Best Song: "Raindrops Keep Fallin' on My Head" (1969)

Scene from Butch Cassidy and the Sundance Kid

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 1969 and The Academy is celebrating its 42nd year. Director John Schlesinger's Midnight Cowboy became the first and only film in history to win Best Picture while sporting an X-Rating. It was the first ceremony to be broadcast internationally and is also considered by Nielsen Ratings to be the highest viewed. This was also the first year that every acting nomination was from a film that was shot in color. However, this was also one of the only years while all four acting winners did not appear in a Best Picture winner. Meanwhile, Butch Cassidy and the Sundance Kid kept the Best Original Song lively with the winning number "Raindrops Keep Falling on My Head."

The Nominees

Song: "Come Saturday Morning"

Film: The Sterile Cuckoo

Performers: The Sandpipers

It's so interesting how this decade has progressed. We started with Henry Mancini-esque happy songs with jaunty melodies. Now we're seeing more contemporary (for its time) approaches with folksy tunes with beautiful melodies. Maybe it's just because it feels different from most of what I have heard (or that I generally like this form of 60's music), but it definitely has a great feel to it. I like the melody and the vocals feel soothing. As a whole, this is just a great song that I likely wouldn't have ever guessed was nominated for Best Original Song by how accessible to radio it feels. While not one of the most engaging songs stylistically, it definitely is a welcomed alternative to what I've been hearing most of this decade.

Song: "Jean"

Film: The Prime of Miss Jean Brodie

Performers: Rod McKuen

I have to admit that I like the direction that the nominees are going in this year. While I still like The Sandpipers' song better, I think that Rod McKuen is great at understated impact. His voice feels like a whisper, and the production slowly builds up emotion in ways that hit you. What's more brilliant is that it's buried under an otherwise simplistic melody that doesn't draw attention to itself. It's a beautiful song that sways from note to note while gently rocking the listener deeper and deeper into the sentiment. I think that it's a little too monotonous, but it's also not without its charm. A solid entry that gives me hope for the folksier songs to come.

Song: "True Grit"

Film: True Grit

Performers: Glen Campbell

Well, this is proving to be a really good year for songs. In general, I think that the lyrics are probably the strongest point. It also helps that unlike the others on here, I have seen this film and recognize how they relate to the film. There's a certain poignancy to it that feels timely and emotional. I even like how the music compliments the lyrics with a little bit of a sentimental twang. I will admit that compared to the others, it does run a little long towards the end, but it's still a beautiful song about a generally intriguing and different thing from most other entries on here. I like it, though it's probably the least catchy of the ones on here - which may or may not impact its chances of winning Best Loser this week. Still, we're three for three, and I'm so excited about that.

Song: "What Are You Doing the Rest of Your Life"

Film: The Happy Ending

Performers: Michael Dees

Don't take this the wrong way, but this is my least favorite of the group. I will admit that one of the benefits is that all of these songs sound similar enough in a genre that I generally like. So to call this the worst isn't an insult, but just that I prefer what it does better in other songs. The whispering vocals are nice, and I like the understated melody. I think that lyrically, it is among the stronger entries. I just think that there's something a little too understated about it to keep me from fully enjoying it. The song has its moments and I like what it is going for. I just don't think it's able to fully achieve them with what's given. A good song, but definitely pales in comparison to the other entries on here.

The Winner

Song: "Raindrops Keep Fallin' on My Head"

Film: Butch Cassidy and the Sundance Kid

Performers: B.J. Thomas

It's so tough to say anything bad about this song. It's a great one from a great movie. While I try not to let that bias keep me from voting certain songs too high, it's impossible to not immediately see the magic of this song. With the strumming melody and the horns that come in, this is just iconic music from the era, beyond just winning an Oscar. The fact of the matter is that you could loop it for a few more rounds, and it'll still be as endearing. I also think that B.J. Thomas' strained voice adds a little optimism to the song, even if by accident. It's a great song and one that perfectly summarizes the appeal of being happy when nothing else is going right.

