The best movies about making movies

Quentin Tarantino loves Hollywood and the movies he grew up on, which is obvious when you watch any of his films or interviews. However, “Once Upon a Time in Hollywood” is the ultimate version of that. It’s not about the making of a specific film, but it’s largely about the career of actor Rick Dalton, as portrayed by Leonardo DiCaprio. Also, Brad Pitt beats up Bruce Lee on a movie set.

The film that screenwriter Joe Banks and faded star Norma Desmond are “working” on doesn’t get that far. Let’s just say things work out poorly for Banks before things get too far. Plus, Norma is pretty much out of her mind. You at the very least probably remember the end of this film, where Norma tells Mr. DeMille she’s ready for her closeup.

The main character in the 1950s-set Hollywood film by the Coen Brothers is not an actor or a director, but a “fixer” who keeps things moving smoothly for the studio. Along the way, we get to see several styles of old film, though the titular movie is a religious epic starring Baird Whitlock (George Clooney), a film that hits a snag when Baird is kidnapped by Communists.

Chili Palmer is a man with a dream, and that dream is to get out of the crime game and get into making film. Of course, getting out of the mob isn’t easy, even if you have found a screenplay that you think will really work thanks to a producer that owes your boss a lot of money. “Get Shorty” is based on a Elmore Leonard novel, so you know it crackles and pops, mixing violence with comedy quite nicely.

Yes, “The Artist” is a novelty in some ways. It’s a silent movie made in 2011 about the silent movie era of Hollywood. While the movie has been forgotten by many, Hollywood didn’t forget it when it came to the Oscars. The Academy Awards gave “The Artist” Best Picture, as apparently the concept of a silent film worked for the voters.

Yes, we have another Coens Brothers movie on this list. We had little choice, as both “Hail, Caesar!” and “Barton Fink” are top notch films. “Barton Fink” is particularly scathing, though, and it’s a little less about filmmaking than their latter effort. The titular character is a haughty playwright from New York who is brought to Hollywood for a chance to write a movie. Unfortunately, the studio assigns him a banal wrestling movie, and Barton gets writer’s block. Barton also has a neighbor –played indelibly by John Goodman – who may be more than meets the eye.

Speaking of satires, Robert Altman knows his way around that genre. Tim Robbins plays a movie executive who kills a screenwriter and tries to cover it up. Of course, showbiz doesn’t stop, especially when you are making a movie starring the actual Julia Roberts and Bruce Willis.

Preston Sturges decided he should make a comedy about the power of comedies. “Sullivan’s Travels”  – in a bit of meta storytelling – a movie about a comedic director who decides he wants to make a “serious” social drama. Then he realizes that comedy is just as valid as any serious film, and can be even more powerful. Even though this movie was made in 1941, some seem to have not learned that lesson just yet.

“Teen Titans Go!” is super self-reflective as a TV show, so naturally when they got to make a movie out of the show they took things to a whole new level. This is a “Teen Titans Go!” movie about the Teen Titans trying to make a movie about themselves. The show is slight and often silly and absurd, and while there is plenty of that in the movie there’s actually a sufficient storyline as well.

Charlie Kaufman doesn’t hold his audience’s hand, and “Adaptation” could confound you upon first watch. It’s one of the most meta movies ever. Charlie Kaufman was trying to adapt the non-fiction book “The Orchid Thief” by Susan Orlean, so he decided to make a movie about having trouble adapting “The Orchid Thief.” Also, he invented a twin and made him a character in the film too. While people often laugh at Nicolas Cage, he’d excellent in dual roles in “Adaptation,” which may be heady but still works.

“Singin’ in the Rain” is basically “The Artist” but with sound. It’s also about Hollywood’s tradition to “talkies,” and how that impacts silent movie actors. This one is a colorful musical, though, and it’s headlined by Gene Kelly and Debbie Reynolds. Donald O’Connor also turned heads with his “Make ‘Em Laugh” number.

You’re a struggling filmmaker looking to make a big action movie to break though. How can you do that? Well, if you’re Bobby Bowfinger, you secretly film a major movie star (played by Eddie Murphy) and tell everybody else in the cast that he’s only acting like he doesn’t know what’s going on because he’s that method. Then, you hire that actor’s twin brother (also Eddie Murphy) for the scenes where secretly filming somebody won’t cut it. Would that work in real life? Almost assuredly not. However, it works to make “Bowfinger” funny.

Like we said, any kind of movie counts here. “Boogie Nights” is Paul Thomas Anderson’s breakout film about the pornography industry in the San Fernando Valley where he grew up. The cast is fantastic, even if Mark Wahlberg now says he regrets making the movie. We’re happy it got made, though, because “Boogie Nights” is an excellent film, harrowing, exciting, funny, and sad in equal measure.

