5. Ed Wood (1994)
Easily one of Tim Burton’s most acclaimed films, Ed Wood is about the love of filmmaking in its purest form. The director whom the movie is based on (and named for) is popularly called the “worst filmmaker of all time.”
In technical and aesthetic terms, Plan 9 From Outer Space and Glen or Glenda are bad movies, sure, but there is a clear and determined passion behind them. Ed Wood is certainly an auteur, and his films were singular visions. This film cheers on the dogged self-reliance and unimpeachable love that went into Wood’s movies.
Screenwriters Scott Alexander and Larry Karaszewski, known at the time solely for Problem Child and its sequel, wanted the opportunity to write more ‘adult’ screenplays, and this was their first foray. The writing team would go on to make the “adult-themed biopic” their genre of choice, penning The People vs. Larry Sanders, Man on the Moon, Auto Focus, and 2014’s Big Eyes.
Their script often goes out of its way to remain sympathetic, and even though some of the film’s funniest moments are at the expense of the shoddy craftsmanship of Wood’s films, it never loses that feeling of immortal optimism, and the overall sense is that the filmmakers admire Wood despite his apparent lack of natural talent or technical acumen.
Burton’s expressionist influences get to have a lot of fun here, due in large part to the choice to shoot black and white (a decision that would cause the production to switch studios in order to go ahead with it). The photography is one element of their homage to Wood and other B-sci-fi filmmakers of the era, and cinematographer Stefan Czapsky, who had previously collaborated with Burton on Edward Scissorhands and Batman Returns, does truly beautiful work here.
The film’s accuracy is questionable (though Burton admits that was never his aim), as the offbeat comic tone of the final product can’t help but be slightly unreal. It is a generous and kind portrait of a man and his moviemaking troupe. Burton explains it best himself: “The is a sincerity to them that is very unusual, and I always found that somewhat touching. It gives them a surreal, weirdly heartfelt feeling” …much like this film does.
4. Bowfinger (1999)
This is a big, goofy comedy about a struggling movie producer with the unfortunate name Bowfinger (Steve Martin) who needs a celebrity to helm his next film in order to get the funding to film his masterpiece: Chubby Rain (the greatest title for a fake film ever?). He could never get one, of course, but fortunately he has a not-at-all-ridiculous backup plan that is sure to work: hire a lookalike.
Lucky for him, the cosmos loves Bowfinger, and the stars align when he discovers Jiff — a man who just happens to look exactly like Kit Ramsey, the biggest movie star on the planet (both played by Eddie Murphy).
It comes to mind that for Steve Martin and Eddie Murphy, this is one of their last great, broadly comic films that wasn’t aimed at a family audience. They both get to toy around in the personas that made them famous; Martin as the arrogant goofball, the huckster, and Murphy gets to repeat his successes in playing multiple characters.
Ramsey is a paranoid and possibly disturbed man, whereas in contrast Jif (Ramsey’s lookalike) is a sweet, dopey dork. It is a great treat to watch these two legends having fun at this stage in their career.
As in a lot of films presented in this list, there is a lot of Ed Wood here in both the content and quality of Bowfinger’s opus Chubby Rain. But there is less a sense here that the love is pure. Bowfinger is an opportunist, and the film more or less creates a nice redemption arc as he comes to love and support his actors and his crew. None of that matters, though, because this is just wall-to-wall laughs.
The script is smart and full of jokes. Great jokes! And Heather Graham. Remember Heather Graham? She’s fantastic! For a list of funny films about filmmaking, this is requisite, and easily one of the funniest.
3. Swimming With Sharks (1994)
The star of Swimming With Sharks is very much the main attraction here: Kevin Spacey is one of those actors we love to watch chew the scenery. He is more than capable of nuance, but he may be at his best when you give him a character with a large presence and a sharp tongue.
“House of Cards” is very much the culmination of this persona, and yet for someone who has made a career as a leading man, some of his most memorable performances have been in supporting roles. Seven, The Usual Suspects, The Ref and Glengarry Glenross are smaller roles (he doesn’t even appear in Seven until the climax) that manage to steal the movie.
Like your James Spaders and Bradley Whitfords, he has a waspy, elitist quality that is best when directly served by the story. Often that means placing him in the role of the antagonist. His casting as Lex Luthor in Superman Returns seemed almost too on the nose. In Swimming With Sharks, he gives us the quintessential Kevin Spacey performance as the vile, abusive authority figure — a role he would take up again in recent years with the Horrible Bosses movies.
You could almost see this play out like a re-interpretation of the classic noir Sweet Smell of Success. Spacey is in for Lancaster, Whaley for Tony Curtis, and the movies for newspapers.
The point of view is similarly misanthropic, and they both have a contemptuous sting to their dialogue. Naïve young screenwriter Guy (Frank Whaley) wants to make it in the movie business and ends up nabbing a job as the personal assistant to a successful movie mogul. Buddy (Spacey), however, is the epitome of the boss from Hell.
Spacey’s Buddy is a monster. He’s mean and petty, insulting and borderline criminal. He screams in his face and belittles him in public. We know he’s a villain, but it’s just so fun to watch him be such a jerk. Writer and director George Huang is merciless with his unabashedly cynical lampooning of Hollywood through Buddy, and that is taken to its inevitable, scathing conclusion by the film’s final scenes.
