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22 Essential Films About Hollywood

22 Essential Films About Hollywood

Last week, we riffled through the films of Joel and Ethan Coen and assembled our ranking of the 65 best Coens characters. Today, we pay tribute instead to the spirit of their newest film “Hail Caesar!” by running through some of our favorite films on the same topic: Hollywood and the follies and foibles of the world’s most famous industry town.

Almost as long as there’s been a “Hollywood” — a part of Los Angeles that is synonymous with the movie industry and especially with the studio system that perseveres in one form or another to this day — there have been filmmakers who wanted to take it as their subject. And almost always, those films have contained more than a hint of caution. When Hollywood takes a hard look at itself, it rarely has any illusions that it is the Tinseltown dream factory of lore.

And it rarely sees itself as anything but dazzlingly white. Unsurprisingly, in light of the recent diversity controversies that the Coens themselves have been challenged on in relation to the casting of “Hail Caesar!,” It should be noted that the majority of films about Hollywood, with only a few notable exceptions, are overwhelmingly concerned with travails or follies of white people. In a way, that’s an honest approach: Hollywood has been a place not only lacking in diversity, but also where issues of racist representation or ethnic exclusion have to date been essentially unimportant to the powers-that-be, and so go unremarked on even in films that critique the industry in every other way.

READ MORE: The 100 Most Anticipated Films Of 2016

Diversity issues aside, it’s a surprisingly massive category, so to narrow it down a bit, and in keeping with the broader, ensemble-based approach of “Hail Caesar!”, we’ve largely avoided biopics like “The Aviator” and “Gods and Monsters.” And we’ve tried to focus on films that have a wide-angle take on the industry, as opposed to being primarily about, say, writers, like “Adaptation,” and we’ll keep Hollywood documentaries for another feature all to themselves someday.  Bearing all those criteria and caveats in mind, here are 22 titles from the many hundreds that exist that we admire or love to varying degrees and which illuminate the nature of the Hollywood myth through the ages. 

“Sunset Boulevard” (1950) 
It was made over 60 years ago, but Billy Wilder’s “Sunset Boulevard” already feels like an end-of-empire take on Hollywood (“Hollywood’s like Egypt. Full of crumbled pyramids. It’ll never come back,” David O. Selznick would say the following year), made as the first wave of moguls, stars and directors were starting to die away. Wilder’s poison love letter to the business (in more than one sense: the film resulted in the end of his collaboration with writing partner Charles Brackett) sees deadbeat screenwriter William Holden stumble across forgotten silent star Norma Desmond (Gloria Swanson), who hires him to rewrite the “Salome” biopic she sees as her path to stardom. Bar perhaps “Ace In The Hole,” it’s as cynical a movie as the famously cynical Wilder ever made, an investigation into the ruthlessness, delusion and madness of fame. Although Hollywood history was at the time only a few decades old, Wilder steeps his film in it, shooting the hills, backlots and homes of the movie business like few before or since, and including cameos from the likes of Cecil B. DeMille, Buster Keaton and, picking up an Oscar nod, Erich Von Stroheim. But Swanson towers above them all, taking a character that she had plenty in common with, and turning her into something closer to a great Universal Studios movie monster. 

“The Stunt Man” (1980)
Completely preposterous from beginning to end, wildly uneven in tone and intent, and full of exactly the kind of lies and tricks it purports to expose, somehow “The Stunt Man” from director Richard Rush (“Freebie and the Bean“) is a blast. The story is poppycock: a young drifter on the run from the cops (Steve Railsback, who four years before had been freakishly perfect cast as Charles Manson in the “Helter Skelter” TV movie) causes the death of a stuntman on the set of a big Hollywood production, and by an unlikely series of circumstances ends up replacing the dead man, falling for the leading lady (Barbara Hershey) and clashing with the mercurial, magisterial director Eli Cross (Peter O’Toole). It falls to O’Toole to account for the story’s more deranged turns by essentially embodying an impossible character: a genius-level, all-seeing, hyper-manipulative, insidiously charming, egocentric madman —i.e. a Hollywood exaggeration of a Hollywood director. And wouldn’t you know it, he pulls it off. This is O’Toole’s film, in which he manages to sell the vague plausibility of this extremely implausible man through sheer force of charisma. Perhaps inevitably, it coils through one too many twists before it ends, and the interest level plummets whenever O’Toole is not on screen (though Hershey has her moments). But for the most part, this is a terrific showcase for O’Toole’s suavity and an enlightening snapshot of the myths Hollywood likes to create around itself and its personalities.  

