The seemingly infinite onslaught of comic book movies, sequels, television adaptations, remakes, and reboots make it easy to forget that Hollywood does in fact have one other favorite subject – itself. Filmmakers have been making movies about movies since the moment the medium solidified enough conventions to begin lampooning, honoring, and investigating. Surely, these films can sometimes be indulgent exercises in self-flattery. Just as often they are clever, thought provoking, insightful or flatly hilarious.

“Meta” is probably the term you hear aptly threading all these films together, a more colloquial version of “postmodern”. We are talking about art that knows it is art, films that wink at their audience as they fold in upon themselves. But we are also talking about films that are more than that – it isn’t enough just to have a character break the fourth wall for a laugh (Hi, Ferris), or be self-effacing as a quick comedic device.  These films are knowingly constructed on the foundations laid before them, and they all directly concern themselves with movies in one way or another. Some are funny, some are poignant, and still others are thrilling, even horrifying.

These are the 15 Best Movies About Movies

15. Singin’ In The Rain

Singin In The Rain The 15 Best Movies About Movies Of All Time

Singin’ In The Rain tops the American Film Institute’s list of greatest movie musicals ever made, places fifth on the Institutes list of the 100 Greatest American Films of all time, and was one of the first twenty-five films selected for the newly minted National Film Registry in 1989 – not bad for a film that was a modest hit when it was released, ranking “only” tenth that year at the North American box office.

The film, released in 1952, stars (and was directed by) Gene Kelly as a silent film star making the transition to talking pictures. The “making the transition” description of the film is the sort of one-line plot summary that is neither descriptive or just – Singin’ tells a poignant story about Kelly and his love interest Kathy, a talented singer and actress who – despite being a somebody to him – was a nobody in general until the advent of sound made her considerable talent much more valuable. She supplants the studio’s leading lady in the film’s touching climax, and Don and Kathy kiss in front of an advertisement for their new film, titled Singin’ in the Rain.

14. Barton Fink

Barton Fink The 15 Best Movies About Movies Of All Time

Barton Fink lost money, grossing six million dollars at the box office against a nine-million-dollar budget, which is fitting. The film is among the least accessible in the Coen’s oeuvre, and is thematically very conscious of that fact, or at least very conscious of the difference between high minded all-caps ART and more common, popular fare. Box office failure aside, Barton Fink was a critical darling, sweeping Cannes film festival and receiving three Academy Awards nominations.

Fans of the Coens and of this film in particular know it’s tough to describe what Barton Fink is about. Its plainly about the film business and the nature of creativity, writing to be exact. But the jumble of genre elements – ranging from comedy to horror, with a heavy amount of introspection peppered throughout – make it nearly impossible to categorize. That, coupled with the avalanche of film references included in the movie, make multiple viewings absolutely unnecessary to unpack the Coens’ statement.

Barton Fink is a film about films in general. It’s a film about other films, specifically. It’s about creating, and about destroying. It’s funny, disturbing, and confusing. It’s a must see for any fan of the Coen Brothers’ work, and a shining example of what movies about movies are capable of.

13. Get Shorty

Get Shorty The 15 Best Movies About Movies Of All Time

Get Shorty is the sort of breezy, bright, and thrilling fare that is easily and satisfyingly devourable. Whereas some films on this list use self-reference and postmodernity to build a wall in front of the audience, Get Shorty wants everyone in on the joke.

Released in 1995, the film is a star studded adaptation of Elmore Leonard’s novel, also titled Get Shorty. John Travolta stars as a mobbed up tough guy who gets involved in the movie business (the why of it isn’t necessarily important to know), alongside Danny DeVito, Gene Hackman, and 90s superstar Rene Russo. The film’s plot – unsurprisingly, given its source – is engaging, twisty, and fun.

Most of the laughs and the clever winks in the film come from the analogy drawn between the movie business and the business of organized crime. Travolta’s character, Chili Palmer, discovers that his talents easily transfer between the two, which is good because he is a bonafide cinephile. The stars in Get Shorty sparkle, and the meta elements of the film give an otherwise faithful entry to the comedy-thriller genre and added layer of sophistication and humor.

