Act One

You're in prohibition-era New York City, just before the crash in 1929, a time of flappers, jazz, bathtub gin and pistol-packing gangsters. The curtain is a mural of dancing chorus girls and musicians playing trombones and saxophones. The orchestra plays the "Overture" and Cheech, a machine gun-toting hit man in the service of boss, Nick Valenti, casually walks out and fires at the curtain, spelling out "Bullets over Broadway." At Nick's club, a speakeasy in midtown Manhattan, akin to the real Three Deuces or "21 Club" on 52nd Street, the gorgeous Atta-Girls are in full swing with "Tiger Rag." Among them is Olive Neal, Nick's burlesque dancer girlfriend who yearns for the big part in a Broadway show that he has guaranteed her ("I promise I'll have your name in lights,") but not yet delivered. ("The only way you'll ever have my name in lights is if I change my name to Exit.") But, "Gee Baby, Ain't I Good toYou?"

David Shayne, a playwright and self-proclaimed "serious artist," sings the same lyrics to his long-suffering girlfriend of ten years, Ellen. His new play has been turned down by every producer in New York except for Julian Marx, who calls to say that he has a single backer – Valenti; all David has to do is find a part for Olive. Ellen asks that, if the play is not a success, they will move back to Pittsburgh, get married and have a "real life." "I hear you," David assures her, "but you have to realize that marriage is a very serious decision – like suicide." Ellen laments the "Blues My Naughty Sweetie Gives to Me."

"'Tain't a Fit Night out for Man or Beast" as a pack of Valenti gangsters shoot it out with members of the rival Kustabecks. David and Julian go to Nick's house to meet about the play, and Olive demonstrates her singular ability in "The Hot Dog Song." Julian visits the aging diva, Helen Sinclair, to persuade her to take the lead. "You want me to play a frumpy housewife who gets dumped for a flapper?" she answers in disbelief. "I'm Helen Sinclair!" ("They Go Wild, Simply Wild, over Me").

Cheech, singing "Up a Lazy River" as he drives a mug to Gowanus Canal, shoots him on Valenti's orders. David enters the theatre for the first day of rehearsals, thrilled: "I'm Sitting on Top of The World." Olive's flawlessly untalented reading turns the song into a dirge. Cheech is a fount of suggestions for improving the script.

Olive catches the eye of male lead, Warner Purcell, who suggests "Let's Misbehave." David falls for Helen, who cagily uses his infatuation to improve her part. On his birthday, she gives him a silver cigarette case that she received from Cole Porter, inscribed "Let's Do It," and explains "There's a Broken Heart for Every Light on Broadway." David joins Ellen at Nick's club, where the Atta-Girls are singing "(We'll Be Glad When You're Dead) You Rascal You" while "Here Comes the Hot Tamale Man" plays. During a break in rehearsal a few days later, David has misgivings about passing off Cheech's now voluminous changes as his own. "What are you worried about, I ain't going to tell anybody," he says. "'Tain't Nobody's Business If I Do." Act 1 ends with the cast aboard the train for Boston Tryouts as the leggy Red Caps sing "Runnin' Wild."

Act Two

The cast is overjoyed ("There's a New Day Comin'!") by the daily improvement of what they don't know is Cheech's script. Cheech, assigned by Nick to be Olive's bodyguard, confronts Warner about his involvement with her and tells him "There'll Be Some Changes Made." Helen, impressed by "David's" rewrites, intimates that she's available but "I Ain't Gonna Play No Second Fiddle." David tells Ellen that he has fallen for Helen, and her answer is "I've Found a New Baby." Hours before opening night on Broadway, Olive's body is found in the Gowanus Canal, shot by Cheech for ruining "his" show. David is horrified. "The Panic Is On."

The show is a hit. David realizes that Cheech was the real artist and reconciles with Ellen in "She's Funny That Way," while the cast looks on the bright side: "Finale (Yes, We Have No Bananas)."