- Channel Hop: Paramount made six of the total seven films yet they lost the rights to all the ones that they produced. The first four movies are now owned by Universal because they own Paramount's pre-1950 library, Road to Rio is owned by Sony Pictures Television and Fremantle Media while Bali fell into public domain, and the final one, The Road to Hong Kong was made by United Artists and they still own it to this day albeit through their parent company Metro-Goldwyn-Mayer.
- Dueling-Stars Movie: Bob Hope and Bing Crosby made a long-running gag of this, both in and out of the movies they appeared in together.
- Fake Nationality: Numerous examples, though one particular stand out is Peter Sellers as an Indian in The Road to Hong Kong.
- Harpo Does Something Funny: A fair amount of the pictures consisted of this, despite the fact that a script theoretically existed.
- Production Posse: Jerry Colonna, who was a long-time castmember on Hope's radio and TV shows, appeared in three of the films.
- Real-Life Relative: Bob Crosby, Bing's brother, has a cameo in Road to Bali.
- Those Two Actors: Hope and Crosby.
- Throw It In!: The most memorable incident involves a camel.
- Wag the Director: In The Road to Hong Kong, it was Bing Crosby who thought that Dorothy Lamour was too old to be a leading lady, resulting in the female lead being given to Joan Collins. Bob Hope, in turn, protested at this, and refused to do the film without Lamour. Lamour's extended cameo that featured her singing towards the end of the film was the result of this as a compromise.
- What Could Have Been:
- The first film, Road to Singapore, was at one point planned as a vehicle for George Burns and Gracie Allen.
- An eighth film, Road to the Fountain of Youth, was planned in the late 1970s but called off after Bing Crosby's death.
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