The 1956 film:

All-Star Cast: Bing Crosby, Frank Sinatra, Grace Kelly and Louis Armstrong were all famous by this point; and both Celeste Holm and John Lund, although lesser known, had been already in several critically acclaimed productions before this.
Breakaway Pop Hit: "True Love", later became this in 1993 for Elton John and Kiki Dee (#21 AC).
Dueling-Stars Movie: Frank Sinatra and Bing Crosby were the two most popular singers of their day. In this movie, they sing a duet.
Non-Singing Voice: Averted; despite initial plans to dub her, Kelly sang her own (small) part in 'True Love', which became a gold record.
Referenced by...:
- In the Fantasy Island episode "Escape/Cinderella Girls," two women get to live as glamorous heiresses for a weekend, complete with a change of wardrobe. One of them looks at a dress provided and says, "It looks just like the one Grace Kelly wore in High Society!"

Trivia / High Society