1. Neely O’Hara (“Valley of the Dolls”)
Before Lindsay Lohan, there was Neely O’Hara (Patty Duke). One of Valley of the Dolls’s three tragic leading ladies, Neely got hooked on dolls (prescription pills) and booze. Worse, she became a real pain in the ass to work with. Neely was based on Judy Garland, who had a part in the film but was eventually fired.
2. Les Grossman (“Tropic Thunder”)
Tom Cruise was nearly unrecognizable in Tropic Thunder, but those in the entertainment industry likely recognized the character. Whether or not Les Grossman has a real-life inspiration, there are plenty of overbearing Hollywood producers who think they’re a lot hipper than they really are.
3. Guido Anselmi (“8 1/2”)
Poor Guido (Marcello Mastroianni) has director’s block — hey, it’s a thing — and a very complicated love life. (The latter’s not always such a bad thing.) Throughout 8 1/2, he gets lost in his memories and fantasies as he struggles to complete his current project, a science fiction film.
4. Sandy Bates (“Stardust Memories”)
Clearly an homage to Guido, Woody Allen’s director character Sandy Bates has to deal with fans who prefer his “earlier, funnier movies” — kind of like Woody Allen. Stardust Memories was shot in black-and-white as a parody of 8 1/2. Sandy’s fans would almost definitely hate it.
5. Elise Elliot (“The First Wives Club”)
Elise (Goldie Hawn) isn’t shallow: she’s just misunderstood. Probably because she’s plumped her lips up with so much collagen she can barely speak. Luckily, she’s eventually able to mellow out and get sober. She even lands a role in a Broadway play, the perfect comeback for the film star.
6. Norma Desmond (“Sunset Boulevard”)
While we’re on the subject of faded leading ladies, who could forget Sunset Boulevard’s Norma Desmond? Modeled after Norma Talmadge and played by Gloria Swanson, Desmond was a fallen screen idol dreaming of her comeback. Spoiler alert: never gonna happen.
7. Cecil B. Demented (“Cecil B. Demented”)
Norma Desmond had her Cecil B. DeMille, but John Waters gave us Cecil B. Demented (Stephen Dorff). A “kamikaze filmmaker,” he’s willing to kidnap an A-list star for his art. He’s also willing to die for it — not to mention get some of his associates killed.
8. Johnny Marco (“Somewhere”)
Stephen Dorff also played Johnny Marco in Somewhere, Sofia Coppola’s subtle drama about a famous actor reconnecting with his 11-year-old daughter. With so many troubled actresses on this list, shouldn’t there be a struggling, boozy actor represented? Thanks for being such a screw-up, Johnny.
Dana Marschz (“Hamlet 2”)
From failed actor to high school drama teacher, Dana Marschz’s story is a sad one. Steve Coogan plays human flop Dana in Hamlet 2, a hilarious satire that never really got its due. Neither did Dana, whose biggest credits were an episode of Xena and a herpes commercial.
9. Vicki Lester (“A Star Is Born”)
Of course, success isn’t always a good thing. Just ask Vicki Lester (Judy Garland). In the first remake of A Star Is Born, Vicki does her best to maintain her career while taking care of her mess of a husband, alcoholic actor Norman Maine. In real life, Garland had plenty substance abuse problems of her own.
Baby Jane (“What Ever Happened to Baby Jane?”)
Being a child star is hard! Bette Davis gives it a particularly demented spin in camp classic What Ever Happened to Baby Jane? With caked-on makeup, Jane goes full-on murderess as a result of her dark past and twisted obsession with fame. She’s also not a great sister to Blanche (Joan Crawford).
10. Buddy Ackerman (“Swimming With Sharks”)
As far as terrible bosses go, few are worse than Buddy Ackerman (Kevin Spacey). Buddy is a tyrannical, abusive movie mogul, but that’s just because he’s trying to teach his naive assistant how to make it in the business. Some say Buddy was inspired by Scott Rudin — which is, of course, just speculation.
11. Carl Denham (“King Kong”)
Another not-so-great boss: Carl Denham (Robert Armstrong). Hell, he just wanted to make a great picture, but he put his cast and crew in considerable danger in the process. He’s also sort of responsible for the whole King Kong rampage. In Peter Jackson’s remake, Jack Black steps into Carl’s shoes.
12. Marilyn Hack (“For Your Consideration”)
Poor Marilyn Hack (Catherine O’Hara) finally found her comeback in Home for Purim. There was even talk of an Oscar nomination! But as Christopher Guest’s For Your Consideration reminds us, it’s all too easy to get caught up in the buzz. Marilyn ends up with horrible plastic surgery and no Oscar nod.
Charlie and Donald Kaufman (“Adaptation”)
Twin-brother screenwriters, both played by Nicolas Cage, Charlie and Donald Kaufman battle for success in Spike Jonze’s trippy Adaptation, loosely inspired by the real Charlie Kaufman’s attempts to adapt Susan Orlean’s book The Orchid Thief. The film takes several dark turns before The Orchid Thief screenplay gets finished.