2. Sherlock, Jr. (1924)
Buster Keaton started performing with his family on the vaudeville stage as early as 3 years old. His part in the family act was very physical, and he would literally be thrown around the stage by his dad. Physical comedy became his forte, a natural sense of timing and the learned skill of a stunt man. He keeps his plots simple, focusing his creative energy on his ingenious set pieces. Sherlock Jr. begins with a simple story of an aspiring detective, the girl he falls for, and the villain who gets between them.
In a plot that is in the running for ‘sparest love triangle of all time,’ the bad guy steals a pocket watch from the father of their mutual object of desire. When our hapless protagonist decides to show off his skills as an amateur sleuth, the villain frames him for the theft, and gets him thrown out of her family home.
And yet none of this is what makes this movie great. Our hero works as a projectionist at the local cinema. After being rejected, he goes to work his shift, and falls asleep as the movie plays. This is when Sherlock Jr. goes from pleasant comedy to unequivocal classic.
He falls asleep while playing the latest film, and one of cinema’s great silent comedians proves that he was also a clever filmmaker. He dreams that he enters the film through the screen, and the side characters become the girl, the father, and the villain. In his wish fulfillment, he gets the chance to redeem himself and be a hero inside the plot of the film.
This is as formally inventive as it is funny. The interplay between reality and his dream is great fun, many of the most impressive special effects created with the simple stop trick effect.
This is a technique [possibly] first used by George Méliès in A Trip to the Moon, achieved very simply and quite convincing if done right: the actors all freeze, the camera stops rolling, changes are made to the frame (remove a character, add an object, etc.), and when the camera rolls again it appears as if those changes were instantaneous (like “I Dream of Jeannie,” when she would make something appear/disappear with the wriggle of her nose).
It is because of Keaton’s singularly laconic style, combined with his note-perfect sense of comic timing, that made him a star, and managed to make many of his best films remain timelessly appealing. That timing was even more impressive considering how many times he was almost maimed or flat out killed during filming his more elaborate action scenes (he was the Jackie Chan of his day; or, more accurately, you can see the huge influence Buster Keaton had on the action star).
Sherlock Jr. is brisk at only 45 minutes, and not a minute is wasted. If you have any friends who think they would hate silent movies, or if you may feel that way yourself, this is a really great entry point.
1. Adaptation (2002)
Charlie Kaufman’s writing is always high concept, usually meta-textual, and pitched with a sly smirk. Adaptation is arguably his quintessential work (you could argue Synecdoche, New York, but it was less universally loved).
This is a masterpiece so self-reflexive that it all but implodes in on itself by the time it comes to a close. He teamed up again with Spike Jonze, the perfect stylistic match for his writing (with a close second for Michael Gondry). It is claimed Fellini’s 81/2 is the only film to have itself as its own subject, but with this, they number at least two. The story of the making of Adaptation is, also, the story in the film itself.
Kaufman was hired back in the mid-90s to adapt “The Orchid Thief” by Susan Orlean, a non-fiction book about horticulture and rare flowers. A strange choice for a big screen adaptation as it is, Kaufman reportedly had difficulty figuring out how to tackle it.
His reaction was to make the movie about himself and a made-up identical twin brother (who shares writing credit on the film and holds the unique distinction of being the only fictional person nominated for an Academy Award) and his failed attempts at adapting this book.
Swaths of the film are dedicated to a legitimate adaptation of “The Orchid Thief” starring Meryl Streep and Chris Cooper, while also telling a larger story about Charlie having writer’s block. Meanwhile, his brother Donald decides to become a screenwriter, too, and finds some success after attending a Robert McKee seminar. This frustrates his brother, who sees his brother’s attempts at writing as hacky and not serious.
The McKee seminar is one of the funniest scenes in the film, and it is clear what the real life Kaufman thinks of McKee’s screenwriting “bible.” Nicolas Cage gives arguably his greatest performances as both Charlie and Donald, two nuanced and subtly different performances that take full advantage of Cage’s unhinged insanity and innate ability to go full throttle.
Then you add Streep and Cooper, Brian Cox, Judy Greer, Maggie Gyllenhaal and the inimitable Tilda Swinton, and the deck is thoroughly stacked. The prestigious cast is no surprise coming off the success of Being John Malkovich (same writer and director) three years previous.
The film goes much further into its critique of the studio standards of screenwriting in a third act that goes up another whole level of meta, where the adaptation of “The Orchid Thief” and the faux-real-life travails of the Kaufman twins collide in a bold, bizarrely emotional, mind-blowing climax that simultaneously sums up the film’s themes and parodies scriptwriting convention.
The trinity of Kaufman, Jonze and Cage is perhaps the perfect pairing of creative minds, and there is no better evidence than this, an hysterical, profoundly insightful treatise on the power and limitations inherent to storytelling.
Author Bio: Ryan Jeffrey is an independent filmmaker in Queens, New York. He’s been a film buff since he was a kid, and enjoys being able to talk about the films he loves and explore what makes them great.