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Quiz: Who sang the most Oscar-winning songs?

February 28, 2010 |  5:35 pm

Gold Derby reader Jeff Commings suggests this trivia quiz. Only one artist was the original singer on four Oscar-winning songs. Who? To see the answer, click the "Continue Reading" link below.

Oscars Trivia Quiz Academy Awards song news

ANSWER: f.) Bing Crosby sang four Oscar-winning songs: "Sweet Leilani" ("Waikiki Wedding," 1942), "White Christmas" ("Holiday Inn," 1944), "Swinging on a Star" ("Going My Way," 1951), "In the Cool, Cool, Cool of the Evening" ("Here Comes the Groom," 1938). Jennifer Warnes was the original singer on three Oscar-winning tunes: "It Goes Like It Goes" ("Norma Rae," 1979), "Up Where We Belong" ("An Officer and a Gentleman," 1982) and "(I've Had) The Time of My Life" ("Dirty Dancing," 1987). These thrushes sang two winners each: Irene Cara ("Fame" and "Flashdance ...What a Feeling"), Madonna ("Sooner or Later" and "You Must Love Me"), Barbra Streisand ("The Way We Were" and "Evergreen"), Judy Garland ("Over the Rainbow" and ""On the Atchison, Topeka and the Santa Fe"), Celine Dion ("Beauty and the Beast," "My Heart Will Go On"), Doris Day ("Que Sera Sera," "Secret Love") and Maureen McGovern ("There's Got to Be a Morning After," "We May Never Love Like This Again").

Photos: Judy Garland in "Wizard of Oz" (MGM), top left;  Barbra Streisand in "Funny Girl" (Columbia), top right.


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Barbra acutally sang four nominated songs: "I Finally Found Someone" and "Funny Girl"

Bob Hope didn't sing "Baby It's Cold Outside" (he wasn't even in that movie), but he did sing "Buttons and Bows" from "The Paleface", which was a winner.

Tom, you still forgot to add Bob Hope & Frank Sinatra. Also, Sinatra actually sang three BOS winners--his first was "Three Coins in the Fountain" (from the film of that name) in 1954. (Bing, of course, is still the all-time champ.)

As far as "Beauty and the Beast", the Celine Dion-Peabo Bryson version was sung over the end credits and included in the soundtrack album, so as far as I'm concerned it's co-official with the Angela Lansbury version. (I don't know where it fell in the end credits, but I don't think the "first song" rule was in place at that time.)

Speaking of which, Peabo Bryson is also a double-singer: In addition to "Beauty and the Beast", he also sang the pop version of "A Whole New World" from "Aladdin" (with Regina Belle--in-film version by Brad Kane & Lea Salonga).

In addition, Sally Dworsky co-sang the in-film versions of both "Can You Feel the Love Tonight" from "The Lion King" (with Kristle Edwards, Joseph Williams, Nathan Lane & Ernie Sabella--pop version by Elton John) and "When You Believe" from "The Prince of Egypt" (with Michelle Pfeiffer--pop version by Mariah Carey & Whitney Houston).

Finally, an exception: Fred Astaire isn't on this list because he did NOT sing along with Ginger Rogers on "The Continental" from "The Gay Divorcee", the first-ever BOS winner--though he did dance with Ginger *AND* later recorded his own version of "The Continental". Fred only sang "The Way You Look Tonight" from "Swing Time".

Wow. I was completely unaware of Bing's involvement in "Sweet Leilani" and "...Cool, Cool, Cool...," since I have only heard cover versions, and I could not find information on the original performer on either. I'm going to hunt down those films and watch ol' Bing sing.

Thanks, Dr. L. And thanks to everyone for adding more two-song performers to the list. I knew it was longer than the ones I originally suggested, but wasn't sure if Tom wanted to add them all to the list of choices.

And I don't count Celine as singing two winning songs. Angela Lansbury was the original performer on "Beauty and the Beast," just like Brad Kane and Lea Salonga were the original singers on "A Whole New World." I'd count Elton John as the original performer on "Can You Feel the Love Tonight" because the melody and lyrics are different, and his version is the one reportedly submitted for consideration.

Also, Maureen McGovern wasn't the original performer on "The Morning After." That was vocal double Renee Armand.

Thanks, Dr. L and par3182 -- you're right and I've changed text to reflect correct info.

Two more two timers -

Doris Day - "Que Sera Sera" (The Man Who Knew Too Much) and "Secret Love" (Calamity Jane)

Maureen McGovern - "There's Got To Be A Morning After" (The Poseidon Adventure) and "We May Never Love Like This Again" (The Towering Inferno)

Actually, I am pretty sure Bing Crosby sang four Oscar-winning songs

1937 "Sweet Leilani" from Waikiki Wedding -- Music and Lyrics by Harry Owens

1942 "White Christmas" from Holiday Inn -- Music and Lyrics by Irving Berlin

1944 "Swinging on a Star" from Going My Way -- Music by James Van Heusen; Lyrics by Johnny Burke

1951 "In the Cool, Cool, Cool of the Evening" from Here Comes the Groom -- Music by Hoagy Carmichael; Lyrics by Johnny Mercer

I also remember Bob Hope sang two

1938 "Thanks for the Memory" from The Big Broadcast of 1938 -- Music by Ralph Rainger; Lyrics by Leo Robin

1949 "Baby, It's Cold Outside" from Neptune's Daughter -- Music and Lyrics by Frank Loesser

Doris Day has two

1953 "Secret Love" from Calamity Jane -- Music by Sammy Fain; Lyrics by Paul Francis Webster

1956 "Whatever Will Be, Will Be (Que Sera, Sera)" from The Man Who Knew Too Much -- Music and Lyrics by Jay Livingston and Ray Evans

Frank Sinatra has two

1957 "All The Way" from The Joker Is Wild -- Music by James Van Heusen; Lyrics by Sammy Cahn

1959 "High Hopes" from A Hole in the Head -- Music by James Van Heusen; Lyrics by Sammy Cahn

Technically, didn't Angela Lansbury and not Celine Dion sing "Beauty and the Beast?" Celine had the hit (with Peabo Bryson) that was simultaneous with the film, but Lansbury's version was the one in the movie. Celine's might count as a cover.

YEs...but celine sang lots of oscar nominated songs...even I finally found someone and The Prayer

Bing Crosby sang,
Sweet Leilani
White Christmas
Swinging on a Star
In the Cool, Cool, Cool of the Evening.

Nice addition, Trebora! I've added it to the list. Thank you.

CĂ©line Dion also sang two Oscar winning songs. "Beauty and the Beast" & "My Heart Will Go On"



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