It's a biopic of Hollywood starlet and heiress Diana Barrymore, based on her own memoir of the same title. The film opens in the late 1930s with Diana, a teenager, desperate to start a relationship with the father she barely knows, acting legend John Barrymore. Her mother Michael warns her that her father is an unreliable alcoholic wreck, but she goes out to California anyway. John, played by Errol Flynn, is in fact an unreliable alcoholic wreck. They get along together relatively well but John eventually hears the call of parties and the bottle and sends Diana back home.
A little time passes and Diana, born to wealth and with nothing else to do, goes to Hollywood again to give acting a shot. As it turns out she has little talent but gets a movie contract based on her name (both her father and her uncle Lionel Barrymore were huge stars). She connects with her father again, but John Barrymore soon dies of alcoholism. Grief-stricken and guilt-ridden over her father's death, Diana takes to the bottle herself, and follows her father's path.
In Real Life, Diana Barrymore died of alcohol and drug addiction in 1960 at the age of 38, less than two years after this movie was released. And Errol Flynn died barely a year later of a heart attack brought on by alcohol abuse.
- Absence Makes the Heart Go Yonder: One of Diana's problems is an extreme neediness that renders her incapable of being alone. When her first husband Vincent goes off to shoot a movie, she engages in an alcohol bender that leads to her cheating on him, and him dumping her when he gets home and catches her with another man.
- The Alcoholic:
- John Barrymore literally drinks himself to death. As he ruefully admits his valet is really his "keeper", but Barrymore still squirrels away alcohol in a suit of armor which is one of the few possessions he hasn't had to sell. When John goes to a press party for his daughter's film debut, the PR guy is petrified that he might touch the liquor at the food table.
- Diana becomes a stumbling drunk herself in turn. Her third husband is also The Alcoholic, who's managed to quit drinking for eight months, but she drags him down with her. Eventually she's institutionalized for drinking.
- Bikini Bar: A burlesque club in a 1950s movie, which means that the stripper onstage keeps her corset on and only throws a couple of tassels before her act is over.
- Biopic: Of Diana Barrymore, whose own life was even sadder than it's shown in this movie.
- Chekhov's Gun: John Barrymore points out an old suit of armor in his home that's one of the only things he has left, most everything else being sold to pay his debts. He laughs and says it's his "penny bank". Later it turns out that the suit of armor is where he hides his liquor.
- The Faceless: An interesting shot that comes when John Barrymore and Diana are out on his yacht. Another boat, full of partying drunks, pulls alongside. They all know John and they banter with him, getting him to spout some Shakespeare before they tempt him to come over and join them in drunken carousing. He thus abandons his daughter. Throughout the whole scene, the faces of the partygoers are never seen; they're framed in silhouette against the lights of the boat.
- Fallen-on-Hard-Times Job: Diana has fallen pretty far by the point where she is appearing in some sleazy burlesque club, doing awful impressions of Greta Garbo and Marilyn Monroe. She gets fired from that job when she comes out onstage drunk and starts stripping for the patrons.
- Gilligan Cut:
- Michael grudgingly agrees to let Diana write her father, hissing "Find out how much interest Jack Barrymore has in his daughter." Cut to Diana and John having a grand time as they go deep-sea fishing on his yacht. Later this is subverted when John clearly grows bored with Diana's teenaged chatter.
- A much darker example when Diana is talking with Robert Wilcox, her co-star in an off-Broadway play. They've taken a liking to each other, but Robert tells her that he is also The Alcoholic, and only recently gotten sober, so it is not a good idea for them to start a relationship. She agrees, and they shake hands and agree to concentrate on the play. Cut to several months later, with Mr. and Mrs. Wilcox in some New York flophouse, drunk and flat broke.
- Gold Digger: John Howard, tennis player, and Diana's second husband. They leech off of her mother for a while, but when Michael throws them out of the house John dumps her. He makes a point of telling Diana he never liked her.
- Maybe Ever After: In the last scene Diana is off to meet the literary agent who wants to collaborate with her on her memoir. She's almost there when she runs into Linc, her old high school boyfriend. Linc is obviously interested in rekindling things, but Diana demurs, knowing she has to get her own life back in order before she can start a relationship. As she gets on the bus she says "Maybe I'll call", and they gaze at each other wistfully as the bus pulls away.
- Meet Cute: Inverted when Robert first meets Diana by entering her train compartment, and finds her in a heap on the floor, unable to get up because she's so drunk.
- Off-into-the-Distance Ending: The bus drives away with Diana, who is off to meet her agent to write Too Much, Too Soon.
- Pool Scene: A pool scene shows off Dorothy Malone in a swimsuit, and also shows how Diana is throwing a party because her first husband has gone off to shoot a movie and she can't stand to be alone.
- Rage Against the Reflection: An extremely intoxicated Diana is fired from her crappy job performing at a burlesque club. She is stumbling down the street when her attention is caught by some advertising posters in a drugstore window. Diana is imitating the models in the posters when she catches sight of her own face in the glass. She smashes the window, climbs in, and wrecks the whole display. This is what gets her involuntarily committed to a sanitarium for alcoholics.
- She's Got Legs: When Diana first comes to LA to make movies, the paparazzi at the train station encourage her to hike her skirt up and show some leg. When her father shows up, Diana drops the skirt.
- Shout-Out to Shakespeare: Egged on by some friends on a neighboring party boat, a drunk John Barrymore reels off the "once more unto the breach" speech from Henry IV, hitting it out of the park before he stumbles over the railing and falls into the water.
- Tomboyish Name: Diana's mother is named Michael. In Real Life the former Blanche Oelrichs originally adapted "Michael Strange" as a pen name but started going by it in her regular life as well.
- Very Loosely Based on a True Story
- Diana signs with a fictional film studio making fictional movies. She is shown to quit after one film, when both it and her are received poorly. In fact, Diana Barrymore made six mediocre films before her addictions ended her acting career.
- The film shows her starting drinking out of guilt after her father's death. In fact it was John Barrymore, Father of the Year, who started teenaged Diana's alcohol habit.
- Her first husband Vincent Bryant is a fictional character, apparently because the studio was afraid of libel.note Her once-boyfriend Linc, who shows up in the final scene to give Diana some hope, is also fictional.
- There were multiple sanitarium stays, not just the one as shown in the film. The movie also omits one of her low points, when she was hired to appear in The Diana Barrymore Show—it would have been the first TV talk show ever—only for the show to be cancelled when Barrymore literally failed to show up.