It’s only natural that Hollywood has had a long love affair with making movies about movies---what’s surprising is how compelling movies about movies can be. Seeing the gears within the machine is entirely entertaining, whether it be a championing celebration or the ridiculousness of it all. In that way, the subgenre spans a huge swath of kinds of films from the very beginning of the industry to the biggest films today. This is even shown in the first two versions of A Star Is Born, which are among the best looks into the Hollywood industry at the time they were made, with 1937 coming out of the silent film era and 1954 at the height of the Hollywood movie musical. With the ever-changing industry, films about filmmaking will always have fresh things to say. These five films now streaming on Netflix and Fandor couldn’t be more different takes on the same subject, with all products of the times.

Sherlock Jr. [Buster Keaton, 1924]
Available on Fandor

Two weeks in a row recommending a Buster Keaton classic, but can you blame me? In Sherlock Jr. the stone-faced acrobat plays one of the movies’ most underappreciated roles: the projectionist. He’s not exactly a sterling professional, however, falling asleep during a screening which leads to a dream where he literally enters into the frame. During the movie within a movie within a dream, the projectionist becomes a brilliant detective [hence the title] who must save his true love. Sherlock Jr. is Keaton’s most innovative narrative and a whole lot of fun. As always, Keaton shows off his incredible physical comedy, capping it off with an impeccably coordinated high speed stunt---Keaton races through traffic, over bridges, across train tracks at high speed while sitting on the handlebars of a motorbike. Sherlock Jr. is a love letter to the big dreams movies can inspire and how we want to inhabit the lives of our greatest heroes. But in Keaton’s signature way, the rip-roaring entertainment keeps it from being too sentimental.

Sunset Boulevard [Billy Wilder, 1950]
Available on Netflix

One of the great films from classic Hollywood, Sunset Boulevard shows the dark side of fame as well as any film. Former silent film star Gloria Swanson plays faded former silent film star Norma Desmond, a psychotic shell of her former glamorous self. She gives a towering performance, one of the best during an era full of colorful characters. As failing screenwriter Joe Gillis [William Holden, always a reliable leading man] is welcomed into her life to write a final starring role, we get a peek into the depressing, bleak life of a person left behind by the system. In a nice touch, great filmmaker Erich von Stroheim, who directed Swanson’s most notable previous work Queen Kelly, plays Desmond’s only confidant. Though it may not be the most cheery look at the industry, Sunset Boulevard is full of wonderful insights, name drops, and inside jokes. To bring this list together, Buster Keaton makes a notable cameo as himself, now a similarly left-behind star long forgotten once the talkies took over.

Modern Romance [Albert Brooks, 1981]
Available on Netflix

Not every film about Hollywood has to be primarily focused on the industry. Take Albert Brooks’s slightly bitter comedy Modern Romance, which is first-and-foremost a moody romantic comedy with particular insights into moviemaking. Brooks stars as Robert Cole, an editor with relationship issues. The film’s central on-again-off-again romance is played mostly straight, aside from Brooks’s neurotic tics, leaving most of the comedy to the Hollywood workplace subplot. As an editor who doesn’t have as much say on the types of projects he can work on, Cole is stuck on a comically terrible looking science fiction film being directed by a hack [played by real-life filmmaker James L. Brooks]. The brief looks we get into the fictional film serve as a sharp parody of the big-budget fantasies that began cropping up after the success of Star Wars. Brooks has long been an unappreciated director who is getting a first or second look from a lot of film lovers with all his directorial work recently hitting Netflix streaming---another Hollywood-set story available is the struggling screenwriter comedy The Muse.

Lost in La Mancha [Keith Fulton & Louis Pepe, 2002]
Available on Netflix

When considering films about filmmaking, you can’t leave out the many great documentaries about making films---there are even some great docs about films that never got made. Back in 2000, Terry Gilliam attempted to adapt Cervantes’s masterwork as The Man Who Killed Don Quixote, and he failed miserably. Though it was meant to be a straight-forward “making of” companion film, Lost in La Mancha struck gold to chronicle the chaotic production. Already known for a famous battle with the production studio over final cut of his eventual masterpiece Brazil, Gilliam completely lost control over the ambitious project once the budget was cut and many unforeseen hazards popped up. Ultimately, the film strikes an incredibly sad chord, showing just how difficult it is for even the most talented and passionate filmmakers to get a movie made. Lost in La Mancha is particularly relevant with the recent news that Gilliam is giving the film another attempt with shooting scheduled to begin in October. I wonder if anyone is considering a sequel...

Somewhere [Sofia Coppola, 2010]
Available on Netflix

The daughter of Hollywood royalty [now Hollywood royalty in her own right], Sofia Coppola brought the Hollywood subgenre together with her slacker subgenre style. In Somewhere, A-list star Johnny Marco, fresh from rehab and without passion for his work, is visited by his pre-teen daughter [and early role for Elle Fanning]. Like Coppola’s breakout Lost in Translation, the film examines how a male actor with his best days behind him reevaluates his life in the presence of younger muse. Unlike the other films on this list, Somewhere reflects modern Los Angeles: laid back, sunspotted, and a bit melancholy. Stephen Dorff stars as Marco, in what was supposed to be the real-life struggling actor’s reemergence---but unlike the push Bill Murray received for his collaboration with Coppola, Dorff unfortunately didn’t gain much traction as the film underperformed with audiences and critics. Still, Coppola’s unique view of Hollywood and personal aesthetic make for an interesting mix of cool and sad, with Dorff the perfect mirror for that mood.