Best Song: "High Hopes" (1959)

Scene from A Hole in the Head

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 1959 and The Academy is celebrating its 32nd year. Director William Wyler breaks records with Best Picture winner Ben-Hur with 11 total wins. He also became the last director to win mul+tiple Best Director statues and the only person to direct three Best Picture winners. In the Best Original Song category, everyone has "High Hopes" as it wins for the film A Hole in the Head.

The Nominees

Song: "The Best of Everything"

Film: The Best of Everything

Performers: Johnny Mathis

I can see why Johnny Mathis has been consistently showing up on all of these lists. The production definitely feels a lot richer and more elegant in ways over the more classical style. Also, Mathis' wholesome voice manages to compliment the echoing melody in such a graceful way. While I will admit that the one flaw is that all of these songs sound a tad similar, they all have a consistently enjoyable quality that makes them easy on the ears. This isn't my favorite of his, but Mathis really has come to be a name that I trust. He isn't as good as Bing Crosby, Fred Astaire, or Frank Sinatra, but he's still up there of consistent favorite.

Song: "The Five Pennies"

Film: The Five Pennies

Performers: Danny Kaye

It's been awhile since Danny Kaye has come up on here. If I remember right, it was for "Thumbelina," which feels like roughly the same construct. It's Kaye singing a narrative of a cutesy children's story. While I don't know that either really have a quality of greatness to them, I can admire what they're trying to do. They're optimistic and fun, revealing morals within concepts. I think that Kaye definitely earns a place on this list, even if this song doesn't really have much that feels timeless when compared to the more produced songs on this list.

Song: "The Hanging Tree"

Film: The Hanging Tree

Performers: Marty Robbins

I will admit that there's something charming about Marty Robbins that makes this song hard to hate. For starters, the melody is simple and drives the song along just fine. It may be a detriment in some ways, making it sound even a little silly, but the rest is top notch. Robbins was an expert on writing western ballads, and the metaphor hidden within it is quite intriguing. I also like the backing vocals that appear halfway through the song to emphasize the lyrics. It isn't my favorite song, but it's definitely a strong western song that gets me in the mood.

Song: "Strange Are the Ways of Love"

Film: The Young Land

Performers: Randy Sparks

It could just be that it isn't a great year for this category, but this by far my favorite of the nominees. The lyrics may be very obvious and predictable, but I feel like there's a balance in the production that settles you into the mood. Randy Sparks' voice is tender enough to make the swooning feel real. He draws you into the simple themes of the song and makes you feel it as the melody roams around him. Overall, this is one of the better productions from this year because the melody challenges Sparks and provides something more compelling hidden underneath the lyrics. Not a great song, but definitely one that has passion to it.

The Winner

Song: "High Hopes"

Film: A Hole in the Head

Performers: Frank Sinatra, Eddie Hodges

Here's the issue. This is a great song. I feel that it has stood the test of time. However, much like "White Christmas," I don't know that I can exactly give this version a pass. It is known that I really like Frank Sinatra. Yet there's something about this duet that feels a little too raw and unformed. I don't blame the kid for his energy, but I don't know if his timing is necessarily the best. With that said, this song is one of those great affirmation songs in history. I like other versions of this a lot more. This will be tough to rank because of that bias, which isn't entirely here in 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. "That's Amore" - The Caddy (1953)
2. "The Man That Got Away" - A Star is Born (1954)
3. "Carioca" - Flying Down to Rio (1934)
4. "Boogie Woogie Bugle Boy of Company B" - Buck Privates (1941)
5. "Wild is the Wind" - Wild is the Wind (1957) 
6. "(Love is) The Tender Trap" - The Tender Trap (1955) 
7. "Pass That Peace Pipe" - Good News (1947)
8. "They're Either Too Young Or Too Old" - Thank Your Lucky Stars (1943)
9. "Cheek to Cheek" - Top Hat (1935)
10. "I've Got a Gal in Kalamazoo" - Orchestra Wives (1942)
11. "The Trolley Song" - Meet Me in St. Louis (1944)
12. "Ac-Cent-U-Ate the Positive" - Here Comes the Wave (1945)
13. "Zing a Little Zong"  - Just For You (1952)
14. "Almost in Your Arms (Love Song from Houseboat)" - Houseboat (1958)
15. "Build Me a Kiss to Dream On" - The Strip (1951)
16. "Wilhemina" - Wabash Avenue (1950)
17. "Through a Long and Sleepless Night" - Come to the Stable (1949)
18. "Waltzing in the Clouds" - Spring Parade (1940)
19. "Strange Are the Ways of Love" - The Young Land (1959)
20. "Ole Buttermilk Sky" - Canyon Passage (1946)
21. "Julie" - Julie (1956)
22. "Dust" - Under Western Stars (1938)
23. "The Woody Woodpecker Song" - Wet Blanket Policy (1948)
24. "I Poured My Heart Into a Song" - Second Fiddle (1939)
25. "Remember Me" - Mr. Dodd Takes the Air (1937)
26. "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. "Whatever Will Be, Will Be (Que Sera, Sera)" - The Man Who Knew Too Much (1956)
5. "All the Way" - The Joker is Wild (1957)
6. "Baby, It's Cold Outside" - Neptune's Daughter (1949)
7. "In the Cool, Cool, Cool of the Evening" - Here Comes the Groom (1951)
8. "Three Coins in the Fountain" - Three Coins in the Fountain (1954)
9. "High Noon (Do Not Forsake Me, Oh My Darlin')" - High Noon (1952)
10. "Love is A Many Splendored Thing" - Love is a Many Splendored Thing (1955)
11. "It Might as Well Be Spring" - State Fair (1945)
12. "White Christmas" - Holiday Inn (1942)
13. "Thanks for the Memory" - The Big Broadcast of 1938 (1938)
14. "The Last Time I Saw Paris" - Lady Be Good (1941)
15. "High Hopes" - A Hole in the Head (1959)
16. "Gigi" - Gigi (1958)
17. "Mona Lisa" - Captain Carey, U.S.A. (1950)
18. "Buttons and Bows" - The Paleface (1948)
19. "Zip-A-Dee-Doo-Dah" - Song of the South (1947)
20. "When You Wish Upon a Star" - Pinocchio (1940)
21. "Secret Love" - Calamity Jane (1953)
22. "You'll Never Know" - Hello, Frisco, Hello (1943)
23. "On the Atchinson, Topeka and Santa Fe" - Harvey Girls (1946)
24. "The Continental" - The Gay Divorcee (1934)
25. "The Lullaby of Broadway" - Gold Diggers of 1935 (1935)
26. "Sweet Leiulani" - Waikiki Wedding (1937)