Best Song: "Swinging on a Star" (1944)

Scene from Going My Way

Welcome to Best Song, a new weekly column released on Sunday dedicated to chronicling the Best Original Song category over the course of its many decades. The goal is to listen to and critique every song that has ever been nominated in the category as well as find the Best Best Song and the Best Loser. By the end, we'll have a comprehensive list of this music category and will hopefully have a better understanding not only of the evolution, but what it takes to receive a nomination here. It may seem easy now, but wait until the bad years.

The Preface

The year is 1944 and The Academy is celebrating its 17th year. This was the first year that was broadcasted nationally on ABC Radio network. This was the first year the Best Picture category was limited to five nominees. This was also the first and last time that an actor was nominated for Best Actor and Best Supporting Actor for the same role (Barry Fitzgerald in Going My Way). This was the first time that film clips were used to promote the nominees. Going My Way also became the first Best Picture winner to also win Best Original Song for the Bing Crosby song "Swinging on a Star."

The Nominees

Song: "I Couldn't Sleep a Wink Last Night"

Film: Higher and Higher

Performers: Frank Sinatra, Dooley Wilson

It could just be that history has made the sound of Frank Sinatra a lot more pleasing to the ear, but this song is really good. Whether it is the vulnerable voice singing about not having his favorite drink or not sleeping, he manages to turn a song of yearning and turn it into something sort of beautiful. I will admit that the strings that appear randomly kind of take away from the naturalism, but that is only within this scene. As a whole, this is a nice little song that captures something simple and specific in a way that makes the listener engaged. I hope that Sinatra has more of this in him because he really knows how to make loneliness into an art form.

Song: "I'll Walk Alone"

Film: Follow the Boys

Performers: Dinah Shore (uncredited)

I am unsure if this is the version featured in the film, but it is the closest that I could find. Two songs in, and there seems to be a vibe of songs about loneliness. I must admit that I like the way that this song does its backing harmonies. It adds a beautiful melancholy to the whole thing, turning a simple stroll into a poetic experience. It helps that Dinah Shore (I think) also has a sultry voice and knows how to sound reflective in tone. I think this song works largely because of the production that fuels the track and emphasizes the vocalist nicely without just providing a bland beat behind her.

Song: "I'm Making Believe"

Film: Sweet and Low-Down

Performers: Lynn Bari

I am confident that there was more to this song, as it cuts abruptly as the horns come in. However, I am unsure if I should trust other sources. What I like about the song is that in its brevity, it manages to sing something romantic and beautiful. It also has a nice way of wrapping up in a little over a minute and giving us something nice. I don't know if I necessarily think that its shortness plays in its favor, but it doesn't outstay its welcome. As a whole, it is a good song with nothing particularly wrong except it doesn't have enough time to really earn its spot on this list of Best Original Songs. 

Song: "Long Ago and Far Away"

Film: Cover Girl

Performers: Gene Kelly, Rita Hayworth

I will admit that while I am not well versed in Rita Hayworth's career, her various entries onto this list has really made me appreciate her as a singer. While the song itself hits a lot of familiar beats, the production is solid and the way that she sings only compliments the tone. Thankfully, Gene Kelly knows how to hold up the back half and makes the rather repetitive love song into something above enjoyable. It transcends the basic function of a love song and skids by on passion to the point of being pretty good. It isn't my favorite of songs, but it is another example of how personality can make a song better, which I am starting to realize that Hayworth had in spades.

Song: "Now I Know"

Film: Up in Arms

Performers: Dinah Shore (uncredited)

It's the return of Dinah Shore for her second uncredited nomination this year. Oh, the joy of hearing her sing in the sultry voice. While the other song is full of solid production values that emphasize her personality better, this song falls more into the camp of being familiar. There's nothing wrong with it. It is just another love song in a category that has had dozens of nominees that have sounded like this already. I know that sometimes context makes a difference, and I am sure if given enough time I'd make many reconsiderations, but the song should be able to stand on their own. I don't necessarily believe that this one does. It just manages to be pleasant in a way that isn't awful. If it wasn't for this nomination, the song would likely be forgotten to history.

Song: "Remember Me to Carolina"

Film: Minstrel Man

Performers: Benny Fields

The song itself is fine. I wish that I could appreciate these slower, ballad-type love songs with deep vocals. There's a certain disconnect that has kept me from appreciating them more. In fact, I kind of don't like the song because of how slow and unmemorable it is. Yes, there's romanticism at its core and it does have a playfulness that makes it kind of fun. I can see why this was nominated, but it still is a slow song that out of context doesn't have much of an impact. Like other songs in this column, it is capable of being just good, but there's also the unfortunate dated nature of a lot of these that keeps them from making a mark on modern audiences.

