1959 Best Original Song - The One Where I Finally Pick a Sinatra Song

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WON AND SHOULD'VE WON: "High Hopes," A Hole in the Head

Over the past 25 years of Best Original Song I've thus far tackled, I have encountered half a dozen nominees performed by the incomparable Frank Sinatra - 1958's "To Love and Be Loved," 1957's Oscar-winning "All the Way," 1955's "(Love Is) The Tender Trap," 1954's "Three Coins in the Fountain," 1945's "I Fall in Love too Easily" and 1944's "I Couldn't Sleep a Wink Last Night."

All of those are pretty terrific tunes, yet, mostly on account of superior competition, I haven't yet selected a Sinatra-performed song as my favorite of an Original Song line-up.

At last, that changes with 1959 and the Academy's pick for Best Original Song, the irresistibly charming "High Hopes," which Sinatra performs alongside child actor Eddie Hodges in Frank Capra's immensely underrated A Hole in the Head. The tune, which was later selected by John F. Kennedy to serve as the theme to his successful 1960 presidential campaign, is such a joy to listen to, catchy as can be, particularly with the adorable Hodges in the mix (Sinatra of course later did a solo version too, which admittedly isn't quite as fun). When I eventually hang up my hat in reviewing this category, I wholly expect "High Hopes" to rank awfully high on my ranked list of the winners (I have it at #3 for now).

As for the rest of the line-up, it's not a whole lot to write home about, though I've certainly encountered far worse in this category.

I like both Johnny Mathis' "The Best of Everything," from the Peyton Place-wannabe of the same name (which isn't terribly notable beyond a great late supporting turn by Joan Crawford), and Marty Robbins' "The Hanging Tree," from the fine Karl Malden-Gary Cooper western of the same name. In another, weaker year, I could perhaps see one of these two emerging as a contender for the win, but they ain't "High Hopes."

Danny Kaye's "The Five Pennies" is a pleasant but very slight lullaby, written by wife/composer Sylvia Fine. The fifth nominee, "Strange Are the Ways of Love," from the Patrick Wayne (John's son) vehicle The Young Land, is simply wretched, even though it's from the same brilliant team that produced the great theme from High Noon, which I actually picked for the win in its year.

The Oscar-winners ranked (thus far)...

  1. "Over the Rainbow," The Wizard of Oz (1939)
  2. "The Way You Look Tonight," Swing Time (1936)
  3. "High Hopes," A Hole in the Head (1959)
  4. "Whatever Will Be, Will Be (Que Sera, Sera)," The Man Who Knew Too Much (1956)
  5. "Mona Lisa," Captain Carey, U.S.A. (1950)
  6. "You'll Never Know," Hello, Frisco, Hello (1943)
  7. "On the Atchison, Topeka and the Santa Fe," The Harvey Girls (1946)
  8. "Baby, It's Cold Outside," Neptune's Daughter (1949)
  9. "High Noon (Do Not Forsake Me, On My Darlin')," High Noon (1952)
  10. "Secret Love," Calamity Jane (1953)
  11. "White Christmas," Holiday Inn (1942)
  12. "When You Wish Upon a Star," Pinocchio (1940)
  13. "Thanks for the Memory," The Big Broadcast of 1938 (1938)
  14. "Lullaby of Broadway," Gold Diggers of 1935 (1935)
  15. "Zip-a-Dee-Doo-Dah," Song of the South (1947)
  16. "All the Way," The Joker Is Wild (1957)
  17. "It Might As Well Be Spring," State Fair (1945)
  18. "The Last Time I Saw Paris," Lady Be Good (1941)
  19. "In the Cool, Cool, Cool of the Evening," Here Comes the Groom (1951)
  20. "Love Is a Many-Splendored Thing," Love Is a Many-Splendored Thing (1955)
  21. "Three Coins in the Fountain," Three Coins in the Fountain (1954)
  22. "Swinging on a Star," Going My Way (1944)
  23. "Gigi," Gigi (1958)
  24. "The Continental," The Gay Divorcee (1934)
  25. "Sweet Leilani," Waikiki Wedding (1937)
  26. "Buttons and Bows," The Paleface (1948)