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Jim Hardy (Crosby), Ted Hanover (Astaire) and Lila Dixon (Virginia Dale) form a musical act together in Manhattan. Jim wants to retire with Lila, to whom he is engaged, and live on a farm he's purchased in Connecticut. However, Lila loves Ted, and so Jim retires alone to his farm... or attempts to.
After nearly a year of attempting to run a farm, a nervous breakdown, and a brief stay at a sanitarium , Jim returns to Manhattan on Christmas Eve to see his old friends. He has what he thinks is a brilliant idea - he wants to convert the farm into an entertainment venue called Holiday Inn, which will only be open on holidays. Ted and Danny Reed (Hanover's agent) scoff at the plan.
Danny stops at a flower shop in the airport, where he is recognized as an agent by Linda Mason (Marjorie Reynolds) who asks him for a job. To brush her off, he directs her to Holiday Inn, and gives her a ticket to Ted and Lila's show. She goes, as does Jim, who pretends to be the owner of a big club. She, in turn, pretends to be a friend of Ted's and a celebrity. Ted and Lila come to the table after the performance, and Linda promptly flees.
The next morning, Linda arrives at the Holiday Inn, and she and Jim realize that both were fooling the other the previous evening. They sing "White Christmas" together.
On New Year's Eve, Holiday Inn finally opens to a packed house. Meanwhile, in Manhattan, Ted finds that Lila has left him for a Texas millionaire, and goes out to Holiday Inn, thoroughly drunk. He dances with Linda, proceeds to bring down the house blind stinking drunk, and then promptly fall unconscious. Danny arrives at the Holiday Inn just as Ted is carried upstairs.
The next morning, Ted awakens at the Inn with a hangover and no memory of the previous night. Danny, however, is thrilled that Ted has found a new partner, but dismayed when neither he nor Ted can identify the girl. Jim, of course, knows Linda, but does not give any information away, as he fears that Ted will take Linda away from the inn.
Then comes Lincoln's Birthday. In an attempt to disguise Linda, Jim decides that all of the performers and musicians will perform in Blackface. Ted and Danny return, and attempt to find Linda, but their search proves fruitless. Jim sort-of proposes to Linda, who accepts and declares that they are sort-of engaged.
At the rehearsal for Valentine's Day, Jim sings "Be Careful, It's My Heart" to Linda, who begins dancing. Ted and Danny arrive, and Ted dances with Linda. The music abruptly halts as Jim sees Ted dancing with Linda. Danny suggests that Ted and Linda open their new act at the Inn, on Washington's Birthday. Jim dejectedly concedes.
Washington's Birthday arrives, and Ted and Linda dance in elaborate 18th century costumes and wigs. However, whenever they try to kiss, Jim changes the music from the period minuet to jazz.
On Independence Day, Ted and Danny have arranged for Hollywood representatives to be at the Inn to determine whether or not Ted and Linda are suitable for film. Jim, overhearing their plan, bribes the hired hand Gus (Irving Bacon) to ensure that Linda does not arrive at the Inn. Gus picks up Linda in the Inn's car, and drives it into a creek. Linda attempts to hitchhike back to the Inn, and is picked up by Lila. Lila, it seems, has left her Texas millionaire after he turned out to [[Pun|owe millions rather than own them. Learning this, Jim summoned her to the Inn to re-partner with Ted. Linda drives Lila's car into the same river where Gus is still stranded. At the Inn, Ted improvises a solo dance with firecrackers. Linda arrives, is furious at Jim, and accepts Ted's offer to do motion pictures with him. The Hollywood representatives want to make the film about Holiday Inn; Jim reluctantly agrees.
At Thanksgiving, the Inn is closed, and Jim is depressed. He plays his Thanksgiving song on the record player, and makes bitter self-deprecating jokes over the lyrics. His housekeeper Mamie (Louise Beavers) tells him to go to California and win back Linda.