12. The Artist

The Artist1 The 15 Best Movies About Movies Of All Time

The Artist, like Singin’ in The Rain, takes place at the advent of the talkie – the two are similar in a number of ways, despite the former hitting theaters nearly sixty years after the latter. But it wasn’t The Artist’s similarity to other films that made it a critical and commercial success; it was the film’s dogged originality, despite being a black and white silent film released nearly eighty years since the heyday of the form.

The Artist centers on the romance between an older silent film leading man and a young actress, around the time that silent cinema was usurped by films with sound. Exactly the kind of movie about movies that the people who make movies love, The Artist is a naked love letter to the medium, one that critics and the Hollywood hegemony rewarded with copious praise and awards consideration. Ten Academy Award nominations, with five wins including best picture, best director, and best actor. Six Globe nominations, three wins. 12 BAFTA nominations, seven wins. It’s safe to say the film’s self-imposed limitations, a potential hurdle in 2011, were handled perfectly. The Artist is a must-include on any list of the best films about film. Oh, and it’s a heartfelt and funny romantic comedy, to boot.

11. Tropic Thunder

Tropic Thunder The 15 Best Movies About Movies Of All Time

In 2008, Robert Downey Jr did a movie almost entirely in blackface makeup – the vast majority of 106 minutes of film running time, at least – and remarkably, any controversy regarding that fact was so marginal it may as well have not existed, if it ever did at all. In fact, Downey Jr. was nominated for an Academy Award (!) for his role in the film.  Those two sentences might seem impossible, especially today’s internet outrage climate, but it’s true. Audiences got the joke, because Tropic Thunder was clever, clear enough in its cutting satire, self-deprecating, and downright funny enough to execute a true taboo in a way that had everybody laughing.

The film, directed by and starring Ben Stiller, follows a cast of actors as they film the next great war movie. Unbeknownst to them – a vapid action star, an insane method actor (Downey, who’s character is a white Australian man), a fart humor comic, and a rapper-turned-actor – the film production has gone completely FUBAR, and they are actually navigating a violent drug ring’s territory. The action is real.

Tropic Thunder is easy to digest, less clouded than some of the other films on this list; the meta element here was used to sharpen the film’s comedy claws, rather than its artistic statement. But watching a film have so much fun earnestly poking fun at itself and the industry without a hint of cynicism was contagious, at least contagious enough to warrant Tropic Thunder’s inclusion on this list.

10. Scream

Scream4 The 15 Best Movies About Movies Of All Time

Wes Craven had to walk a tight rope with Scream, creating a wryly funny send up of the horror genre without sacrificing real scares.  The result is arguably the most iconic horror film of the last two decades, one that spawned three sequels, a TV show, multiple imitators, and an entire cottage industry of spoof films.

Scream is unique in its execution. It wasn’t the first film to subvert genre conventions, but it was one of the first to plainly acknowledge that it was doing so. Having its cast of teenage characters openly sit around discussing the influences of horror movies on what was happening in the plot was an effective, if on the nose, way to inject clever humor into an otherwise gruesome story.

There is a case to be made that Scream rejuvenated the horror genre, which was flagging and over-reliant on recycled properties and sequels at the time. Subscribing to that notion is an acknowledgment that the meta elements of the film weren’t just funny, clever, and original in Scream itself; they also reminded us what we loved about horror in the first place, and that scary movies can make us do other things – think, laugh even – beside scream.

9. Adaptation

Adaptation1 The 15 Best Movies About Movies Of All Time

Adaptation is a semi-autobiographical film about a screenwriter writing a film based on a book, but becoming blocked and desperate as his life begins to intersect with the protagonists of the book he is trying to adapt. That book is The Orchid Thief, a real life work by Susan Orlean, which Charlie Kaufman was real-life tapped to adapt to the big screen, before becoming real-life blocked and writing the film that became Adaptation. Confused?

It’s remarkable that Adaptation, as layered and confounding as its premise is, turned out as funny, thrilling, and accessible as it did. Truly, a tribute to Kaufman’s singular perspective and talent, as well as the dual acting performance by Nicolas Cage as Kaufman, and Kaufman’s fictional twin brother Donald, an invention of the film.

This entry has been confusing enough now, which is a direct result of Adaptation’s complexity – it is without a doubt of the most bizarrely self-referential films on the list, a snake that eats its own tail.  It’s also one of the most rewarding and enjoyable.