“The Player” (1992) 
The premise was obvious; Robert Altman taking an all-star cast and doing for the movie business what he did for country music and politics in “Nashville.” But “The Player” proved to be a slightly different proposition, a more tightly-focused satirical noir from writer Michael Tolkin that doesn’t quite sit alongside the director’s very top-tier work, but is still thoroughly enjoyable. Opening with a bravura, “Touch Of Evil”-evoking tracking shot, the film tracks studio executive Griffin Mill (Tim Robbins, in the kind of bland-exterior dark-interior turn he does so well), who’s afraid for his job, is being stalked by a mysterious figure and ends up murdering a screenwriter (fulfilling the nightmares of most writers and the dreams of most executives). As far as Hollywood neo-noir goes, it isn’t “Sunset Boulevard,” though it has a few surprises in store —the moment where Mill confesses to his victim’s girlfriend (Greta Scacchi) who he’s been sleeping with, only for her to tell him she loves him, is sharp. And the film never quite has the satirical bite you want it to have. But from the plentiful cameos to the in-jokes, which have managed to age remarkably well, it’s an entirely pleasurable experience, one that ironically helped return Altman, who’d been in the wilderness, to the top. 

READ MORE: 10 Robert Altman Films You May Not Know

“Hollywood Shuffle” (1987)
Probably the best corrective to the Hollywood movie’s blinding whiteness, given that Spike Lee’s “Bamboozled” (aside from this great montage) is more focused on the television industry, is this scattershot but heartfelt, highly entertaining film from Robert Townsend (“B.A.P.S.” “Eddie Murphy: Raw“). Starring Townsend himself (who co-wrote with Keenan Ivory Wayans), it’s a collection of vignettes, dream sequences and extended sketches based on his own struggles as a black actor trying to make it in Hollywood. Townsend plays Bobby Taylor, who frequently skips out on his hot-dog restaurant job to go to auditions and who dreams of winning his fifth Oscar and playing the lead in a film noir-style detective movie. Instead, he is inevitably trying out for jive-talkin’ pimp roles or other such stereotypes, (which are a long way from his mild-mannered, well-brought-up, supportive-family-and-loving-girlfriend experience) and often asked to be “a little more Eddie Murphy.” In a kind of “be careful what you wish for” scenario, he eventually lands a part that might make him a star, but only if he plays up to all those corrosive black stereotypes. The film would be a blast of pointed fun if only it weren’t so depressing that it was made nearly 30 years ago, and most of its observations about race in Hollywood still sting today. As “Birth of A Nation” actor/director Nate Parker said only recently: “As a black man, you leave auditions not hoping you get the job, but wondering how you explain it to your family if you do.”

