Oscar-Winning Singer-Actors Trivia Quiz

Answer: Bing Crosby

Crosby is the prototypical singer-actor, considered a superstar in both roles. In addition to delivering an Oscar-winning performance in "Going My Way", Crosby also introduced "Swinging on a Star" in the film, which won an Oscar for Best Original Song and spent nine weeks as a number one hit for him.

As an actor, Crosby starred in both dramas and comedies (especially with Bob Hope); as a singer, he was praised by fans from Thelonious Monk to David Bowie. And he also started and sponsored a legendary golf tournament, now known as the AT&T Pebble Beach National Pro-Am.

Answer: Barbra Streisand

Before the 1968 movie of "Funny Girl", which was her movie debut, Streisand had starred in the 1964 Broadway play of it, and its feature song "People" became her signature song and first Billboard Top Ten hit. For "Evergreen", Streisand wrote the music and Paul Williams wrote the lyrics.

In addition to her acting, composing, and singing, Streisand won a Golden Globe Award for Best Director for the 1983 movie "Yentl", in which she also starred, co-wrote the screenplay, and sang (but didn't write any songs).

Answer: Burl Ives

Ives's singing career dated back to the 1930s, and he became a movie (and later TV) actor shortly after becoming a folk singing superstar with 1948's "Blue-Tail Fly". His best-known acting role was Big Daddy in "Cat on a Hot Tin Roof", with Paul Newman and Elizabeth Taylor, but his Christmas hit came from his voice role as narrator of the 1964 TV special "Rudolph the Red-Nosed Reindeer".

Answer: Cher

Cher and her first husband Sonny Bono hosted a successful variety show, "The Sonny and Cher Comedy Hour", on CBS-TV from 1971 until their divorce in 1974. Bob Mackie was already a well-known costume designer when he began dressing Cher for the show, but his star continued to rise along with hers.

By the end of that series, Cher had already recorded four Billboard number one hits (including one with Sonny) and a number two.

Answer: Frank Sinatra

Sinatra's 1953 Oscar and his simultaneous move to Capitol Records began the most productive part of his recording career, which ultimately led him to start his own record label, Reprise Records. He introduced one of his many big hits, the Oscar-winning Best Original Song "High Hopes", in a 1960 movie in which he starred, "A Hole in the Head".

As an actor, Sinatra usually played a character who didn't get pushed around. In fact, he was the original choice to play the hard-nosed cop in the movie "Dirty Harry" but had to withdraw due to a physical problem - which led the producers to make the lead character younger and cast Clint Eastwood in what became his signature role.

Answer: Prince

The soundtrack to "Purple Rain" included three major hits for Prince and the Revolution: two Billboard number one singles ("When Doves Cry" and "Let's Go Crazy") and a number two ("Purple Rain"). Prince then starred in two more movies, "Under the Cherry Moon" and "Graffiti Bridge" (which he also directed), both of which were nominated for Razzie Awards as the worst movie of the year, before he retreated back to music.

Answer: Paul McCartney

Before "Let It Be", Paul McCartney and The Beatles had filmed three theatrical films: "A Hard Day's Night", "Help!", and "Magical Mystery Tour" (which was originally intended as a British TV movie, and for which McCartney served as de facto director).

Another ex-Beatle, Ringo Starr, also became an actor after The Beatles broke up, most famously starring in "The Magic Christian" with Peter Sellers, who had been one of the group's heroes. Linda McCartney, Ringo, and Ringo's wife Barbara Bach all co-starred in "Give My Regards to Broad Street", along with Beatles producer George Martin and engineer Geoff Emerick (appropriately playing a record producer and engineer).

But after the savagely negative reception to this film, Paul McCartney did not take on another straight acting role until 2017's "Pirates of the Caribbean: Dead Men Tell No Tales".

Answer: Lady Gaga

At the time, Lady Gaga has only three dramatic performances to her credit, but she won a Golden Globe Award for Best Actress - Miniseries or Television Film for her second (in FX's "American Horror Story: Hotel"), and then was nominated for an Academy Award for "A Star Is Born", her third.

In late 2019, she announced plans for her fourth acting role (in a film directed by Ridley Scott), as well as her sixth studio album.

Answer: Keith Carradine

Director Robert Altman cast "Nashville" with many musicians who were only part-time actors in featured roles. Carradine, part of the Carradine family of actors that included his father John and his brothers David and Robert, was included because he was a talented musician as well as a full-time actor.

He brought his song "I'm Easy" to Altman and proposed that his character perform it in the movie, and Altman agreed. The soundtrack version of the song quickly skyrocketed into the Billboard Top 20 (and reached number one on the Billboard easy-listening charts) as well as winning the Oscar.

As a result, Carradine signed a contract with Asylum Records and recorded two albums of original songs before his successful acting career led him to lose interest in recording.

Answer: Bob Dylan

Sam Peckinpah, the director of "Pat Garrett and Billy the Kid", didn't like either Dylan (who played the enigmatic Alias in the movie) or "Knockin' on Heaven's Door" and complained that the studio forced him to include Dylan and the song in the movie - even though Dylan's co-star Kris Kristofferson, a fine singer-actor in his own right, called the song "the strongest use of music that I had ever seen in a film". Peckinpah's complaints may have been a reason that neither the song nor the score was nominated for an Academy Award, although Dylan's score was nominated for a British BAFTA Award. Since then, Dylan has taken on only a few more acting roles, including 1978's "Renaldo and Clara", which Dylan also co-wrote and directed, 1987's "Hearts of Fire", and 2003's "Masked and Anonymous" - but his 2016 Nobel Prize for literature is an indication that he probably made the right choice.