Holiday Inn is a delightful 1942 film, sweet without being maudlin, which showcases Bing Crosby and Fred Astaire.

Fred and Bing play old friends and competitors. They have a nightclub act in which Bing sings and Fred dances, competing for the affections of Virginia Dale. Astaire, we are led to believe, is an old rake, very effective at seducing women, especially Crosby's girlfriends.

At the start of the movie, Crosby retires from show-biz to run a farm and Astaire runs off with his (Crosby's) fiance, their partner Virgina Dale. The farm proves boring, so Crosby converts it into "Holiday Inn", a hotel open only for major holidays, and offering world-class nightclub performances. This means that we get to see a song and dance number for every major holiday; this is the organizing theme for the movie.

Spoilers start here

Virginia Dale soon dumps Astaire as well and, distraught, he makes his drunken way to Holiday Inn. There he dances with Crosby's new singing partner, the beautiful Marjorie Reynolds. He falls for her utterly, but Crosby has also fallen in love with her and knows that Astaire will steal her away. He manages to hide her identity for over a month.

However, once the truth comes out, Astaire turns on the charm and Reynolds falls for him. They continue to perform together at Holiday Inn, though Crosby intervenes whenever Astaire is about to work a smooch into their routines.

Hollywood talent scouts discover the operation and commission a film about it (is it the very film we are watching? Very post-modern). Astaire and Reynolds depart for Hollywood to film the movie and get married, while Crosby stays behind and mopes.

At the 11th hour, he realizes that he must take drastic action to win the woman he loves. He departs for Hollywood, arriving just as they are filming Reynolds's last scene (her rendition of White Christmas, sung to her lost lover in the movie-within-the-movie). Crosby breaks into harmony with her from off-set and she weeps, realizing that he is the only man she has ever loved.

Virginia Dale comes back to Astaire too, so he is not left alone.

End spoilers

In the movie, Astaire is expected only to dance, and Crosby only to sing. Nobody works outside his or her areas of greatest skill. Also, the plot requires no weird bursting into song; every song and dance number fits the story.

The score is by Irving Berlin and I won't list every song here. However, three numbers deserve particular mention

  1. White Christmas. This song is performed twice, once near the beginning of the film, and again near the end. It was an instant hit, and deservedly so.
  2. Fred Astaire's drunken New Year's dance. He shows up at Holiday Inn, three sheets to the wind, having been dumped by his fiance, then dances with Marjorie Reynolds. Apparently he actually got drunk before doing the number. His performance is masterful.
  3. The Lincoln's Birthday number, in blackface, is offensive to modern viewers. I am certain they edit this out when showing the movie on American television. Worth seeing as evidence of how much American sentiments have changed since World War II.

(The song Easter Parade became another classic, but it does not compare with White Christmas or the New Year's number).