“Singin’ In The Rain” (1952)
At once a love letter to the Hollywood musical and arguably its finest example, “Singin’ In The Rain” was bafflingly only a middling hit upon release and was mostly ignored by the Oscars. 63 years on, Stanley Donen’s film is cemented as a classic, one of the funniest, most romantic and most loving pictures that Hollywood ever made about itself. The film came from unambitious origins —it’s essentially a jukebox musical, intended to showcase songs from classic MGM musicals of the 1930s. But from modest beginnings, Donen and writers Betty Comden and Adolph Green spun gold with their story of the attempt to convert silent period picture “The Dueling Cavalier” into a talkie after “The Jazz Singer” brings sound to the movies, though leading lady Lina Lamont (an Oscar-nominated Jean Hagen) has a voice that sounds like nails on a chalk board. It’s not exactly thickly plotted —as with the best musicals, there’s just enough to sustain some laughs (and there are plenty), a romance (between Gene Kelly’s dapper star and the utterly winning Debbie Reynolds) and, most importantly, music numbers. And what numbers, with the title tune providing one of film’s most iconic images, and Donald O’Connor’s bravura “Make ‘Em Laugh” one of its funniest. Right up to “The Artist” and, yes, “Hail Caesar!,” the film more or less defines the way that Hollywood idealized itself at the time, and you couldn’t blame a film this joyful for doing just that. 

“Maps To The Stars” (2014) 
He has one or two studio movies on his resumé (“The Fly” being the most notable), but David Cronenberg has remained a resolute outsider for the most part, which makes him the perfect candidate for exposing Hollywood’s rotten heart in “Maps To The Stars.” And then to set it on fire. Written by Bruce Wagner, the film focuses mostly on the Weiss family —celebrity psychologist Stafford (John Cusack, the start of the Cusack-aissance that would continue with “Love & Mercy”), stage-mom nightmare Cristina (Olivia Williams), the badly burned Agatha (Mia Wasikowska) and bratty child star Benjie (Evan Bird), while fading movie star Havana (Julianne Moore, who won Best Actress at Cannes for this film, and arguably does better work here than in her Oscar-winner “Still Alice”) and limo driver Jerome (Robert Pattinson) are brought into their orbit. It’s a little woolly in the plotting and is decidedly more disposable than the best of Cronenberg’s work (perhaps fittingly, for a film about the superficiality of Hollywood), but it manages to get into the heart of Los Angeles and the business that drives it. It’s less a satire than a grotesque, gothic Greek tragedy, more Sam Shepard than Sunset Boulevard.”

“Sullivan’s Travels” (1942)
One of Preston Sturges‘ most influential films (the Coens’ own “O Brother Where Art Thou?” is named after the fictional script within the film), this classic comedy is one that surely Sullivan (Joel McCrea) himself would have loved to have made. Solving the problem the film gives to its characters, that of comedy versus social relevance in moviemaking, by simply choosing to be very funny and very socially aware at the same time, Sturges’ picture is also a delightful reminder that the Hollywood prejudice against comedy as awards-worthy or “important” dates all the way back to the Golden Age. Following the successful but disillusioned Sullivan as he opts out of a plush Hollywood lifestyle earned by directing popular comic films and decides to hit the road to see the real men and women of depressed, unemployed, often indigent America, “Sullivan’s Travels” has a loose, slightly ramshackle structure and is not at all as tightly plotted as the classical Hollywood archetype. But somehow that adds to its charm, allowing it to retain a freshness to this day and walking a clever line between sympathizing with Sullivan and laughing at him. Of course, his Damascene conversion to the belief that comedies are worthwhile precisely because they give ordinary people a way to escape the misery of their lives is itself pretty reactionary and a little self-satisfied from Sturges, but who can complain when the gags are this quippy and Veronica Lake is this gorgeous?

“Swimming With Sharks” (1994) 
Giving a tremendous showcase to Kevin Spacey just before he really broke out (he’d win an Oscar for “The Usual Suspects” the following year), “Swimming With Sharks” compensates in sheer venom what it lacks in ambition. Written and directed by Robert Rodriguez pal George Huang, the film sees fresh-faced, wide-eyed writer Guy (Frank Whaley) starting to work for big shot movie mogul Buddy Ackerman (Spacey), only to swiftly discover that he’s a nightmarish, abusive bully, leading Guy to kidnap him and hold him hostage. Rumors persisted that Buddy was based on Scott Rudin or Joel Silver — +either way, Spacey’s mighty performance is near-definitive as far as movie bosses go, capturing both the insane demands and entitlement and the, ahem, people skills that lets his ilk get their way. It’s a performance so huge that it arguably overwhelms the rest of the movie, which is problematic given there isn’t much meat on the bones to begin with. In fact, it proved to work rather better as a stage play (Christian Slater and Matt Smith starred in the premiere in 2007), where its claustrophobia could really take off and its Mamet-ian language and nihilism had more room to flourish. 