In California, on Christmas Eve, Ted is prepared to elope with Linda after the night's shooting, which would complete the film. Jim runs into Ted and Danny, who realize what he is doing and attempt to lock him in a closet. It backfires, and Jim locks them in their dressing room. Jim walks around the set, which is a recreation of Holiday Inn. He leaves his pipe on the piano, and hides. Linda comes to the studio, and filming begins. She recognizes the pipe, and runs to Jim.
Finally, New Year's Eve at the Holiday Inn features a reprise of Jim, Ted, and Lila's old act, with Linda added in. Jim and Linda stay at the Inn, while Ted and Lila, reunited, go off to a life of showbiz.
Holiday Inn is the Trope Namer For:
Holiday Inn contains examples of:
- Accidental Innuendo: "The two of us, dedicating our lives to making people happy with our feet."
- "What is this, a daisy chain?"
- American Accents: Gus has a fairly standard movie Down East accent.
- Bedsheet Ladder: Ted and Danny use one to escape from Ted's upper-floor dressing room after Jim locks them in.
- Black Like Me: Imposed on Linda by Jim for the show on Lincoln's Birthday, to keep Ted and Danny from identifying her.
- Book Ends: The film opens and ends on the night before a holiday (Christmas and New Year's). We have a musical number in both cases as well: Ted, Lila and Jim's nightclub act at the beginning, the finale in the Inn at the end. Also, both numbers are versions of the same song.
- The Cameo: The fellow at the artists' table in the club near the beginning of the movie? One of the other members of "The Rhythm Boys", the band Bing was in when they first got into movies. The nightclub orchestra leader? Harry Barris, another member.
- Chuck Jones: The animated Thanksgiving turkey.
- Deadpan Snarker: Both Jim and Ted get in some good lines.
- Defictionalization: Sortakinda. The "Holiday Inn" hotel chain is named for this movie.
- Dreaming of a White Christmas: The song is sung twice, with the result that the trope name is uttered so often it ought to count as Arc Words. Also, of the three Christmases the film spans, two of them are snowy (the third is in California).
- Drowning My Sorrows: When Lila dumps Ted (by telegram), he orders scotch and soda -- "a bottle of each," according to maitre d' Francoise -- and consumes both entirely.
- Freak-Out: Jim undergoes a breakdown when the stress of running the farm entirely by himself becomes too much for him, and ends up spending what is implied to be several months in a sanitarium recovering.
- Gold Digger: Lila dumps Jim for Ted to keep making (more) money in show business. Lila dumps Ted for an unnamed Texas millionaire. Lila dumps millionaire when she finds out he's actually broke. Can we say "Lila"?
- Greed: Danny Reed. Lila, too, but Danny is crass about it.
- Hangover Sensitivity: Ted demonstrates this on New Year's Day.
- Hey, Let's Put on a Show: Jim's solution to what to do with the farm when it proves impossible for him to work it by himself: turn it into a nightclub!
- High Concept: The movie was born from an abandoned idea Irving Berlin had for a Broadway show, which could basically be summed up as "Holidays: The Musical!"
- Hollywood New England: Midvale, Connecticut. In 1942 it's incredibly rural, and the train stops only if you flag it down, but somehow it's still close enough that New York club-goers can get to it easily. It's probably a bedroom suburb of New York City today.
- Idiosyncratic Wipes: A shot of an ornate calendar page zooms in on the appropriate holiday each time the movie jumps forward in time.
- Irving Berlin: Creator of the concept, composer, lyricist...
- It's All About Me: Danny. His only reaction to Jim getting Linda back was, "The world can't do this to me!"
- Jerkass: Danny Reed.
- Lack of Empathy: Danny. In the wake of the July 4th fiasco which ended up with Jim and Linda broken-hearted, Ted obviously distressed about the breakup despite getting the girl out of it, and a movie deal in the offing, Danny's only thought is how happy he is for the movie deal, and he assumes everyone else is, too.
- List Song: "Song of Freedom", Jim's number from the July 4th show, incorporates a list of American freedoms.
