120+ Best Oldies Trivia Questions & Answers

Question: What year did The Lettermen first croon their way into hearts — way before Spotify playlists?

Answer: 1961

Question: Who was jazzin' it up with a trumpet and known to fans as “Pops”?

Answer: Louis Armstrong

Question: This musical legend was born when cars still needed cranking — what year did Louis Armstrong arrive?

Answer: 1901

Question: Which song did Frank Sinatra make so iconic, it basically became the national anthem of suave?

Answer: My Way

Question: Which Dean Martin hit sounds like it should play when your crush finally texts back?

Answer: You're Nobody till Somebody Loves You

Question: Before moonwalking, which future King of Pop debuted with “Got to Be There”?

Answer: Michael Jackson

Question: Which Godfather of Soul begged, pleaded, and please please pleased his way into music history in 1956?

Answer: James Brown

Question: What was the original name of The Supremes before they got, well... supremely famous?

Answer: The Primettes

Question: This singer’s heart belonged to Daddy — and no, it wasn’t a sugar baby anthem. Who was she?

Answer: Mary Martin

Question: In 1956, who belted “Anything Goes” before it became a musical theatre rite of passage?

Answer: Frank Sinatra

Question: Which singer turned "War! Huh! What is it good for?" into a protest anthem with power?

Answer: Edwin Starr

Question: Before TikTok charts, who scored the first-ever UK Number One single?

Answer: Al Martino

Question: Who gave us “A World Without Love” in 1964 — a hit that sounds like a sad rom-com title?

Answer: Peter and Gordon

Question: Which crooner made “Ain’t That a Kick in the Head” feel like a Vegas punchline?

Answer: Dean Martin

Question: This duo sang “Hey Paula” in 1962 — and no, it wasn’t about Abdul. Who were they?

Answer: Paul & Paula

Question: At what age do music legends like Hendrix, Joplin, and Cobain seem to clock out of life’s party?

Answer: 27

Question: Which shadowy figure guided Elvis’s rise with a title that sounds more military than musical?

Answer: Colonel Tom Parker

Question: Before fame hit, what simpler name did Smokey Robinson’s iconic Motown crew go by?

Answer: The Miracles

Question: Who gave us a soul anthem in 1961 that still plays during tearjerker movie moments and wedding vows?

Answer: Ben E King

Question: Which 1958 instrumental hit by The Champs makes you crave tacos and say the title out loud?

Answer: Tequila

Question: Whose smoky vocals made “I Heard It Through the Grapevine” sound like the juiciest secret ever sung?

Answer: Marvin Gaye

Question: Who delivered Spirit in the Sky in 1969 with fuzz guitars and a gospel twist—not your average hymn?

Answer: Norman Greenbaum

Question: Which cult classic film made “Stuck in the Middle with You” unforgettable… and a little unsettling?

Answer: Reservoir Dogs

Question: Which country gave us the powerhouse voice of Judy Garland—long before the yellow brick road?

Answer: USA

Question: In 1967, who sang a love song titled “Katherine”—a woman we still know nothing about?

Answer: Ben E King

Question: Which 1972 Aretha Franklin album turned identity, pride, and power into a bold musical statement?

Answer: Young, Gifted and Black

Question: Which 1958 novelty hit had drivers and DJs alike honking along to its onomatopoeic chorus?

Answer: The Playmates

Question: What year did Dean Martin leave Las Vegas behind for good, joining his Rat Pack brothers in the sky?

Answer: 1995

Question: Which band dropped a 1969 hit that blended jazz, rock, and soul into one wild sonic ride?

Answer: Blood, Sweat & Tears

Question: Which whimsical tune first appeared in a film filled with edible gardens, fizzy lifting drinks, and life lessons in song?

Answer: Willy Wonka & the Chocolate Factory

Question: Who sang about rainbows way before Kermit the Frog made it trendy in 1940?

Answer: Judy Garland

Question: Which legendary rock band put aside their epic feuds for one epic cause at Live 8?

Answer: Pink Floyd

Question: Before his velvet voice melted hearts, what instrument did Nat King Cole tickle with grace?

Answer: Piano

Question: Which band’s 1991 album Nevermind exploded grunge into the mainstream like a flannel-clad revolution?

Answer: Nirvana

Question: Whose heart went on and on (and on) to dominate 1997’s charts — and sink Titanic-level emotions?

