1940 – If I Had My Way

If I Had My Way (1940, Universal)

As “Buzz Blackwell”

Cast: Gloria Jean, Charles Winninger, El Brendel, Alyson Joslyn.

Director / Producer: David Butler

Screenwriters: William Conselman & James V. Kern from a story of David Butler, William Conselman & James V. Kern.

Summary: A heartwarming Crosby vehicle in which bridge-worker Bing helps an orphaned little Gloria find her rightful guardian. A colorful cast of character actors and vaudevillian performers round out this charming film, showcasing Bing’s talents for working with young people.

Featured Songs:

  • ”Meet The Sun Halfway”
  • “I Haven’t Time To Be a Millionaire”
  • “Pessimistic Character”
  • “If I Had My Way”
  • “April Played The Fiddle”


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1940 – Rhythm on the River

Rhythm on the River (1940, Paramount)

As “Bob Sommers”

Cast: Mary Martin, Basil Rathbone, Oscar Levant, William Frawley

Director: Victor Schertzinger

Producer: William Le Baron

Screenwriter: Dwight Taylor from a story by Willy Wilder & Jacques Thery

Summary: A breezy musical with Crosby ghostwriting music for Rathbone and meeting up with Martin, never dreaming that she’s been hired to ghostwrite the lyrics. The two hoodwinked songwriters team up for more than music and lyrics in this heartwarming romance!

Featured Songs:

  • “Only Forever”
  • “When The Moon Comes Over Madison Square”
  • “Rhythm On The River”
  • “That’s For Me”
  • “What Would Shakespeare Have Said”


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1940 – Road to Singapore

Road to Singapore (1940, Paramount)

As “Josh Mallon”

Cast: Dorothy Lamour, Bob Hope, Charles Coburn, Judith Barrett, Anthony Quinn.

Director: Victor Schertzinger

Producer: Harlan Thompson

Screenwriters: Frank Butler & Don Hartman

Summary: Bing and Bob swear off women, hiding out in Singapore; then they meet saronged Lamour. This marks the beginning of the successful and long-running series of ‘Road’ pictures, which established the formula for the ‘buddy picture’ genre.

Featured Songs:

  • “Sweet Potato Piper”
  • “Captain Custard”
  • “Too Romantic”
  • “The Moon and the Willow Tree”
  • “An Apple For The Teacher”


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1940 – Swing With Bing

Swing With Bing (1940, Universal)

As himself

With Andy Devine, Byron Nelson, Jimmy Demeret

Summary: A short-subject golf film at the fourth annual Bing Crosby Pro-Am at Rancho Santa Fe. This sport short film had been a long-pursued idea of Bing’s and the PGA participated in the filming.

Featured Song:

“The Little White Pill On The Little Green Hill”


1941 – Birth of the Blues

Birth of the Blues (1941, Paramount)

As “Jeff Lambert”

Cast: Mary Martin, Brian Donlevy, Carolyn Lee.

Director: Victor Schertzinger

Producer: B.G. DeSylva

Screenwriter: Harry Tugend & Walter DeLeon from a story by Harry Tugend

Summary: A fictionalized Hollywood telling, loosely based on the career of the Original Dixieland Jazz Band, to illustrate the origins of Jazz. As a young musician, Jeff Lambert is brought up on classical music, but longs to explore the creole sounds emanating from Bourbon Street in New Orleans. A safe, but interesting look at this unique time in music history, this film superbly blends drama, comedy and great music. Legendary trombonist, Jack Teagarden is featured and Bing later recalled this as one of his favorite movies.

Featured Songs:

  • “Birth of the Blues”
  • “St. James Infirmary”
  • “Memphis Blues”
  • “By The Light of the Silvery Moon”
  • “My Melancholy Baby”
  • “The Waiter and the Porter and the Upstairs Maid”
  • “St. Louis Blues”


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1941 – Road to Zanzibar

Road to Zanzibar (1941, Paramount)

As “Chuck Reardon”

Cast: Bob Hope, Dorothy Lamour, Una Merkel, Eric Blore.

Director: Victor Schertzing

Producer: Paul Jones

Screenwriters: Frank Butler & Don Hartman from a story by Don Hartman & Sy Barlett

Summary: In the second installment of the ‘Road’ Pictures, Bing and Bob are circus performers traveling through the jungle with Lamour and Merkel, looking for a diamond mine.

Featured Songs:

  • “It’s Always You”
  • “You Lucky People You
  • “You’re Dangerous”
  • “On The Road To Zanzibar”
  • “Birds Of A Feather”


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1942 – Holiday Inn

Holiday Inn (1942, Paramount)

As “Jim Hardy”

Cast: Fred Astaire, Marjorie Reynolds, Virginia Dale, Walter Abel.

Director/Producer: Mark Sandrich

Screenwriter: Claude Binyon

Summary: Entertaining musical about a romantic triangle and the establishment of a country inn that’s only open on holidays. A memorable array of holiday-themed songs by the great Irving Berlin (featuring the debut of the all-time classic ‘White Christmas’) provide the foundation for Bing’s stellar crooning and Fred Astaire’s divine dancing!

Featured Songs:

  • “I’ll Capture Your Heart”
  • “Lazy”
  • “White Christmas”
  • “You’re Easy To Dance With”
  • “Let’s Start The New Year Right”
  • “Abraham”
  • “Be Careful, It’s My Heart”
  • “Easter Parade”
  • “Song of Freedom”
  • “I’ve Got Plenty To Be Thankful For”


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1942 – My Favorite Blonde

My Favorite Blonde (1942, Paramount)

As “Man Giving Directions” (cameo appearance).

Cast: Bob Hope, Madeleine Carroll.

Director: Sidney Lanfield

Screenwriter: Don Hartman & Frank Butler from a story by Norman Panama & Melvin Frank.

Summary: Bob and his trained penguin become sitting ducks when a spy uses them to help deliver secret orders.