Song: "Rio de Janeiro"

Film: Brazil

Performers: Ned Washington

There's an interesting subgenre of Best Original Song nominees that seem to exist almost exclusively as tourism songs. This is the latest to suggest that there's this great, grand adventure of love in South America. I don't know a lot about how this continent was depicted during this era, but the exotic nature almost suggests that it was American film's go to destination, whether it be because of the war or less obvious reasons. I don't find much fault with this song or its embrace of the familiar style. I like that there's some sense that not liking the place makes you allergic. This song has plenty of personality, but it also is kind of too goofy and touristy to really make an impact. I get why it would be nominated, but I want to better understand why South America was so alluring to audiences in the 40's that they kept writing songs about it.

Song: "Silver Shadows and Golden Dreams"

Film: Lady, Let's Dance

Performers: None

I did some research to try and find the song that was nominated. I unfortunately am unsure if this is it. However, it is also the only form of media that is available online of the film that can be accessed for free. While I won't count the song on this list, as I fear that I would judge for the wrong material, I feel that you at least deserve a chance to look at what the film looks like.

Song: "Too Much in Love"

Film: Song of the Open Road

Performers: Jackie Moran

It is interesting that this particular recording begins with someone claiming that the singer is going to over-emphasize things. It is a common issue with songs on this list. While the rhythm is tepid and fine, I don't necessarily come away feeling that the song is great. In fact, it is almost too simple to actually be interesting. Among the list of songs here that deal with romance, this one barely manages to do anything of substance with its lyrics and ends up producing a song that tries to under-emphasize its point. Maybe the abrupt ending of this cut hides something greater, but there's not a whole lot that I really enjoyed about this song that I haven't heard several times before.

Song: "The Trolley Song"

Film: Meet Me in St. Louis

Performers: Judy Garland

First off: I always thought that this was Shirley Temple. Second off: I am starting to realize that I have a soft spot for Judy Garland. While she hasn't made a strong presence on my favorites lists below, she continually brings something endearing to the game. She is a great singer and her youthful charisma allows all of her songs to unveil something deeper and far more interesting about the silly romances that she sings about. Speaking as this was the first time that I heard "The Trolley Song" in its entirety, I didn't realize how full of detail and exuberant it actually was. I come away more enamored by it and am glad to see that in a strong lull period that there's room for some fun songs like these.

The Winner

Song: "Swinging on a Star"

Film: Going My Way

Performers: Bing Crosby

It almost seems criminal that Bing Crosby has my least favorite song on Best Song to date. This is notably because he is just impeccably charming every other time he steps up to the plate. Following "White Christmas" two weeks ago, he returns with a song that reflects everything that is great about him. His voice is so rich that when he's dropping comical rhymes, it sounds more like a lesson in being responsible and cool than just being goofy. While it helps that I have seen the film and written about it extensively, it also just helps that Crosby is just great at his job. This easily ranks among the best to date, and I cannot deny the enjoyment I get out of listening to this song.

Best Loser

A comprehensive list and ranking of the songs that were nominated but did not win. This is a list predicated on which song that was nominated I liked the best.

1. "Carioca" - Flying Down to Rio (1934)
2. "Boogie Woogie Bugle Boy of Company B" - Buck Privates (1941)
3. "They're Either Too Young Or Too Old" - Thank Your Lucky Stars (1943)
4. "Cheek to Cheek" - Top Hat (1935)
5. "I've Got a Gal in Kalamazoo" - Orchestra Wives (1942)
6. "The Trolley Song" - Meet Me in St. Louis (1944)
7. "Waltzing in the Clouds" - Spring Parade (1940)
8. "Dust" - Under Western Stars (1938)
9. "I Poured My Heart Into a Song" - Second Fiddle (1939)
10. "Remember Me" - Mr. Dodd Takes the Air (1937)
11. "I've Got You Under My Skin" - Born to Dance (1936)

Best Best Song

A comprehensive list and ranking of the songs that won this category. 

1. "Somewhere Over the Rainbow" - The Wizard of Oz (1939)
2. "The Way You Look Tonight" - Swing Time (1936)
3. "Swinging on a Star" - Going My Way (1944)
4. "White Christmas" - Holiday Inn (1942)
5. "Thanks for the Memory" - The Big Broadcast of 1938 (1938)
6. "The Last Time I Saw Paris" - Lady Be Good (1941)
7. "When You Wish Upon a Star" - Pinocchio (1940)
8. "You'll Never Know" - Hello, Frisco, Hello (1943)
9. "The Continental" - The Gay Divorcee (1934)
10. "The Lullaby of Broadway" - Gold Diggers of 1935 (1935)
11. "Sweet Leiulani" - Waikiki Wedding (1937)