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. "The Green Leaves of Summer" - The Alamo (1960)
2. "That's Amore" - The Caddy (1953)
3. "A Town Without Pity" - A Town Without Pity (1961)
4. "The Man That Got Away" - A Star is Born (1954)
5. "The Sweetheart Tree" - The Great Race (1965)
6. "Carioca" - Flying Down to Rio (1934)
7. "Boogie Woogie Bugle Boy of Company B" - Buck Privates (1941)
8. "Charade" - Charade (1963)
9. "Wild is the Wind" - Wild is the Wind (1957) 
10. "(Love is) The Tender Trap" - The Tender Trap (1955) 
11. "Pass That Peace Pipe" - Good News (1947)
12. "They're Either Too Young Or Too Old" - Thank Your Lucky Stars (1943)
13. "Cheek to Cheek" - Top Hat (1935)
14. "I've Got a Gal in Kalamazoo" - Orchestra Wives (1942)
15. "Gegorgy Girl" - Georgy Girl (1966)
16. "The Trolley Song" - Meet Me in St. Louis (1944)
17. "Ac-Cent-U-Ate the Positive" - Here Comes the Wave (1945)
18. "Come Saturday Morning" - The Sterile Cuckoo (1969)
19. "Thoroughly Modern Millie" - Thoroughly Modern Millie (1967)
20. "Where Love Has Gone" - Where Love Has Gone (1964)
21. "Zing a Little Zong"  - Just For You (1952)
22. "Walk on the Wild Side" - Walk on the Wild Side (1962)
23. "Almost in Your Arms (Love Song from Houseboat)" - Houseboat (1958)
24. "Build Me a Kiss to Dream On" - The Strip (1951)
25. "Star!" - Star! (1968)
26. "Wilhemina" - Wabash Avenue (1950)
27. "Through a Long and Sleepless Night" - Come to the Stable (1949)
28. "Waltzing in the Clouds" - Spring Parade (1940)
29. "Strange Are the Ways of Love" - The Young Land (1959)
30. "Ole Buttermilk Sky" - Canyon Passage (1946)
31. "Julie" - Julie (1956)
32. "Dust" - Under Western Stars (1938)
33. "The Woody Woodpecker Song" - Wet Blanket Policy (1948)
34. "I Poured My Heart Into a Song" - Second Fiddle (1939)
35. "Remember Me" - Mr. Dodd Takes the Air (1937)
36. "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. "Moon River" - Breakfast at Tiffany's (1961)
2. "Somewhere Over the Rainbow" - The Wizard of Oz (1939)
3. "The Way You Look Tonight" - Swing Time (1936)
4. "Raindrops Keep Fallin' on My Head" - Butch Cassidy and the Sundance Kid (1969)
5. "Swinging on a Star" - Going My Way (1944)
6. "Whatever Will Be, Will Be (Que Sera, Sera)" - The Man Who Knew Too Much (1956)
7. "All the Way" - The Joker is Wild (1957)
8. "Never on Sunday" - Never on Sunday (1960)
9. "Chim Chim Cher-ee" - Mary Poppins (1964)
10. "Talk to the Animals" - Dr. Dolittle (1967)
11. "Baby, It's Cold Outside" - Neptune's Daughter (1949)
12. "In the Cool, Cool, Cool of the Evening" - Here Comes the Groom (1951)
13. "Born Free" - Born Free (1966)
14. "Three Coins in the Fountain" - Three Coins in the Fountain (1954)
15. "High Noon (Do Not Forsake Me, Oh My Darlin')" - High Noon (1952)
16. "Love is A Many Splendored Thing" - Love is a Many Splendored Thing (1955)
17. "It Might as Well Be Spring" - State Fair (1945)
18. "White Christmas" - Holiday Inn (1942)
19. "Thanks for the Memory" - The Big Broadcast of 1938 (1938)
20. "The Last Time I Saw Paris" - Lady Be Good (1941)
21. "High Hopes" - A Hole in the Head (1959)
22. "Gigi" - Gigi (1958)
23. "Mona Lisa" - Captain Carey, U.S.A. (1950)
24. "The Days of Wine and Roses" - The Days of Wine and Roses (1962)
25. "The Shadow of Your Heart" - The Sandpiper (1965)
26. "Buttons and Bows" - The Paleface (1948)
27. "Zip-A-Dee-Doo-Dah" - Song of the South (1947)
28. "When You Wish Upon a Star" - Pinocchio (1940)
29. "The Windmills of Your Mind" - The Thomas Crown Affair (1968)
30. "Secret Love" - Calamity Jane (1953)
31. "Call Me Irresponsible" - Papa's Delicate Condition (1963)
32. "You'll Never Know" - Hello, Frisco, Hello (1943)
33. "On the Atchinson, Topeka and Santa Fe" - Harvey Girls (1946)
34. "The Continental" - The Gay Divorcee (1934)
35. "The Lullaby of Broadway" - Gold Diggers of 1935 (1935)
36. "Sweet Leiulani" - Waikiki Wedding (1937)