“Tropic Thunder” (2008) 
Lord knows it’s hard to make a big, starry studio comedy that’s actually funny, and it’s harder still to do it when you’re doing it about the movie business itself, a subject that audiences reject more than they embrace. So Ben Stiller (and co-writers Justin Theroux and Etan Cohen) deserves a lot of credit for doing one that comes so close to greatness, though frustratingly falling short, as “Tropic Thunder.” Essentially a riff on “The Three Amigos” and “Galaxy Quest,” the film sees struggling action star Tugg Speedman (Stiller), committed method actor Kirk Lazarus (Robert Downey Jr.), fat-suit-loving comedian Jeff Portnoy (Jack Black), newbie Jay Baruchel and gay rapper Brandon T. Jackson forced to fight for their lives when the Vietnam movie they’re shooting puts them in the path of a heroin gang. Stuffed with cameos (including, most famously, an unrecognizable Tom Cruise as a monstrous studio executive), it stays somewhat disciplined in its scripting and manages a blend of big broad humor and a sense of something at stake, at least until its grip on reality slips in the third act. And almost every one of its expansive cast is well-served, with Downey Jr. in particular killing it with a layered, risky performance that somehow comes off (and ironically earned him an Oscar nomination). 

“Mulholland Drive” (2001) 
“Mullholland Drive” contains multitudes. It’s a delve into David Lynch’s mind. It’s a dreamlike fantasia. It’s a deceptively moving story of romance and broken hearts. It’s fucking terrifying. And it’s also one of the best movies ever made about Hollywood. “At night, you ride on the top of the world… You feel the history of Hollywood in that road,” Lynch said about the street of the title, a sort of boulevard of broken dreams, and the places he shoots and sets his movie in are just as important as the characters who populate it. First and foremost is Betty (Naomi Watts) an aspiring actress who falls for an amnesiac woman (Laura Harring). Perhaps kicking against expectations, Betty isn’t a has-been: she’s incredibly talented (as we learn in the incredible audition scene, one of the best bits of screen acting of this century and as authentic a look at that side of the process as has ever been portrayed), but is struggling to grab a foothold in an industry full of women that look just like her and is designed to chew up and spit her out. Indeed, later we meet Diane (Watts), the bitter, possibly murderous, definitely suicidal flipside of her doppelganger’s naive optimism. Both utterly nostalgic about the movies and the place that makes them and horrified by its dark underbelly, it’s a Hollywood yarn that only Lynch could have made. 

“S.O.B” (1981)
“It’ll become the greatest money-making film in motion picture history!” promises wild-eyed director Felix Farmer (Richard Mulligan) raving about his latest film. “… a 40 million-dollar box office champion!” It’s not only the numbers that have dated badly in Blake Edwards’ “S.O.B.,” a satire so broad and garish that it plays like farce. This film feels moored not just to an outmoded idea of Hollywood, in which one wealthy, successful director’s career dip is a thing worth caring about, but to an archaic view of American society in general, in which an extended sequence where a bunch of guys persuade, cajole and eventually drug an actress (Julie Andrews) into baring her breasts can be played for yucks. Oddly enough, “S.O.B.” is worth watching, if only because it may be the best example of unchecked, self-justifying vitriol ever to have assembled a slightly shop-soiled cast of film and TV stars (William Holden, Shelley Winters, Robert Vaughn, Robert Loggia, Larry Hagman and Loretta Swit) and to receive a greenlight. Based on his own experiences delivering flop “Darling Lili,” right down to casting his own wife Andrews, “S.O.B.” is shrill and largely unfunny, but fascinating for the feeling of Edwards trying to cover his gall with a grin. Without the ironic detachment of, say, “The Player,” the wacky failed suicides and corpse robbery incidents fall flat: he can’t mask his genuine pique, and the grin turns into a grimace. 

