Frank Sinatra and Bing Crosby

Frank and Bing

Happy Holidays with Bing and Frank

This piece is my first contribution to the Sinatra Centennial blogathon, which I’m proudly co-hosting with Emily at The Vintage Cameo. I’m also hoping to put a second piece up before the event ends on Sunday!

They might have only co-starred in two movies, but Frank Sinatra and Bing Crosby loom large in each other’s legend. Sinatra took inspiration to start out on his singing career from Crosby’s success, while Bing jokingly spoofed Frank on film. Although best-known as singers, both were also Oscar-winning actors. They appeared together on radio and TV over the years, most famously in the TV special Happy Holidays with Bing and Frank, which has recently been resurrected – and is perfect festive viewing for Sinatra’s Centennial.

According to a biography of the young Sinatra I read a few years ago, Frank: The Making of a Legend by James Kaplan, the young Frank had a picture of Bing on his wall and wore the style of cap favoured by his idol. Once Sinatra started to make a name for himself as a singer and followed Crosby into films, comparisons were soon being made between the two.

An edition of the Motion Picture-Hollywood Magazine in December 1943 even carried an article under Bing’s byline offering kind but slightly patronising advice to “Frankie”. This piece certainly reads as if it was ghost-written by a magazine journalist, but it’s interesting reading all the same – claiming that “some people in Hollywood” had tried to start a feud between the two singers but didn’t get anywhere.

I was also amused to see the comment in the article about  “a young singer like yourself who is riding a popularity wave the like of which show business sees only about once every five or six years.”  In retrospect, what an understatement. Crosby was nearer to the mark when he famously joked: “Frank is a singer who comes along once in a lifetime, but why did he have to come in mine?” 

Sinatra in The Shining Future

Frank Sinatra in The Shining Future

The first film the two singers both appeared in was a propaganda short made to promote the sale of Canadian war bonds in 1944, The Shining Future. However, they don’t share any screen time. I’ve just seen this film and really enjoyed it. This unusual short is set in the future, in 1960, imagining life after the war – with a Canadian family who are bored of eating steak every day, and who use their own helicopter to get about, while wondering whether to upgrade to a “rocket plane”! Cars are apparently old hat.

One thing this film does get right, though, is that the family of 1960 spends a lot of time watching television. They have a handy gadget called a ‘reversometer’, something I’d love to get my hands on, which allows viewers to turn back the dial and watch films from the past – in this case, 1944. The family watches a wartime broadcast presented by Jack Carson, which begins with Sinatra performing a powerful song imagining the end of the war, There’ll Be a Hot Time in the Town of Berlin, and ends  with a swinging Crosby number urging the audience to buy bonds,  Get On The Road to Victory.  Other artists featured include Deanna Durbin and Benny Goodman and his Orchestra. However, in between all the musical numbers, the centrepiece of the film is a heart-rending plea by Cary Grant, who reads out a letter from a dead Canadian soldier. The 20-minute film was later cut down to a 10-minute version entitled The Road to Victory, retaining Sinatra and Crosby’s songs.

Here_Come_the_Waves (1)

Bing spoofed Frank in Here Come the Waves

The same year that this short was released, Crosby spoofed Sinatra’s bobbysoxer fans in the comedy Here Come the Waves, another slice of wartime propaganda,where he plays a crooner who has to choose between a pair of twins, both played by Betty Hutton. Crosby sings one of Sinatra’s hits, That Ol’ Black Magic, to an audience of swooning girls. Bing also satirised Sinatra’s fans a second time in 1945, when he provided the voice for unlikely idol Eddie Bracken in Out of This World, about an all-girl orchestra who discover a great male singer. Must admit I haven’t seen either of these as yet, but found out about their Sinatra links via  Steven Lewis’ very informative page about Crosby’s films. Here Come the Waves is due for DVD release in the UK next year, so I should be able to see it then.

Sinatra and Crosby didn’t star together on film until 1956, in High Society, the smash hit musical remake of The Philadelphia Story, where Crosby takes over Cary Grant’s lead role as C.K. Dexter-Haven and Sinatra takes James Stewart’s role as  Mike  Connor. This film is often criticised by fans of the original, but I’d have to say I love both versions, and the Cole Porter songs in the musical are wonderful.


Sinatra and Crosby performing ‘Well, Did You Evah’ in ‘High Society’.

Crosby probably has the best musical numbers in the remake, especially True Love with Grace Kelly and Now You Has Jazz with Louis Armstrong – but it’s Sinatra who sings the hilarious  Who Wants to Be a Millionaire?  Crosby and Sinatra also famously duet on Well, Did You Evah, which includes the classic moment where Sinatra jokes: “Don’t dig that kind of crooning, chum!”

The following year, Sinatra gave one of his finest acting performances in the biopic The Joker Is Wild, where he plays  Joe E. Lewis, a singer who became a comedian after his singing voice was destroyed in a violent attack. Crosby doesn’t actually appear in this film, but his voice is heard, in a memorable scene where the heartbroken Joe sits behind the scenes at a nightclub, listening to a great new singer, and is told by a well-meaning but tactless member of staff “I’m told you used to be pretty good too.” It was clearly important for this scene to find a singer whose voice could stand comparison with Sinatra’s – so to use a Crosby recording was the obvious answer.

