Bob Hope & Bing Crosby’s 7 Road Movies, Ranked Worst To Best

Some double acts have made such an impact that they’ll never be forgotten. Laurel and Hardy, Lemon and Matthau, and Key and Peele have etched their names in the history books, some of the best pairings of Hollywood’s Golden Age. Then, there are those lesser-known Golden Age Hollywood actors who have created some fantastic moments together but can live in a hazy memory that gets revisited from time to time. Bing Crosby and Bob Hope were enormous stars in their own right, and are probably most remembered for their solo achievements. Crosby’s White Christmas gets replayed every year around the holidays, and Hope is still considered one of the best Academy Awards hosts in history.

When they joined forces in the Road To… series of films, they created the kind of movie magic that Old Hollywood comedy movies can produce. With laughs aplenty, and the glamorous addition of Dorothy Lamour, these comedies were more than just for laughs. They offered a clever satire on the popular films of the time, made several humorous references to other famous actors, and had Hope break the fourth wall, addressing the audience directly for comedic effect. The series was extremely popular with audiences and an eighth film was planned but had to be scrapped due to Crosby’s sad passing.

7 Road to Hong Kong (1962)

Two con artists and a cameo

The last in the series, this was the only film not to be made with Paramount Pictures. It was directed by Norman Panama and, along with the three regulars, starred Joan Collins and Peter Sellers. The theme seemed very much like an homage to the James Bond-style spy genre, yet it predated 007’s first official cinema outing in Dr. No, which came out later that same year. Production was tinged with a bit of negativity as Bing Crosby thought Dorothy Lamour was too old to play a leading lady at 48, which was why Collins was brought in. Bob Hope said he wouldn’t do the movie without her, so she joined for a musical cameo as a sort of compromise.

The film wasn’t as well-received as the previous installments, possibly due to the 10-year gap between this film and the one before. Lamour’s absence could really be felt in the dynamic, and the older stars were outshone by some of the fresh-faced newcomers. It holds a score of 60% on Rotten Tomatoes, which is the lowest of the series. It did include some impressive cameos, most notably one from Frank Sinatra and Dean Martin.

6 Road to Bali (1952)

Two show-biz friends and a princess

The first, and only, film in the series to be filmed in glorious technicolor, the sixth installment focused on a love triangle between the three leads, set on a paradise island. Hal Walker directed it, and the exotic setting looked very impressive in color. There’s a giant squid, a cameo from Jane Russell, and quite a lot of fourth-wall breaks. Hope hilariously encourages the viewers to get some popcorn while Crosby sings, and the crooner gets his own moment with a shrug to the camera.

The film did well at the box office, earning $3 million and holds a 75% rating on Rotten Tomatoes. Critics praised the chemistry between the three actors, and it features one of the most humorous endings in the franchise. As Bing Crosby walks off not only with Lamour’s character but also Jane Russell, Bob Hope is left pleading with the director not to let the film end. This final fourth wall break was very well-executed and ensures viewers finish the experience with a big smile on their faces.

5 Road to Zanzibar (1941)

Two con-artists and a beautiful woman

Directed by the prolific Victor Schertzinger, this is the second installment in the series of seven. The focus of this comedy musical is the popular at the time, safari genre. So much so, that the original draft of the film was deemed too similar to a 1939 picture, that it was revised as a spoof of sorts. Riding high off the success of the first film, the trio returned for another outing. With a big emphasis on the jokes and gags, rather than a cohesive plot, the characters jump from situation to situation via the medium of song, dance and laughs.

The various twists involving multiple layers of deception and confidence schemes, make for a fun watch, but time has not been kind to some of the themes and attempts at humor. This is a common thread in all the films, to varying degrees, so viewers should be prepared for a very different time in history to be depicted. It holds a 89% score on Rotten Tomatoes, and was extremely successful at the box office.

4 Road to Morocco (1942)

Two castaways and a princess

The third film to be released in the series, it came out just a year after its predecessor. It was the fourth highest grossing film of 1942 and was chosen to be preserved in the US National Film Registry for its cultural significance. Focusing on the popular theme of shipwrecks and castaways, as well as some royal intrigue, it co-stars Anthony Quinn and Dona Drake. It received the best reviews to date, and audiences couldn’t get enough of its three stars.

With a 79% score on Rotten Tomatoes, the picture also received two Oscar nominations, including one for Best Original Screenplay. It also saw great success with one of the songs on the soundtrack, as Moonlight Becomes You was a Billboard Number 1 hit for Bing Crosby. It also broke boundaries with one of the first romantic interracial kisses on screen.

3 Road to Singapore (1940)

Two playboys and a beautiful dancer

Kicking off the series in style, this wacky film was a great introduction to what was to come. It set up some of the running jokes that became a staple in the subsequent outings. There was a gag about Bing Crosby’s waistline, a patty-cake prelude to a fistfight, and cons that are a cause of a lot of the action. It also began the trend of Hope and Crosby ad-libbing a lot of their scenes. Anthony Quinn also co-starred and Victor Schertzinger directed, both of whom would be back for subsequent productions.

There’s something special about seeing how the relationships and chemistry between the three actors develop, and it’s plain to see the magic that was being made on screen. The film had great reviews and was an immediate success, leaving audiences wanting more. Little did they know at the time that they would indeed receive the gift of six more movies. It has a 100% rating on Rotten Tomatoes, and has the honor of being the one that started it all.

2 Road to Rio (1947)

Two vaudevillians and a hypnotized niece

Set on the high seas, the Norman McLeod-directed installment is the fifth in the franchise. With character names that include Scat Sweeney and Hot Lips Barton, they are some of the more entertaining ones that Crosby and Hope got to play. With the plot involving using hypnosis for nefarious means, some very mysterious papers, and another cameo from Jerry Collona. It also saw both Bob Hope and Bing Crosby co-produce the film.

It received an Academy Award nomination for its music and has a 100% score on Rotten Tomatoes. It’s also one of the highest grossing of the franchise, having made $4.5 million at the box office. It proved that not only did the films still draw in massive crowds, but that the dynamic trio hasn’t lost any of its sparkle. Critics applauded the riotous comedic moments, as well as the roaring musical numbers.

1 Road to Utopia (1945)

Two vaudeville performers and a saloon singer

Spoofing the gold rush genre of films, the three leads head to Alaska at the turn of the century. The fourth in the series, it aptly starts with a fourth wall break and introduction by iconic satirist Robert Benchley. He explained that he was there to help understand the convoluted plot, which was an obvious play on the films’ outlandish premises. With tropes that include a flashback, cliffhanger and even a visit from Santa Claus, this is a non-stop roller coaster of action and adventure.

There are a few aspects of the film that are not in line with the others in the series, but those are the parts that make it so special. It’s the only one to be set in the past, the only one to show the characters as their older selves, and the only one not to feature a real location in its title. The scrapped eighth film would have been the second to this, with the working title of Road to the Fountain of Youth.

The musical numbers soar, and the dynamics between Bing Crosby and Bob Hope are at their best. It was nominated for an Academy Award for Best Original Screenplay, which was written by Melvin Frank and Norman Panama. What’s also interesting is that it was filmed a whole three years before its release, potentially making space for Crosby’s own Oscar campaign. It has a 100% rating on Rotten Tomatoes, and is one of the best reviewed, and highest grossing of all.