8. Kiss Kiss Bang Bang

Kiss Kiss Bang Bang2 The 15 Best Movies About Movies Of All Time

Here’s and apt analogy: Shane Black is to Kiss Kiss Bang Bang as Wes Craven is to Scream. That is to say that Black took the buddy-action-comedy genre – one he largely helped architect – hung it upside down and shook out its pockets.

Kiss Kiss is remembered favorably for many reasons. It was a crucial step in the Downey Jr. comeback tour, which culminated with his inspired casting as Tony Stark. It was something of a comeback for Black himself, who had fallen out of vogue a decade prior.  It gave us a fantastic Val Kilmer performance, and eminently quotable lines. More than anything, it was the film’s snarky self-reference that endeared it to the cult audience it would eventually accrue.

Downey Jr. gives a typically charismatic and self-deprecating narration of the film, at times even stopping mid frame to explain a convoluted plot point, or lament that a certain plot twist was so cliché.  From start to finish, the film is smart: it’s a thrilling mystery with unseen twists and turns and memorable characters spitting out great dialogue. That Kiss Kiss Bang Bang not only takes place in the film industry but acknowledges itself as a send-up only made it cleverer, without ever becoming too smart – or cool –  for its own good.

7. Bowfinger

Bowfinger Stars The 15 Best Movies About Movies Of All Time

Leave it to Steve Martin to make an Eddie Murphy film in 1999 that was witty, funny, and completely devoid of fat suits. Bowfinger did put Murphy in two starring roles, and there were some prosthetics involved, but again this was Eddie Murphy in 1999. Those tired gimmicks aside, the film was an overall success. It nearly doubled its budget at the box office, and managed to woo critics as well, who largely found the film to be sharp and hilarious.

Both Murphy and Martin worked well in the film, which Martin penned. Bowfinger is about a low level film producer (Martin) with no money who hatches a scheme to film a movie starring a high profile actor (Murphy) without the actor’s knowledge. There are some plot mechanics here that are long and convoluted, but his plan works for a time. Until Ramsey, the actor, snaps and goes underground. So Martin’s character, Bowfinger, hires a lookalike to stand-in for Ramsey.

The film takes aim at actors, filmmakers, and Inside-Hollywood targets like The Church of Scientology – well, to be fair, it hasn’t been acknowledged that Scientology was the inspiration for some of the film, but it would be a strange coincidence. That aside, Bowfinger manages to maintain a playful tone while picking at the movie business, making it an earnest and hilarious achievement.

6. Blazing Saddles

Blazing Saddles The 15 Best Movies About Movies Of All Time

Blazing Saddles is rightly remembered as one of Mel Brooks’ crowning achievements, a western-style satire that was fearlessly offensive. It should also be remembered as a film that turned breaking the fourth wall into actual demolition. Other movies can keep their winking protagonists and aw-shucks turns to the camera, Blazing Saddles actually ended with the cast smashing through a studio wall into a neighboring set, and eventually out onto a studio lot and into the famous Grauman’s Chinese Theater in Los Angeles.

Brooks’ film goes further than one neat little trick in its lampooning of cinema. The western genre and racial film stereotypes are both under fire from the opening credits, and the film doesn’t pull any punches.

Mel Brooks was a filmmaker who loved to draw attention to the joke at hand, whether it is the fight scene in Blazing Saddles that spills over to a musical, or the Spaceballs merchandise references in Spaceballs. Or The Producers on the whole; but you can tell that despite targeting film in many of his works that Brooks is both an avid student and ardent fan of all of cinema.

 5. Seven Psychopaths

Psychopaths Cast The 15 Best Movies About Movies Of All Time

Seven Psychopaths is the second collaboration between screenwriter-turned-director Martin McDonagh and Colin Farrell, the first being In Bruges. If you’ve seen the latter (or McDonagh’s other major film, The Guard) you should have some idea of what to expect to Seven Psychopaths, which stars Sam Rockwell, Woody Harrelson, Christopher Walken, and Tom Waits alongside Farrell.

The plot follows a struggling writer in Los Angeles (Farrell) who is trying to complete a screenplay called Seven Psychopaths. We don’t want to spoil the plot of the film for you if you haven’t seen it. Just take our word that, like any good metafilm, the film grows layers that fold in on one another, as Farrell’s screenplay fiction begins to intersect with the film’s reality and fireworks ensue.

