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At the turn of the century, entertainers Trudy Evans, Johnny Cornell, Dan Daley and Beulah Clancy struggle to become successful in the Barbary Coast section of San Francisco.  Trudy is the star singer of the act and is in love with Johnny, who also acts as the group's manager.  Despite his humble origins, Johnny has aspirations for a better life on Nob Hill, the high society part of town.

After the quartet is fired from Sharkey's Coliseum for distracting the customers from drinking, Johnny concocts a scheme of singing in the streets and extorting money from saloon owners who want them to go away.  Dan and Beulah are skeptical of Johnny's ambitions but stay in the group for Trudy's sake.

Soon Johnny's idea pays off and with the money he opens his own club, The Grizzly Bear, and features Trudy as the main attraction.  Despite the success of The Grizzly Bear, and other clubs he soon opens, Johnny still dreams of entering society and becomes involved with snobbish socialite Bernice Croft.  Trudy, meanwhile, longs for Johnny, although it is obvious that he thinks of her as a singer first and a woman second.

When Bernice loses her fortune due to bad investments, Johnny buys most of her possessions at an auction.  Dan warns him about becoming involved with Bernice, but Johnny brushes him aside and offers to buy Bernice's house.  Seeing a way out of her predicament, Bernice cajoles Johnny into proposing to her so that she will be able to maintain her standard of living.  Trudy is devastated and accepts the offer of impresario Douglas Dawson to star in his new London show.

While Trudy is a success abroad, Johnny re-opens the opera house founded by Bernice's late father.  As Johnny spends his money on the opera house and Bernice's flighty friends, his Barbary Coast clubs go out of business until only The Grizzly Bear remains.  Dan urges Johnny to ask Trudy to return, but Johnny stubbornly refuses and, soon after, Dan and Beulah are again working at Sharkey's after The Grizzly Bear closes.

Johnny is forced to close the opera house as well and, during an argument, Bernice coldly informs him that she married him only for his money.  Johnny gives her the deed to the house and after obtaining a divorce, works as a barker for a sideshow.  Trudy, who has returned to San Francisco for a new show, is told about Johnny's troubles by Dan and Beulah.  Trudy then concocts a ruse whereby Sam Weaver, a prospector whom Johnny has staked for years, pretends to have struck it rich and repays Johnny.  Johnny is able to re-open The Grizzly Bear with the money, although on opening night, a drunken Sam reveals its true source.  Johnny's pride overwhelms him and he is about to close the show when Dan tricks him into singing onstage with Trudy.  While performing with Trudy, Johnny finally realizes that he loves her, and they embrace as Trudy performs her signature song, "You'll Never Know."