1. Singin’ in the Rain (1952)
Gene Kelly’s solo musical number can probably cure fevers. Singin’ in the Rain is smart, energetic, and delightful. Set in 1927, it follows Don (Kelly) as a famous silent film star who used to be a humble singer/dancer before stumbling onto the big screen. Avoiding his insufferable co-star who is in love with him, he runs into talented chorus girl Kathy (the late, great Debbie Reynolds) and later finds out that a rival studio will be releasing their first talking picture, set to be a major hit. Kelly convinces his director to turn their silent film into a musical, and to dub Kathy’s voice over the screeching mess that is his co-star’s singing. It ends exactly how you expect it to, with Kathy and Don kissing in front of the poster for their next film – Singin’ in the Rain. As long as you’ve never seen Kubrick’s A Clockwork Orange, you’ll be smiling ear to ear during this entire feature.
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2. Sunset Boulevard (1950)
The classic… the beautiful… ladies and gentlemen, it’s none other than Billy Wilder. Even if you haven’t seen Sunset Boulevard, you know every beat and every cliché that it inspired, from “Alright Mr. DeMille, I’m ready for my close-up” to the smoky noir opening of a dead body paired with a sexy voice over. The story is told in flashback, with young screenwriter Joe Gillis relating the events that led to his death. Old silent-film star Norma Desmond is a symbol of classic Hollywood – glamorous, out of touch, and fading fast. The film was nominated for eleven Academy Awards, and secured Billy Wilder a place in film history.
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3. Scream (1996)
The teens in this Wes Craven slasher know all the rules… but that won’t necessarily help them. First-time writer Kevin Williamson and horror king Wes Craven teamed up to create a frightening slasher that tastefully pokes fun at Hollywood writing tropes. The meta characteristics seem heavy handed at first, what with Drew Barrymore listing scary movies over the phone, but the filmmakers cleverly choose to wink at the audience with Scream’s first onscreen death before gracefully transitioning to a high school solely attended by Gap models. Ghostface is a mysterious enough villain, and the cat and mouse sequences have more than enough suspense to make up for stiff acting and pink overalls. All in all, Scream does a fantastic job commenting on the genre and still scaring the hell out of you.
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4. The Player (1992)
Robert Altman’s The Player is a sick, dark, sneering masterpiece about the film industry. The movie begins with an eight minute, single shot opening that follows various employees at a Hollywood studio before landing on top executive Griffin Mills (Tim Robbins), who is being pitched The Graduate: Part 2 – “Mrs. Robinson has had a stroke. So she can’t talk. It’ll be dark and weird and funny, and with a stroke.” Mills has been getting death threats from a screenwriter whose script he rejected, and decides to take matters into his own hands by meeting up with the writer at a local showing of The Bicycle Thief. And thaaaaat’s when things go from dark to pitch black. Mills descends into madness and paranoia, constantly afraid of what he’s done and also selfishly concerned with the possibility of losing his job to a younger, slicker exec. The movie takes sharp turns when it needs to, but also feels eerily familiar, reminding audience’s that the only way to shed light on Hollywood is to, unfortunately, keep the cameras rolling.
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5. Hail, Caesar! (1996)
Only the Coen brothers could go from the touching, melancholy folk song that was Inside Llewyn Davis to the vibrant, ridiculous set of Hail, Caesar! It takes place in a 1950s Hollywood studio where soft-spoken big shot Eddie Mannix (Josh Brolin) has to put out fires left and right, starting with the odd disappearance of renowned actor Baird Whitlock (George Clooney). In all its fake glitz and glam, the film is still true to the Coen brothers’ best traits: there’s little narrative, no grand villain, and comically low stakes. The various movies being filmed at Capital Pictures are all enchanting, and if you’ve ever wanted to see George Clooney go two hours in a Roman regalia costume, this is the flick for you. The explanation for Whitlock’s kidnapping is way out of left field…literally…and provides such a fantastical scene at sea that it makes you wish the Coen’s could make a movie a year. “Oh, would that it were so simple.”