- Love Triangle: First, Ted and Jim are both in love with Lila, who is also in love with both of them. Then, Jim and Ted both love Linda, who loves Jim and likes Ted.
- Love You and Everybody: Lila claims something like this early in the film when speaking with Ted:
Lila: I love you... and Jim. I love everybody!
- Mammy: Mamie.
- Messy Hair: Jim's colonial-era wig during the Washington's Birthday show.
- Method Acting: Fred Astaire was really drunk for the drunken dance: he took two shots of bourbon before the first take, and another shot before each additional take. What ended up in the final film is something like the seventh take.
- Mock Millionaire: The act that Jim and Linda give each other when they first meet is basically this without props.
- Montage: Ted and Linda in Hollywood.
- My Friends and Zoidberg: Danny introducing the other characters to the Hollywood men on July 4th:
Danny: This is Ted Hanover and Linda Mason... And the owner, Jim Hardy.
- Subverted when the Hollywood men immediately zero in on Jim, ignoring Ted, Linda and Danny.
- Nice Hat: Linda acquires a couple through the course of the film.
- Ted's top hat on New Year's Eve certainly counts.
- Noodle Incident: What happened between the director's "Cut!" and Danny and Ted getting into the soundstage:
Danny: How could he get that far in five minutes?
- Off-Screen Breakup: Lila's breakup with the millionaire. We get it entirely second-hand.
- Oh Crap: Jim's reaction when Linda finally makes it to the Inn on July 4.
- The Oner: The sequence being filmed during the movie's climax is an immensely-extended single shot -- so much so that it could never be done in a real filming situation. For example, the director and cameraman somehow switch from an "exterior" boom camera to an "interior" dolly without interrupting the shot.
- Patriotic Fervor: A straight example in Jim's July 4th number.
- Pimped-Out Dress: Every female performer on Washington's Birthday, but especially Linda.
- Pretty in Mink: Linda, during the filming of the movie-within-a-movie.
- Ted's fur-trimmed coat on New Year's Eve.
- Princess for a Day: Linda's description, almost word-for-word, of what it's like for her to perform at Holiday Inn.
- Sassy Black Woman: Mamie is a very relaxed individual overall, but when she gets her dander up...
- Second Act Breakup: And first, and third... hell, this movie is studded with breakups, all of which directly drive the plot. First, Lila breaks her engagement with Jim to be with Ted (allowing Jim to meet Linda). Then she breaks her engagement to Ted to run off with a Texas millionaire (allowing Ted to discover Linda and plot to take her from Jim). Then she breaks her engagement to the millionaire because he's broke (which makes her available to distract Ted from Linda). Jim and Linda's sort-of engagement is broken as part of the July 4th debacle (which is the real Second Act Breakup, because it sets the stage for the conclusion of the film). And then Jim finally returns the favor by breaking up Ted and Linda by winning Linda back (plot resolution).
- Self-Deprecation: Jim's bitter comments about himself and his life on Thanksgiving.
- Movie Within A Movie: They actually used the movie's sets as the sets for the movie-within-the-movie.
- Spiritual Successor: White Christmas was intended to be one to Holiday Inn, and still managed it despite cast changes and massive rewrites.
- Technology Marches On: Several very obvious examples, ranging from a console record player to a studio telephone that's useless because the operator has gone home for the night.
- Telegraph Gag STOP: Averted by Lila's telegram to Ted.
- Tempting Fate: Danny, reassuring Ted on the last night of shooting:
Danny: What could possibly go...
- Too Good to Last: Jim's exact words when he learns everyone else is in favor of the film deal.
- Values Dissonance: The "Abraham" number for Lincoln's Birthday: a minstrel show in Blackface and dialect, and Majorie Reynolds done up as a pickaninny.
- What Could Possibly Go Wrong?: Danny almost manages to complete this entire phrase, and still ends up bringing disaster down upon his plans for Ted and Linda.
- What Did I Do Last Night?: Ted, on New Year's Day.