Answer: Celine Dion

Question: Which group brought us “The Wah-Watusi” in 1962 — and no, it’s not a martial arts move?

Answer: The Orlons

Question: Who told us to Call Me — long before Blondie made it a hotline bling?

Answer: Aretha Franklin

Question: Who demanded Respect and told us to Think — making sass and soul a national treasure?

Answer: Aretha Franklin

Question: Which group served up a funky instrumental hit called “Green Onions” — no tears, just grooves?

Answer: Booker T. & the M.G.'s

Question: Which Monkee made hearts swoon before sadly passing in 2012? (Hint: Not the one with the wool hat!)

Answer: Davy Jones

Question: Who summoned “Mr. Sandman” in 1954 with harmonies so dreamy, insomniacs got jealous?

Answer: The Chordettes

Question: Which song sounds like a morning alarm clock with retro charm and teen angst?

Answer: Wake Up Little Susie

Question: Who made us feel all the feels with “I’ll Be There” in 1970 — the original boy band brotherhood?

Answer: Jackson 5

Question: Whose candle burned bright for Marilyn Monroe before it was relit for Princess Diana?

Answer: Elton John

Question: Which rock ‘n’ roll rebel said “That’s All Right” with a debut that started a hip-shaking revolution?

Answer: Elvis Presley

Question: Which U.S. state gave us the King of Rock 'n' Roll?

Answer: Mississippi

Question: Which 1992 hit made Whitney Houston the queen of breakup ballads?

Answer: I Will Always Love You

Question: Who wrote “Who Wants to Be a Millionaire?” before it was a game show?

Answer: Cole Porter

Question: Which Sinatra classic sounds perfect for a moonlit slow dance?

Answer: Moonlight in Vermont

Question: Who gave America its unofficial anthem with “God Bless America”?

Answer: Irving Berlin

Question: Which musical did Cole Porter turn into a Broadway hit with sass?

Answer: Kiss Me, Kate

Question: Which group made teens cry happy tears with “16 Candles”?

Answer: The Crests

Question: Who broke solo artist records in 2012 with the most #1 albums?

Answer: Madonna

Question: Which instrument did Louis Armstrong turn into pure magic?

Answer: Trumpet

Question: Who wrote “White Christmas,” the ultimate holiday jam?

Answer: Irving Berlin

Question: Who got us grooving with “Land of 1,000 Dances”?

Answer: Wilson Pickett

Question: Which 1993 album had Sinatra singing duets with stars?

Answer: Duets

Question: Who sang “You're The Top” way before it became a jazz night staple?

Answer: Paul Whiteman

Question: Who was Dylan's musical hero that pulled him to NYC?

Answer: Woody Guthrie

Question: Which iconic girl group started with Diana Ross and Mary Wilson?

Answer: The Supremes

Question: How many golden Grammys did Ella collect before Beyoncé made it cool?

Answer: 13

Question: Who wrote “Hallelujah I Love Her So” — the OG love jam before DMs?

Answer: Ray Charles

Question: Which instrument did Mort Shuman play when he wasn’t writing heartbreak bangers?

Answer: Piano

Question: Ella Fitzgerald’s voice could glide through how many octaves like butter on jazz?

Answer: Three

Question: Who won American Idol before reality TV had a filter?

Answer: Kelly Clarkson

Question: Who gathered the ladies and formed a group so fierce, even Destiny’s Child took notes?

Answer: Patti LaBelle

Question: Before Elvis made it a bop, who barked out the real “Hound Dog”?

Answer: Big Mama Thornton

Question: Who dropped “Heebie Jeebies” in 1926 — and accidentally invented scat singing?

Answer: Louis Armstrong

Question: Who sat on the dock, whistled a tune, and made soul history?

Answer: Otis Redding

Question: Whose heart didn’t belong to a boyband, but to herself — and a 1977 chart-topper?

Answer: Barbra Streisand

Question: When did Billie Holiday stun the world with “Strange Fruit” — a song that still shakes souls?

Answer: 1939

Question: Who made “You Make Me Feel So Young” sound like the soundtrack to a classy Sunday brunch?

Answer: Ella Fitzgerald

Question: What voice type did Nat King Cole use to melt hearts like butter on warm toast?

Answer: Baritone

Question: Where was Supremes star Cindy Birdsong born—hint: not Motown!?