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6. Tropic Thunder (2008)
In 2007, Will Ferrell and Jack Black sang a duet at the Academy Awards about how sad it is to be a purely comedic actor at The Oscars, constantly watching colleagues and friends be nominated while you applaud on the sidelines. And then, one year later, Tropic Thunder happened. There are grenades, machine guns, a montage of hysterically bad Hollywood movies, a Tom Cruise cameo, gorgeously shot scenes, and stellar performances by an all-star cast. Tropic Thunder wins you over in its first five minutes, and by the end of the film, you’ll be left with your sides hurting from laughter, and your eyes a little watery from… also laughter. The movie constantly pokes fun at the film industry and its prima donna actors, who have names like “Tugg Speedman” and “Alpa Chino.” And yes, Robert Downy Jr. was nominated for Best Supporting Actor at the Academy Awards for this. Eat your freaking heart out.
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7. Hollywood Ending (2002)
Oh, Woody. In this mesh of slapstick, anxiety, and perfectly timed one-liners, Woody Allen plays a once well-known director who has slumped to Deodorant commercials in a long career lull. Finally landing a major motion picture, his nerves get the best of him and he develops psychosomatic blindness, a problem that he and his successful ex-wife choose not to mention to anybody. Hilarity ensues as Allen tries to block scenes, re-write dialogue, and choose set pieces all while bumping into objects or simply nodding. The cynicism towards Hollywood filmmaking appears at every turn, with a blind director creating a movie no better or worse than most pictures out there. It doesn’t have the depth or heart of Allen’s other comedies, but there’s something wonderfully familiar about Woody still getting to say lines like, “Sex is better than talk. Ask anybody in this bar. Talk is what you suffer through so you can get to sex.”
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8. For Your Consideration (2006)
Christopher Guest and Eugene Levy write and star in this satirical ode to Hollywood which is about the incompetent cast and crew of a new period piece (read: cheap melodrama), “Home for Purim.” The movie-within-the-movie concerns itself with a Southern Jewish family dealing with lesbianism and familial piety in the 1940s. If this isn’t enough material to make you smile, then throw in the towel and admit you have no soul. Between sensitive actors, re-writes, a rumor turned into Oscar buzz, and the line “the internet? That’s the one with e-mail, right?”, this film lovably pokes fun at the industry and uses its star studded cast to the best of its ability.
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9. Seven Psychopaths (2012)
Can we cast Sam Rockwell in everything? Who do we need to call to make this happen? Writer and director Martin McDonagh always over-delivers (In Bruges, anyone?), and this is no exception. Collin Ferrell plays a struggling writer trying to finish the titular screenplay, while his unemployed actor/petty criminal friend Billy (Sam Rockwell) gets in some trouble with a violent gangster who just wants his dog back. Cue Christopher Walken as Billy’s insane partner in crime, and you’re left with a western standoff in Joshua Tree complete with all three characters giving their input on Ferrell’s unfinished screenplay. The meta aspects of this movie are well-played and the atmosphere is superb, showing once again that McDonagh has a way with bending genres. With charming dialogue and slick acting comes a unique, action packed study in Hollywood cinema.
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10. Maps to the Stars (2014)
This satirical drama by David Cronenberg and Bruce Wagner is like a train without tracks. Packed with stars – John Cusack, Julianne More, Mia Wasikowska to name a few – and riddled with a lot of plot, this dark nod to Hollywood talent and fleeting fame has some beautiful scenes that you can sink your teeth into. A TV therapist and his overbearing wife (who is also his sister…which is fascinating?) try to control their famous, teen heartthrob son and their disturbed, schizophrenic daughter. Every character in the film has some connection to the industry, and all of them are trying to obtain personal freedom and agency, tying back to a constantly referenced Paul Eluard poem. It’s an artistic take on misery, and it’s definitely worth a watch.
