene in which he forbids Guy to go to the bathroom as he pours water back and forth from a glass to a pitcher). Meanwhile, Guy struggles to push his idea for a script and feels he’s finally made it when Buddy congratulates him on a job well done. However, much to his chagrin, his conniving boss actually takes sole credit for the project, pushing the young assistant to wit’s end — he breaks into Buddy’s Beverly Hills showplace and takes him hostage, then proceeds to torture him in a number of demeaning and horrifying ways. The whole film stands as a sort of parable about the value system in Hollywood and the cost of reaching the top; it doesn’t play like real life, but it’s not supposed to. The real reason to watch the film, however, is Spacey’s performance. He manages at once to be terrifying, hateful, and hilarious, and he makes Buddy Ackerman a character the audience won’t soon forget.

“Entourage” (2004) – Like Larry David’s Curb Your Enthusiasm, the HBO series Entourage offers a knowing and quasi-satirical inside look at the world of show business within a faux “documentary” format. Premiering July 18, 2004, the series (initially titled Sundance Kids) stars Adrian Grenier as Vincent Chase, a young, wealthy, and very “hot” movie star. As Vincent’s hard-working agent Ari Gold (a character based on real-life agent Ari Emmanuel and here played by Jeremy Piven) tried to keep both his client and his client’s career on the right track, Vincent tended to ignore Ari and pay more attention to three buddies from his old Queens neighborhood, who formed the “entourage” of the title. Vincent’s stepbrother Johnny (Kevin Dillon), aka “Drama,” made no secret of his intention to use Vincent’s success to further his own acting career, while his pal Turtle (Jerry Ferrara) was content to parasitically luxuriates in Vincent’s lavish lifestyle. Only his friend Eric (Kevin Connolly) seemed to like Vince for himself and not for what he could mooch off him — and not surprisingly, Eric’s advice and demonstrations were frequently ignored in favor of the sycophancy of Vince’s other pals. Entourage was co-created and executive-produced by actor Mark Wahlberg, who was one of several A-list celebrities appearing as “themselves” in the course of the series.

Honorable Mentions

Film School Confidential (2002)

The Kid Stays in the Picture (2002)  

“Dinner for Five” (2001)

“Film School” (2004)  

“Inside the Actors Studio” (1994)

“Project Greenlight” (2001)

“Sunday Morning Shootout” (2003) 

Which ones did we leave out?

Which ones did we get wrong?

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