“The Artist” (2011) 
The baggage that follows a movie after it wins the Best Picture Oscar against competition more beloved by the critical community is often unfortunate: a product of our binary, fresh/rotten culture can be that if a film takes the top prize that isn’t the cinephile’s choice for best movie of the year, it’s immediately derided as the worst. But do you know what? “Chicago” is a pretty good movie. “Slumdog Millionaire” and “Argo” and “Birdman” are pretty good movies (this doesn’t cover all bases, as “Crash” proved, but still). And “The Artist?” When separated from the arbitrary awards process, “The Artist” is a pretty good movie, a modest, mostly delightful tribute to silent cinema that has nevertheless suffered the same backlash. Assembled in gorgeous black-and-white to a wonderful score by Ludovic Bource, Michel Hazavanicius’ film is more straight-faced than his previous collaborations with star Jean Dujardin on spy spoof series “OSS-17,” influenced as much by “A Star Is Born”-ish melodrama as by “Singin’ In The Rain” satire. But the surprise is that this mix of clowning and heartstring-tugging works, partly because it resists winking at the camera, and partly because it’s so steeped in the cinematic classics and is performed with such commitment by leads Dujardin and Berenice Bejo. It’s pastiche and it’s patently not the best film of 2011. But it’s still a pretty good movie. 

“Bowfinger” (1999)
Few comics have had the Hollywood success of Steve Martin or Eddie Murphy, so it’s perhaps appropriate that their first team-up and one of the finest hours from either came when they gently nibbled the hand that fed them. “Bowfinger,” written by Martin and directed by his “Dirty Rotten Scoundrels” helmer Frank Oz, sees the silver-haired star play an inept, Ed Wood-style filmmaker who sells a movie to a major studio (represented by a pre-comeback Robert Downey Jr.) on the condition that he must land megastar Kit Ramsey (Murphy). But when Ramsey disappears, he’s forced into less conventional methods, including the use of nerdy doppleganger Jiff (also Murphy). It’s loose, sometimes scrappily plotted, close in tone to something like “The Producers,” but it’s almost always winning: Martin’s script is consistently funny yet never overly sour about Hollywood, with a pleasing let’s-put-on-a-show feel to the capers that a great many Hollywood satires are lacking. It’s also notable as the last great big-screen live-action showcases for its two stars to date: Martin plays to his strengths as the dim-witted title character, while Murphy has rarely been more engaged and game as he pokes fun at himself as Kit, or more endearing and charming than he is as Jiff.

“The Last Tycoon” (1976)
When certain filmmakers turn their eyes inward to the industry that fosters and often breaks them, they often find the best response in humor, whether through biting satire or all-out farce. So it’s surprising that Elia Kazan, ever the most astute and provocative of directors, plays his Hollywood portrait as tragedy. But if “The Last Tycoon” never fully earns the operatic scope of its ambitions (except in the production design, which is exquisite), it hardly deserves its posthumous reputation as an all-out failure. In fact, in moments like the ping pong match between drunken mogul Robert De Niro and mustachioed union leader Jack Nicholson (still their only appearance together), it brushes against the greatness it seeks. Perhaps overreach was inevitable with a pedigree like this: Kazan directs De Niro at his early peak (this film came out the same year as “Taxi Driver”) in a Harold Pinter-scripted adaptation of F. Scott Fitzgerald‘s unfinished novel, which was itself based on superproducer Irving Thalberg, who dominated MGM until his untimely death at 37. But the cast is star-studded, including Theresa Russell, Jeanne Moreau, Tony Curtis, Robert Mitchum, Donald Pleasance and Ray Milland; the story is knotty with hubris, folly and eternally unfinished beach houses; and De Niro is hugely compelling in one of his most internalized roles.

