This 1994 film is one of Creator/WoodyAllen's dramedies on the creative process.
[[TheRoaringTwenties In the 1920s]], idealist playwright David Shayne (Creator/JohnCusack) moves to New York City to produce a play. He and his girlfriend Ellen (Mary-Louise Parker) fit in well enough in the show business world and David finds a mentor in Sheldon Flender (Rob Reiner), a bohemian artist who says that artists can get away with things normal people can't [[TrueArtIsIncomprehensible because artists live in their own moral universe]].
With the help of his associate Julian Marx, David gets a play produced even though his last two endeavors were flops. Unfortunately there's a catch: the play is backed by Nick Valenti, the head of a violent [[TheMafia Mafia gang]]. Despite worries that he's selling out, David agrees to direct the play according to Valenti's conditions. The main condition being that Valenti's girlfriend Olive (Creator/JenniferTilly, who earned an UsefulNotes/AcademyAward nomination for her performance) receive a starring role in the play despite her terrible acting skills. Olive's hostile bodyguard Cheech (Chazz Palminteri) is required to sit in on rehearsals and guarantee that everyone treats her right.
The rest of the cast is David's dream cast. He manages to persuade one-time legendary actress [[GrandeDame Helen Sinclair]] (Dianne Wiest in her second UsefulNotes/AcademyAward under Woody Allen) to play the lead role, but her overbearing personality and constant demand for script changes proves problematic. David also hires Warner Purcell (Jim Broadbent), an excellent performer with [[BigEater a serious eating addiction]].
But the biggest problem is with the play itself. It is pretentious and badly written, so much so that Cheech starts making suggestions on how to improve it. David begrudgingly takes Cheech's writing advice and ends up having to decide whether art or life is more important.
* AllPartOfTheShow: During the show's opening night on Broadway, [[spoiler: a pair of mobsters shoot and kill Cheech backstage. The audience thinks the gunshots were all part of the show. In fact, the show gets rave reviews because of the "symbolic" gunshots in the ending.]]
* AuthorExistenceFailure: InUniverse, ItMakesSenseInContext
* BadBadActing: Olive, and it's not an InformedAbility. We get to see how bad she is - '''HA!'''
* BerserkButton: Olive's bad acting [[spoiler: finally pushes Cheech over the edge.]]
* BigEater: Warner Purcell is a compulsive eater. Olive even invokes the trope verbatim.
-->'''Warner:''' Before we start...
-->''(Warner pulls a turkey leg out of his pocket and eats it)''
-->'''Olive:''' What? Oh. Just a... a little poultry. ''(giggles)''
* BittersweetEnding / DownerEnding: [[spoiler: David's play is a hit but all the best parts of it were written by the now dead Cheech. David discovers that he is not really an artist and plans to move back to Pittsburgh and marry Ellen.]]
* DamnedByFaintPraise: When David asks Helen if there was ANYTHING good about the script he wrote (before it was rewritten by Cheech in secret), Helen says that the stage directions were good and the color of the folder was appropriate.
* DoingItForTheArt: David and eventually Cheech as they write the play.
* EnforcedMethodActing: [[invoked]] Near the end.
* GenkiGirl: Eden Brent is a giggly flapper.
-->'''Helen:''' She's perky all right. She makes you want to sneak up behind her with a pillow and suffocate her.
* HiddenDepths: Cheech. A mob goon turns out to be a brilliant playwright.
-->'''Helen''': Two martinis, please, very dry.
-->'''David''': How'd you know what I drank?
-->'''Helen''': Oh, you want one too? Three.
* IronicEcho: "Don't speak. Don't speak. Don't speak." Doubles as a FreudWasRight.
** The first line of the film is David shouting, "'''I'm an ''ARTIST''!'''" The last line of the film is David admitting, "I'm not an artist."
* JerkAssHasAPoint: Olive is dense about most things, but she's right about David's stilted dialogue.
* LadyDrunk: Helen Sinclair.
* LargeHam: Helen, both on stage and in real life.
* TheMafia: The reason the play is produced, and the reason Olive can't be fired.
-->'''Julian:''' It's not the money. I told ya that. We dump Olive, you, me, [[AndYourLittleDogToo even the dog]] [[CementShoes will wind up at the bottom of the Hudson.]] It won't take that long. He'll kill us here in Boston. We'll be at the bottom of the Charles.
* MobWar: Nick Valenti is engaged in a turf war with Leo Kustabeck. We even see some of Valenti's mooks getting gunned down in a drive-by.
* MythologyGag: A dying Cheech tells David to have the Sylvia Poston character, played by Diane Wiest, reveal she's miraculously pregnant. That's basically how ''Film/HannahAndHerSisters'' ended, with Wiest's character making that revelation.
* PreMortemOneLiner: "[[spoiler: Olive]], I just want you to know one thing: you're a ''horrible'' actress."
** Doubles as a BrickJoke.
** Cheech's favorite spot to execute rival gang members. [[spoiler: Olive becomes the last one.]]
--->♪ ''Up a lazy river by the old mill run...'' ♫
** Warner Purcell keeps eating... and eating... and eating...
* SassyBlackWoman / ServileSnarker: Venus.
-->'''Venus:''' ''(to Olive)'' You better get in the mood, honey, 'cause he's payin' the rent.
* ShowWithinAShow: We get to see a lot of the play in various states of development.
* SoundtrackDissonance: Cheech's assassinations are accompanied by the 1930 standard "Up a Lazy River". [[spoiler: It's signals a BrickJoke when Cheeck is driving Olive to his "favorite spot".]]
* ThrowItIn: [[invoked]] Olive thinks you can do this in a play. She claims it's ad-libbing, but it's completely inappropriate.
** [[spoiler: Cheech's dying line, an IronicEcho of Helen's, "Don't speak", was ad-libbed by Chazz Palminteri]].
* TitleDrop: In a blink-and-you'll-miss-it moment, the character of Sylvia cries out "Oh, God of our fathers, save me!" The ShowWithinAShow's title is ''God of Our Fathers''.
* TrueArtIsAngsty / TrueArtIsIncomprehensible.[[invoked]] Flender firmly believes this ("My plays are written specifically to go unproduced!"). David initially believes this. Cheech thinks it's pure bullshit (and he turns out to be the best writer of them all.)
* WhiteDwarfStarlet: Helen, though [[HeReallyCanAct She Really Can Act]].
-->'''Helen:''' I never play frumps or virgins.
* WideEyedIdealist: David Shayne is painfully naive at times when it comes to producing a play.