That same year, the two made the evergreen Christmas favourite Happy Holidays with Bing and Frank, a special episode of The Frank Sinatra Show which features Bing visiting Frank and the pair performing various Christmas songs, including, of course, White Christmas.  I’m definitely going to watch this again over the Christmas break!

robin and the 7 hoods

Sinatra, Crosby and Martin in ‘Robin and the 7 Hoods’

Sinatra made a brief cameo in one of the Bing Crosby and Bob Hope Road movies, The Road to Hong Kong (1962). Then the two singers starred together again in the Rat Pack vehicle Robin and the 7 Hoods  in 1964, along with Dean Martin, Sammy Davis Jr and Columbo star Peter Falk. This comedy moves  the Robin Hood story into the Prohibition era, with Sinatra as gangster “Robbo”, who decides to share his ill-gotten gains with the poor of Chicago.

I’ll admit I find this film rather self-indulgent and slow, even though the cast seem to be having a great time – but there are some amusing scenes featuring Sinatra and Crosby, who plays ageing orphan turned press agent Allen A. Dale. The movie’s best moments, not surprisingly, are its songs, including My Kind of Town performed by Sinatra and the very funny Style, with Sinatra, Crosby and Martin all performing together.

For further reading, take a look at a hub page by Lorenzo27 which describes the differences between Sinatra and Crosby’s singing styles, and Joanna Wilson of the Christmas TV History blog’s piece about Happy Holidays with Bing and Frank. Also, here’s a trailer to give a taste of the show.




13 thoughts on “Frank Sinatra and Bing Crosby

  1. Pingback: Sinatra Centennial Blogathon Day 1 | Movie classics

  2. We’re lucky that two of the top entertainers of their day worked together as often as they did, but still leave us wanting more. I recall reading that Frank thought of Bing as a big brother, and that is a charming image.

    Thanks for the link to “The Shining Future” which I’ll definitely have to check out. I watched the Christmas special last week. It’s become my tip off for holiday viewing in recent years.

    You should enjoy “Here Come the WAVES” it has a terrific score and a lot of good-natured humour.

    Don’t forget the odd cartoon “Swooner Crooner” in which both are spoofed.


    • Patricia, thanks so much for your comment – I’m looking forward to ‘Here Come the Waves’ even more now!. ‘The Shining Future’ is an interesting oddity – a lot of fun in some parts, serious in others and with some great music. I think you’ll find it interesting.

      Thanks for mentioning ‘Swooner Crooner’ – I hadn’t come across it, but have just found this funny clip spoofing them both on Youtube:


  3. That’s a terrific article, Judy, full of interesting info on two of the best and most influential singers of the 20th century.
    I love the “Well, Did You Evah!” scene in High Society.

    Liked by 1 person

    • Thanks, Colin, very kind of you. I can’t see that scene enough – I also love them singing ‘Style’ with Dino in ‘Robin and the Seven Hoods’, but it’s not quite as sublime as ‘Well, Did You Evah!’


  4. I was never a Bing Crosby fan though I do love his Christmas album and some movies he has appeared in. I do have a soft spot for “Robin and the 7 Hoods” which as you say is a bit self indulgent. The musical numbers I felt kind of almost save it.

    Liked by 1 person

    • My mum loves Bing, so I grew up knowing his voice, but I’ve only got into his films more recently. Sounds like we agree over the musical numbers in ‘Robin and the 7 Hoods’ being the best parts of the film, even though you like the film overall more than I do.


  5. I love these two guys, and it makes me happy that they seemed to enjoy working together. I know Sinatra really respected Crosby and never forgot what he owed to his influence. I like Robin and the 7 Hoods, with “Style” being a great highlight, but High Society is the best thing to come from them. I get why people bemoan it since it’s a remake of a true classic, but come on, it gave us an amazing Cole Porter score and a good showcase for Bing and Frank. I didn’t know about the other films and spoofs you mentioned — interesting post!

    Liked by 1 person

    • Michaela, I loved High Society as soon as I saw it and was surprised to find it comes in for such a lot of stick – after all, it takes nothing away from the delight of watching ‘The Philadelphia Story’, and, as you say, it has that fantastic score. Many thanks for the comment and for joining in the blogathon!


  6. Pingback: Announcing the Sinatra Centennial Blogathon | Movie classics

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  8. What a marvelous article! Last week I was chatting with my grandpa and he said he preferred Crosby to Sinatra, by the way.
    I love the two films they work together. I have a soft spot for Robin and the Seven Hoods, because it puts together two favorites: gangsters and musicals! LOL
    And, well, I want to see the short film and the films where Bing spoofs Frank. They may be very interesting!
    Thanks for hosting this blogathon!

    Liked by 1 person

    • Thanks so much for taking part, Le! Interesting to hear your grandpa’s view – Sinatra is my favourite of the two, but I do like Crosby too. I also like both gangster films and musicals, but Robin and the Seven Hoods isn’t a favourite for me overall, though I do like some of the musical numbers. Thanks for the kind comment!


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