“Somewhere” (2010)
Sofia Coppola‘s fourth feature film is really more of a mood piece/short film stretched out to a languid 98 minutes. But while it may not be her most vital or engaging work as a result, that deliberate pacing and detached, opaque approach imbues a perspective on Hollywood life that is valuable for being rarely seen. Film star Johnny Marco (Stephen Dorff) is not unsuccessful, nor is he “chewed up by the Hollywood machine” or any such cliché. In fact, Johnny has the kind of lifestyle that wannabe movie stars might see as aspirational —living at the Chateau Marmont, traveling to Italy for TV appearances, ordering sex as casually as ordering dinner— and yet he remains unfulfilled. The vacuity of his existence is undoubtedly immensely #firstworldproblems, and that poor-little-rich-guy vibe contributes to some desperately low stakes, only partially enlivened by the arrival of his daughter (a terrific Elle Fanning) and the gradual dawning of a sort of self awareness. But in its own way, this somnolent, straight-faced story is as honest an insight as Coppola, a scion of Hollywood royalty, can make about her rarefied milieu, and there is some compassion in her suggestion that the grass may be greener over this side of the fence, but that just means you live out your discontent in more verdant surroundings. It’s far too slight an observation to hang a whole film on, let alone one as serious as this one, but it is at least sincere. 

“Barton Fink” (1991)
“Hail Caesar!” is not the first time the Coens have delved into the Hollywood history files for inspiration: this Cannes-winning 1991 film is set in 1941 and follows delusional playwright Barton (a career-defining John Turturro) as he becomes a Hollywood screenwriter while attempting to hold on to the creative integrity he erroneously believes he possesses. The picture of classic Hollywood the brothers paint here is larger-than life  —especially as embodied by studio head Jack Lipnick (an Oscar-nominated Michael Lerner)— but also nuanced. Sure, the industry is all bluster and phoniness, and sure, Lipnick will try to dress up a Wallace Beery wrestling picture as an art film if it will get Barton to fall into line. But the phoniness is made plain up front —it’s weirdly honest, especially contrasted with Barton’s own dangerously oblivious, condescending variety. After all, Hollywood knows where Barton fits, but he misunderstands the significance of his own life. He is not the noble hero living “the life of the mind”; Charlie (John Goodman) is not his goodhearted, dim-witted sidekick; JP Mayhew (John Mahoney) is not his inspirational mentor and Audrey (Judy Davis) is not his paramour. “Barton Fink” is great at many things: it’s one of the greatest hotel films, one of the greatest films about the writing process, and one of the greatest films about self-delusion and steep learning curves. Almost by-the-by, it’s also one of the greatest ever films about Hollywood. 

“The Day of the Locust” (1975)
As blackhearted as many Hollywood takedowns may be, perhaps none stray quite so deep into all-out expressionist Gothic nightmare as John Schlesinger‘s film adaptation of Nathanael West‘s celebrated 1939 novel. It’s less a linear story than a temporally hazy jumble of fragments collected around a perverse love triangle involving newbie art director Tod (William Atherton), a manipulative, aspiring actress who lives on his block (Karen Black) and a sexually repressed accountant who’s naive in the ways of Hollywood (Donald Sutherland). That Sutherland’s character is called Homer Simpson is just one further bizarre and slightly distracting facet of a film that is already hard to gain any sort of emotional purchase on. However, some of its jarring, semi-surrealist imagery is remarkable for its evocation of Hollywood Grotesque: the creepy wannabe child star sing-songs maliciously and apes a sexualized Mae West; the actress’ drunkard ex-vaudevillian father goes door-to-door doing lame magic tricks to sell suntan lotion; the actress herself primps and preens and teases while sliding inevitably into prostitution. But for blunt, nasty moralism, nothing beats the moment when one character kicks a child to death in front of a crowd assembled for a De Mille premiere before the mob turns on him and rips him apart. Subtle it is not, but this often confounding film evokes as well as any the grimy desperation of the many who don’t ever bask in the limelight, instead spending their lives clawing fruitlessly for the chance.