Alfred Hitchcock is one of the most famous directors even, and he has an outsized personality. People may not know what, say, Frank Capra looked like, but they know Hitch. There have been a couple movies about the legendary director, including “Hitchcock,” which stars Anthony Hopkins as the man himself. It’s about him (and his wife and collaborator Alma) during the making of his iconic “Psycho.”

We’re back to Eddie Murphy, though this time it’s a work based on a true story. Rudy Ray Moore was a comedian and musician struggling to make ends meet. Then he remade himself as a vulgar comedian, and decided to take that personality and turn it into a film. Of course, he had no idea how to make a film, but he did it anyway. “Dolemite is My Name” chronicles Moore trying to make the movie “Dolemite.” It was a real return to form for Murphy, who has made some, shall we say, questionable film choices in recent years.

“Ed Wood” makes a good companion to “Dolemite is My Name,” which is fitting because they were written by the same duo. The director Ed Wood was not as successful as Moore, but “Ed Wood” is a truly successful movie. Johnny Depp is fantastic as Wood himself, but Martin Landau won the Oscar for playing Bela Legosi.

“The Aviator” is a biopic about Howard Hughes, so it isn’t entire about making movies. However, a lot of it is. A big portion of this movie is about Hughes directing “Hell’s Angels.” Also, Katharine Hepburn is a major character, and won Cate Blanchett an Oscar. This movie is equally about aviation and filmmaking in many ways, and it’s all-in-all fascinating.

You have to really earn the right to make a thinly-veiled biopic about yourself. It’s safe to say Pedro Almodovar did that before making “Pain and Glory.” He casts frequent collaborator Antonio Banderas as his analog in a movie about an aging director who fears like his career is on the decline. Hey, if you are going to make a de facto biopic, it goes down easier if you aren’t patting yourself on the back.

“Mary Poppins” is an iconic movie, but its path to the screen wasn’t easy. The writer of the book the movie is based on, P.L. Travers, had to really be convinced to sell the rights to Disney. That’s the story being told in “Mr. Banks.” The movie doesn’t always work, but it features Tom Hanks as Walt Disney, which is one icon playing another.

David Mamet isn’t known for his light, optimistic movies. That’s clear in his film about the making of a movie, “State and Main.” It’s your classic film about compromised ideals in show business. Unsurprisingly, a guy who made his name as a playwright has a lot of sympathy for the screenwriter who is seeing his work being tinkered with – and arguably destroyed – by the filmmaking machine.

Peter O’Toole is a venerated actor. He was nominated for Best Actor eight times – though he never won – and one of those nominations came for “The Stunt Man.” What’s surprising is that “The Stunt Man” is not a searing, serious drama, but an action comedy. It’s about a fugitive who hides out by working as a stunt double in a World War I movie. Some consider it something of a lost classic.

“Matinee” seems to come straight from Joe Dante’s heart. It’s about a kid during the Cold War who meets a legendary schlocky filmmaker, Lawrence Woolsey (John Goodman). Woolsey is based on William Castle, who would use any gimmick he could think of to try and generate attention. That’s kind of the real drive of “Matinee.” Woolsey’s movie “Mant!” is pretty much ready to go. The director is really trying to figure out what kind of gimmicks he can use to hook audiences in a troubled time.

“The Room” quickly became an iconic bad movie, inspired in part by the fact the star and director of the film Tommy Wiseau seems like a truly bizarre guy. Hollywood celebrities quickly came to have an affinity for “The Room,” leading to a movie about the making of the film. James Franco stars as Wiseau, channeling the eccentricities of the avant garde filmmaker. Maybe “The Disaster Artist” isn’t as fun to watch as “The Room,” but it is clearly a better movie in the traditional sense.

“Nosferatu” is one of the iconic early horror films. It starred the German actor Max Schreck, who was very much a normal human man. That is, unless you are watching “Shadow of the Vampire.” The film has a clever premise, as it focuses on the crew of “Nosferatu” trying to figure out of Schreck is, in fact, a vampire in real life. Willem Dafoe was nominated for Best Supporting Actor for playing Schreck.

We end with a movie where a lot of movies are made. “Be Kind Rewind” is a silly little comedy, but it’s a lot of fun at its best moment. Jack Black and Mos Def play two guys who work at a video store where all the VHS tapes are accidentally erased. The duo them decide, in order to stay in business, to make their own versions of every movie to rent out. Thus, we get to see snippets of Black and Def, and others, working to remake some classic films from the past.