For fans of In Bruges’ dark tone and humor, Seven Psychopaths is a must-watch. The film does more than deftly poke fun at the creative process and the art of filmmaking; it mixes tone and genre elements in a way that makes for a truly rewarding and hysterical viewing experience.

4. The Player

The Player The 15 Best Movies About Movies Of All Time

The Player is Robert Altman’s Hollywood satire about a studio executive (Tim Robbins) who goes to work each day to listen to film pitches and decides which get the green light. In addition to the stress of his job and work environment, the executive is receiving postcards with death threats, probably from a rejected screenwriter, and probably from one screenwriter in particular.  Exec and writer meet, a fight ensues, one of the two doesn’t make it, and the comedic mystery takes off from there.

The Player was both something of a personal statement and a reemergence into studio pictures for Altman, who had sort of only nibbled at the periphery of mainstream culture in the decade or so beforehand. As such, it is something of an outsider’s satire, despite the loads of actors who make cameos in the film. There is a cynicism and a tinge of darkness that pervades The Player without ever turning to a bitterness that could kill the considerable humor of the film. It is a definitive Hollywood satire, and one of the best movies about the movies ever made.

3. Argo

Argo The 15 Best Movies About Movies Of All Time

We’ve already alluded to the idea that the people who make movies generally reward movies about the ‘power’ of movies. That power could be soft, a general sense of dignity inherent to the medium. It could also be hard power, about what film can tangibly affect. In that second category, all the way at the logical extreme, lies Argo.

Argo is a political thriller that is only tangentially about movies in tactile terms, but is very much about the idea of film as a benevolent enterprise. The film is based on true story of a CIA rescue of six American diplomats in hiding in Iran. In order to exfiltrate the group, CIA officials created a dummy Hollywood film and moved them, with the help of an operator (Ben Affleck), out of the country, posing as a Canadian film crew.

Argo is thrilling and unbelievable, despite being true to life. And the suspenseful, white knuckle sequences in the movie are handled with great care. The film also goes to great lengths to depict the Hollywood con, bringing Alan Arkin and John Goodman as a studio exec and makeup man who give the fake film some credibility. It’s in those scenes that Argo reveals itself to be not just a capable thriller, but also a wry satire of the filmmaking process.

2. Mulholland Drive

Mulholland Drive1 The 15 Best Movies About Movies Of All Time

Mulholland Drive was directed by David Lynch, which should give you some idea of how difficult it will be able to describe in this space. Like much of Lynch’s work, there is a ton at play in the film, which defies categorization or description. On the surface, Mulholland Drive is about a bright young actress who arrives to Los Angeles only to find herself in the middle of a dark mystery. However, the narrative plays with time and reality, eventually revealing that what you, the viewer, thought was real may not have been after all.

Lynch’s feeling toward Hollywood in the film is as difficult to unpack as the plot itself. Mulholland Drive isn’t postmodern to be clever, or funny. You really feel as though the filmmaker is saying something definitive about the city of Los Angeles, the film business, and the destructive effect that both can have on a person’s psyche. Mulholland Drive is one of the most challenging films on this list, but is also a singularly powerful statement about the art form itself.

1. Blow Out

Blow Out The 15 Best Movies About Movies Of All Time

Blow Out was a box office failure, grossing twelve million dollars against a budget of eighteen million, and proving (like some other films on this list) that not all meta-movies are received equally. Still, the film was mostly favored by critics, and has assumed something like cult status in the thirty-five years since its release.

Blow Out was written and directed by Brian De Palma, and stars John Travolta as a sound engineer working on low budget films. While collecting some extra sound effects at a park, Travolta’s character unwittingly records the sound of a crime and becomes engulfed in a conspiracy that grows as the film progresses.

Blow Out stands out on this list as the film probably most concerned with the nuts and bolts elements of film making itself, and the power of that process to shape reality. Travolta’s character in the film brings viewers on a deep dive into the technical mechanics of movie making, mechanics that prove crucial to the film’s plot. Like much of De Palma’s other works, Blow Out is a mish-mash of influences, call-backs, and references, a feast for film lovers to pick through and enjoy. As films about film go, you would be hard pressed to find a more meta offering than Blow Out.

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