“A Star is Born” (1954) plus “What Price Hollywood” (1932), “A Star is Born” (1937), “A Star is Born” (1976)
We’re long overdue another iteration of this now familiar story: a young ingenue is taken under the wing of an older, substance-abusing movie star. But as her career takes off, his goes into decline, which puts strain on their romantic relationship and eventually leads to his suicide. It’s the classic bargain-with-the-devil narrative transposed to Hollywood, and the fact that it had its first incarnation back in 1932 shows just how long Hollywood has considered itself both the maker and the breaker of dreams. George Cukor directed both “What Price Hollywood” (which is a little different, in that the older mentor figure is a director rather than an actor) and also the still-definitive 1954 version with a career comeback Judy Garland and James Mason in the lead roles. It’s a grand slice of Hollywood melodrama, beautifully played and mounted, although William Wellman‘s 1937 iteration is also excellent if slightly less glossy and grand, with Fredric March and Janet Gaynor in the lead roles. The last version is also probably the least —Frank Pierson‘s 1976 film stars Barbra Streisand and Kris Kristofferson and feels a lot like the star vehicle for its leading lady that it reportedly was, but it was also a massive hit, and if the “A Star is Born” narrative has taught us anything through the decades, it’s that Hollywood doesn’t really care about anything but success. 

“State and Main” (2000)
Caustic and hilarious but strangely affectionate too, David Mamet‘s terrific, bafflingly underseen “State and Main” (no way this film’s take should be sub-$10m worldwide) is an immensely enjoyable evisceration of the failings of the system, that manages to avoid the all-out mean-spirited cynicism of other Hollywood satires. Maybe it’s because of Mamet’s clever-clever, not-strictly-naturalistic dialogue, or maybe it’s because the game cast are so good at delivering that dialogue with relish and warmth, but “State and Main” is the rare satire that has teeth but actually feels like it likes its characters too. Well, some of them: Philip Seymour Hoffman‘s blocked screenwriter is, perhaps unsurprisingly, given a sympathetic showing, and his potential redeemer — oddball local bookshop owner Rebecca Pidgeon — is charmingly off-kilter too. But even William H Macy‘s director character and the egomaniacal stars Alec Baldwin and Sarah Jessica Parker feel more than just ciphers, no matter how petulant and petty their behavior. Perhaps that’s all because, in this frequently laugh-out-loud funny send-up of Big Hollywood descending on a small town, there is still a tiny bit of room left, after all the drama and cross-purposes and maneuvering, for an admission that it might actually all have been worth it. Oh, and Alec Baldwin stepping away from a car he’s just crashed and saying “So that happened” is one of the greatest things ever.

“The Big Picture” (1989)
Christopher Guest‘s feature directorial debut, starring a perfectly on-point Kevin Bacon as the award-winning film student all too eager to allow Hollywood to corrupt his youthful idealism, might be slight, insubstantial and overly inside-baseball, but it’s stuffed with little pleasures. The myriad cameos, often unbilled, are a device that works here better than in Guest’s later films when we became accustomed to expecting them. Overall there is a freshness to the ensemble spoof/comedy that his more recent outings have lacked. Additionally, JT Walsh and Jennifer Jason Leigh turn in strong performances as a movie exec and a kooky long-suffering friend respectively, and while Martin Short‘s smarmy agent and Teri Hatcher’s scheming starlet might be stereotypes, the actors chew into them with relish. The film feels like fairly gentle satire now, as much suggesting that Bacon’s Nick is a victim of his own hubris and ego as he is preyed on by an uncaring, creatively and morally bankrupt Hollywood machine (though, you know, that too) But at the time it reportedly made Columbia execs, piqued at what they saw as a negative portrayal, nervous enough to bury the film in a small release before whooshing it to home video, resulting in it recording a fairly hefty loss. It’s an ironically perfect coda for a film satirizing the movie business in which the director suffers when a studio head is ousted, considering David Puttnam, who greenlit the movie, was removed as Columbia chairman just two weeks after production began.