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11. Barton Fink (1991)
One of the best things about the Coens’ delicate, bizarre, and thoughtful Barton Fink is that no one knows what genre to call it. A film noir? An artist’s tale? A horror? The intellect of the film comes across in literary allusions, parallels to Faulkner and Odets, and tastefully done religious themes, but the magic of the movie is in its telling. We’ve seen “playwright forced to turn screenwriter” movies before, but the twists that Fink takes are daring and exceptional. Just when you think the film is headed in one direction, it takes a hard turn into a tunnel and ends with decapitated heads. The social commentary on writing and 1940s Hollywood is done well, and audiences are left having seen something entirely unique.
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12. Contempt (1964)
Like most Jean Luc-Godard films, you’ll leave the theater feeling three times heavier than when you sat down. In his dark, dazzling Contempt, screenwriter Paul is trying to workshop his latest feature, Odyssey, while ignoring the fact that his marriage to the depressed Camille (a gorgeous Brigitte Bardot) is crumbling. Odyssey is being directed by Fritz Lang (yup, the real Fritz Lang) and its millionaire, American producer is slowly wooing Camille away from her absent husband and into his…beach house. The parallels to Greek mythology, the spectacular cinematography, and the haunting overture by Georges Delerue all make this one of Godard’s most praised pieces of art. Unfortunately, the only thing sunny about this film is the seashore.
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13. Adaptation (2002)
A movie about writing movies, Charlie Kaufman deserves every praise possible for the brilliant, moody, humorous, unfathomably unique piece of art that is Adaptation. Kaufman writes himself as the main character, a screenwriter trying to adapt Susan Orlean’s non-fiction book The Orchid Thief, and writes himself a twin brother, Donald, who has decided to move in with Charlie and “try screenwriting” as well after attending one of Robert McKee’s workshops. Charlie takes pride in his non-formulaic writing and grows angrier and angrier as Donald voices his own thoughts on writing, and soon sells a screenplay for six or seven figures. The film unravels and becomes a snake eating its own tail, with Charlie and Donald becoming classic action heroes in this now Hollywood-like production. Kaufman billed the writers as both himself and Donald, and with it being nominated for Best Adapted Screenplay (ha!), this could’ve been the first time an Academy Award would be given to a fictional person. Either way, it’s named the WGA’s 77th best movie screenplay ever written for a reason.
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14. Cecil B. Demented (2000)
If you haven’t tapped into the wacky, inky world of John Waters, this may be a solid start. The title character is a psychotic independent director who, along with his sex-crazed guerilla production team, kidnaps a spoiled A-list celebrity in an attempt to create a violent, anti-Hollywood feature. It’s a mouthful. Melanie Griffith stars as Honey Whitlock, the beloved star, who in true Patty Hearst-fashion decides she agrees with Cecil’s distaste for Hollywood after they invade the set of a terrible Forrest Gump sequel. This movie also features a sweaty Maggie Gyllenhaal delivering the line, “Hi, I’m Raven, I’m a Satanist and I’ll be doing your make-up.” It’s creepy, comical, and all-around perfect.
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15. Stardust Memories (1980)
Woody Allen’s Stardust Memories may be his most somber comedy to date. Allen plays Sandy Bates, a famous filmmaker trying to transition from simple comedies to complex dramas while facing fierce criticism from his loyal fans and fellow Hollywood types. The movie channels early Fellini, with breathtaking framing and nervous social commentary. Sandy Bates slowly spirals into a mental breakdown, complete with dipping in and out of the past to make sense of his many failed romances, but always being interrupted by his various neuroses. Woody Allen has denied that the character is at all autobiographical – for good reason too, since Bates is awfully bitter towards his audience – but you can’t help but see truth in his defeated expression when fans in the film constantly rush up to him and say things like, “We enjoy your films! Particularly the early, funny ones.” Whether autobiographical or not, Allen beautifully displays the shallowness of Hollywood and the haunting imperfections of both life and art.
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