City of Angels sets its mood immediately, with a Robin Wagner set (half architecture, half movie poster) that extends into the theater, and a musical Prologue: Theme From City of Angels that incorporates orchestra, scat vocals, and a suitably world-weary voice-over by Stone that plunges us into the realm of 1940s detective movies.
As the curtain rises, Stone lies on a hospital gurney with a bullet in his shoulder and a lot on his mind. A tough private eye in the tradition of Philip Marlowe and Sam Spade, Stone also suffers from a bruised heart (owing to a weakness for beautiful women) and an empty wallet(he's too moral to take dishonest jobs).
Stone flashes back to a week earlier, when his secretary-with-a-heart-of-gold, Oolie, ushered in a rich, beautiful woman named Alaura. Alaura claims she wants Stone to find her missing stepdaughter; against his better judgment he takes the case. And just as we're becoming intrigued...
A man at a typewriter appears on stage, and the actors are suddenly backing up, "rewinding," and playing the scene with a few changes. The man, we discover, is Stine, author of popular detective novels starring Stone, on of which he is now adapting for his first screenplay. What we've seen comes straight from his imagination.
Like Stone, Stine has a weakness for women, but fewer scruples when it comes to money. At the moment, the money is coming from Buddy Fidler, Hollywood mogul and master puppeteer of creative people. Something's telling Stine to watch out, but for now, he's just enjoying the ride (Double Talk).
Back at Stine's hotel room, we learn that the misgivings come mostly from his wife, Gabby, who wishes Stine would stick to novels. He won't listen, though, any more than Stone will, and we begin to see the interplay between "reality" and fiction as Gabby and Oolie lament What You Don't Know About Women.
The Mystery resumes, with Stone, alone in his dreary bungalow, listening to crooner Jimmy Powers and the Angel City 4 brightly telling their radio audience, You Gotta Look Out For Yourself - which takes on a certain poignance when two hoods break down his door and beat him up.
Cut to Buddy reading this scene in the screenplay: we see that his secretary, Donna, is the model for Oolie, and that Buddy can't help "fiddling" with everything (The Buddy System).
And Back to Stone, out cold, being rudely awakened by LAPD Lt. Munoz, who was Stone's partner on the force but now bears him a major grudge. Stone, it seems, loved a low-rent lounge singer named Bobbi (Stine has based her on Gabby), whom we see performing a torchy ballad (With Every Breath I Take). But Bobbi wanted stardom more than marriage, and when Stone caught her with a Hollywood producer (based of course on Buddy), tempers flared, a gun went off, and the producer was dead of a "heart attack" caused by two bullets. Munoz has never forgiven Stone for "getting away" with the murder, and would gladly nail him for jaywalking.
Stone, Angry about the beating, confronts Alaura at her mansion and meets several more unsavory characters, including her lustful stepson, her war-profiteer husband (an elderly man stricken with polio and encased in an iron lung), and the quack spiritualist who attends him. Greed and malice hover like smog, but Alaura's considerable charms (and bankroll) keep Stone on the case(The Tennis Song).
Stone fruitlessly pursues the "missing" stepdaughter, Mallory (the scatted Ev'rybody's Gotta Be Somewhere), in a scene that recalls a film montage, only to find her waiting naked in his bed (the provocative Lost And Found). Stone somehow manages to resist temptation....
Which is more than can be said for his creator. His wife having returned to New York, Stine takes comfort in Donna's bed, although not without some guilt. but this is Hollywood, after all, where no one's motives are pure...
As Stone quickly learns, when a photographer breaks in, snaps him with Mallory, and she runs off with his gun, which is used to murder the quack. Stone finds himself framed for the killing and gleefully arrested by Munoz (the sardonic All You Have To Do Is Wait).
Not that Stine is having such a great time, either. Buddy is butchering his script, his conscience is nagging, and Stone, his own creation, is disgusted with him. The curtain falls with each of them arguing, to a swingin big-band accompaniment, You're Nothing Without Me.
Act II opens in a recording studio, where Jimmy Powers and the Angel City 4 are waxing Stay With Me, which then becomes a record playing in...whose bedroom? It looks like Alaura's, but proves to belong to Carla Haywood, Buddy's wife, who'll play Alaura in the movie.
Stone, meanwhile, languishes in jail, attended only by Oolie, who like her alter ego, Donna, is feeling used by men (the brassy You Can Always Count On Me). Stone is mysteriously bailed out, but the two hoods catch up with him and nearly blow him up before he neatly turns the tables.
Stine has troubles of his own. Lonely at a lavish Hollywood party of Buddy's sycophants, including a typical Hollywood composer (the lush Alaura's Theme), Stine calls home only to find that Gabby has discovered his affair with Donna. He flies to New York with an elaborately prepared excuse, but she's not buying it (It Needs Work).
Stone, fighting now to clear his name, is led to a brothel (LA Blues) where he is stunned to find Bobbi. We learn it was she who shot the producer; Stone has been covering for her all this time. Together they face the wreckage of their love (With Every Breath I Take).
Oolie, meanwhile, has made her own discovery: Alaura is a fortune hunter who has already murdered one rich husband and planned to do away with this one, once she had eliminated his son, daughter, and doctor. Stone confronts her at the mansion; they grapple for her gun; shots ring out...and Alaura falls dead, Stone's gravely wounded, and we're back where we started.
But where does that leave Stine? His wife has rejected him, his lover, Donna, has (he learns) also been rewriting his script; Stine faces the collapse of his real and fictive worlds, and as his emotions take over, his wit turns bitter (Funny).
When he arrives on the movie set to find that Buddy's name appears above his on the screenplay, and that the shallow crooner Jimmy Powers will play Stone, Stine boils over. With the "real" Stone, his conscience, finally leading him to make the right choice, he rages at Buddy, gets himself fired, and is about to be pounded by two security guards when - in the imagination all things are possible - Stone somehow appears at Stine's typewriter and writes him the fighting skills of a superhero, then tacks on a "Hollywood ending" in which Gabby returns, forgiving all. Together they celebrate (I'm Nothing Without You) as the curtain falls.
The Evening doesn't end there: we leave as we entered, with the band swingin (Epilogue: Theme From City of Angels and Double Talk Walk) to an emphatic coda. The great 52nd Street jazz clubs are history, but like no show before it, City Of Angels deserves to play on "Swing Street."
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