“Hollywoodland” (2006)
The biggest critique of Allen Coulter‘s “Hollywoodland,” the other film apart from “Hail Caesar!” to feature studio fixer Eddie Mannix (here played by Bob Hoskins) in a key role, is unavoidable for this sort of true mystery hypothesis: the theory, or theories it puts forward as the possible solutions to the conundrum of TV Superman George Reeves‘ (Ben Affleck) mysterious death can never be proven true or false, so it’s destined to be at least a little unsatisfying. Additionally, Coulter and writer Paul Bernbaum try to shape the story into a kind of noir mystery, by adding in a fictional gumshoe, Adrien Brody‘s Louis Simo, who duly gets “obsessed by the case” and “will stop at nothing to find the truth.” Such well-worn generic conceits somewhat undersell the true story on which it’s based, and it’s a shame because other elements are strong. Diane Lane‘s performance as Mannix’s tigerish wife, who did indeed have an affair with Reeves and who was widely believed to have been kept clean of the ensuing scandal thanks to the machinations of her powerful husband, is keen-edged and clever, and Hoskins makes a charismatic and ambivalent Mannix. But really Affleck is the standout, in a self-reflexive turn as the doomed Reeves, a tragic figure trapped by the persona that brought him recognition but no respect. Poor George Reeves may not have ever got another decent role, but he did eventually become one.

“LA Confidential” (1997)
If ever a novel should have been deemed “unfilmable”, James Ellroy‘s “LA Confidential,” a sprawling story couched in his trademark crisp, staccato prose, should probably have been it. But screenwriter Brian Helgeland and director Curtis Hanson took exactly the right approach, which was to interpret the book rather than adapt it, and the result is simply one of the greatest films of the last twenty years, and one of the most impressive, atmospheric and evocative films noir ever made. Less involved with the Hollywood of big movie studios and major stars (Lana Turner’s brief appearance aside) the film takes places among the next-tier down scrabblers, TV actors and hookers “cut to look like movie stars.” And it’s a gloriously seedy panoply of 1950s Los Angeles characters and issues — from police corruption and the mob, to prostitution rings and sting operations co-sponsored by gossip rags. It’s less a portrayal of Hollywood than a suggestion of how the Hollywood myth is so shiny and seductive that it corrupts everything it touches, and that nestling in the shadow of its iconic sign is a cesspool of venality. Featuring Russell Crowe‘s breakout performance, alongside Kim Basinger‘s best-ever turn and Guy Pearce, Kevin Spacey and James Cromwell all being typically brilliant, “L.A. Confidential” is maybe most impressive for embodying exactly the paradox of the Hollywood it critiques. It’s a cynical cautionary tale about the moral degradation and famewhorishness of 1950s LA that is simultaneously so grimily glamorous that it somehow makes you wish you lived there.

As mentioned, there are many hundreds of movies about Hollywood, so don’t kvetch if your favorite isn’t represented above. Or do, but do it in the comments. In the meantime, here’s a brief selection of suggested titles for further reading — a few of our favorites that didn’t make the cut this time: “Get Shorty,” “Inserts,” “The Carpetbaggers,” “Paris when it Sizzles,” “For Your Consideration,” “In a Lonely Place,” “Who Framed Roger Rabbit,” “The Bad and the Beautiful,” “Whatever Happened to Baby Jane,” “Sherlock jr,” and “The Purple Rose of Cairo.” 

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