Answer: New Jersey

Question: Who dropped the 1970 album Everything Is Everything with serious diva energy?

Answer: Diana Ross

Question: Which 1965 Ben E. King album had more soul than your dad’s playlist?

Answer: Seven Letters

Question: Elvis made Blue Christmas a hit in what year—just in time to ruin holiday cheer (in a good way)?

Answer: 1964

Question: Who grooved into 1969 with Rhythm of Life before Spotify was even a dream?

Answer: Sammy Davis, Jr.

Question: Which year did the jazzy classic Night and Day first charm its way into hearts?

Answer: 1932

Question: What year did Phil Harris unleash The Thing—and nope, it’s not a horror movie?

Answer: 1950

Question: When did The Famous Flames light up the soul scene for the first time?

Answer: 1953

Question: What year did Sinatra drop his final mic with his last album?

Answer: 1994

Question: When did My Way by Frank Sinatra become the anthem of dramatic exits?

Answer: 1969

Question: Which 13-year-old wowed the world in 1963 and later brought us Superstition?

Answer: Stevie Wonder

Question: When did Billie Holiday drop Strange Fruit—a song as powerful as it is poetic?

Answer: 1939

Question: Bill Haley rocked around the clock with which band?

Answer: Comets

Question: Who stepped into Diana Ross’s sparkly heels as lead of The Supremes in 1970?

Answer: Jean Terrell

Question: Which soulful powerhouse founded the Bluebelles girl group?

Answer: Patti LaBelle

Question: Which group of ladies backed Ray Charles with sass and soul?

Answer: The Raelettes

Question: Which punk band scored gold (finally!) in 1994 with a rebellious roar?

Answer: Bad Religion

Question: Which funky crew dropped Love Rollercoaster in 1975—hold on tight!?

Answer: Ohio Players

Question: In 2007, which band put their album on a USB—because why not be futuristic and loud?

Answer: The Mars Volta

Question: Which 1969 single by The Vogues sounds like a picnic in a meadow?

Answer: Green Fields

Question: Which band told you to Turn Around, Look at Me—and no, not in a creepy way?

Answer: The Vogues

Question: Which pop-punk band made Enema of the State weirdly iconic in 1999?

Answer: Blink-182

Question: Which band ruled the 2000s in sales—long after their mop-top days?

Answer: The Beatles

Question: Which show gave The Beatles their legendary U.S. TV debut?

Answer: Ed Sullivan

Question: Which “punk” group actually came straight outta Compton?

Answer: N.W.A.

Question: Who dropped the first British rock ‘n’ roll single—and made the UK shake?

Answer: Cliff Richard

Question: How many Gold Records did The Lettermen snag with their smooth harmonies?

Answer: 11

Question: Frank Sinatra didn’t just do it his way—he did it how many times in the studio?

Answer: 59

Question: Which vocal powerhouse broke records in 2008 with the most U.S. #1 hits as a solo act?

Answer: Mariah Carey

Question: What quirky title kicked off Barbra Streisand’s music career?

Answer: Miss Marmelstein

Question: Elvis’s first single that made fans scream before it even hit the charts?

Answer: That's All Right

Question: What was Elvis’s debut album called? (Spoiler: it’s not super original.)

Answer: Elvis Presley

Question: Who penned Lonely Avenue before Ray Charles made it soulful and sad?

Answer: Doc Pomus

Question: Which lyricist told us to Come Fly with Me—way before airlines charged for legroom?

Answer: Sammy Cahn

Question: Who wrote Respect before Aretha spelled it out loud and proud?

Answer: Otis Redding

Question: Who gave us the jazzy classic Who Wants to Be a Millionaire? long before game shows did?

Answer: Cole Porter

Question: Who belted I Get a Kick Out of You first—no auto-tune, all pipes?

Answer: Ethel Merman

Question: Who dreamed of a White Christmas and wrote the ultimate holiday banger?

Answer: Irving Berlin

Question: Who told us to Call Me—and no, it wasn’t Blondie this time?

Answer: Aretha Franklin

Question: Which legend gave us God Bless America—and every patriotic tear since?

Answer: Irving Berlin

Question: Who begged with Please, Please, Please in 1956—and meant every word?

Answer: James Brown

Question: Who wrote and sang Hallelujah I Love Her So—yes, he did it all?

Answer: Ray Charles