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60 free Oldies Music trivia questions with answers — music quiz, new questions added Aug 2026.
Oldies radio has a fairly precise meaning: the pop, rock and roll, doo-wop, soul and surf music of roughly 1955 to 1969, the records that KOOL-FM in Phoenix and a wave of imitators built a format around in the early 1970s. This quiz sticks to that golden window and to the songs that still get played, from Rock Around the Clock to Sugar, Sugar. The 58 oldies music trivia questions here go beyond naming the artist. You will be asked why the FBI spent 31 months listening to Louie Louie, which single hit number one twice in separate chart runs, who gave up his seat on Buddy Holly's plane, what Phil Spector printed on a record label to fool disc jockeys, how much Motown was started with, and which cartoon band had the biggest hit of 1969. Easy questions come first; the back half is for people who know their B-sides. No lyrics are quoted, so nothing here will get you humming the answer. Every fact is checked against the Wikipedia article for that song, artist or event, and the sentence that establishes it is shown under each question.
30 of 60 questions with answers and explanations. Play the quiz
Q 01Which decades does the term 'oldies' most specifically cover in radio programming?
The mid-1950s to the late 1960s
Since 2000 many stations have crept into the 1970s, and 'classic hits' has taken over the 1980s end.
Q 02Which Phoenix station is credited as one of the first to adopt an oldies format in the early 1970s?
KOOL-FM
The timing was no accident: nostalgia for the 1950s was booming in the early 70s.
Q 03Which 1973 film is often credited with kick-starting the 1950s nostalgia boom that fueled oldies radio?
American Graffiti
George Lucas's soundtrack of 41 oldies became a bestselling double album, and Happy Days followed on TV a year later.
Q 04When did 'Rock Around the Clock' become the first rock and roll record to top the pop chart?
July 9, 1955
It stayed there for eight weeks, a year after flopping as the B-side of 'Thirteen Women (and Only One Man in Town)'.
Q 05Which 1955 film's opening credits turned 'Rock Around the Clock' into a hit a year after its release?
Blackboard Jungle
The Bill Haley & His Comets recording is often cited as the biggest-selling vinyl rock single ever, at 25 million or more.
Q 06'Rock Around the Clock' opened which 1970s sitcom during its first two seasons?
Happy Days
The show later switched to its own 'Happy Days' theme, which became a hit in its own right in 1976.
Q 07In which Mississippi town was Elvis Presley born in 1935?
Tupelo
His twin brother Jesse Garon was stillborn 35 minutes before him.
Q 08How many Grammy Awards did Elvis Presley win in his lifetime?
Three
All three were for gospel recordings, not for any of his rock and roll hits.
Q 09How many rooms does Graceland, the mansion Elvis bought in March 1957, have?
18
He was 22 and paid about $100,000; he died there in August 1977 at 42.
Q 10What does Wikipedia say actually happened when Elvis was supposedly filmed waist-up on Ed Sullivan?
He was shown head-to-toe
The waist-up framing came only on his third Sullivan appearance in January 1957, after the first two had shown everything.
Q 11On what date did the plane carrying Buddy Holly, Ritchie Valens and the Big Bopper crash?
February 3, 1959
They had just played the Surf Ballroom on the Winter Dance Party tour; the ballroom still holds a memorial concert every year.
Q 12Which future country star gave up his seat on that plane to the Big Bopper, who was ill?
Waylon Jennings
Jennings was Holly's bass player on the tour and was haunted by a joking exchange the two had about the flight.
Q 13Ritchie Valens got his seat on the plane by winning what?
A coin toss with guitarist Tommy Allsup
Q 21Who wrote 'The Twist' after watching teenagers in Tampa do the dance?
Hank Ballard
Ballard and the Midnighters buried it as a B-side in 1958; a young Philadelphia singer's copy became the phenomenon.
Q 22Chubby Checker's 'The Twist' was the first record ever to do what?
Hit number one in two separate runs on the chart
It topped the Hot 100 in September 1960 and again in January 1962, once adults had caught on to the dance.
Q 23'Louie Louie' was written, composed and first recorded by which musician in 1956?
Richard Berry
Valens was afraid of flying and was 17 years old; Allsup later opened a club called the Heads Up Saloon.
Q 14Which 1971 song coined the phrase 'The Day the Music Died' for the crash?
'American Pie' by Don McLean
McLean was a 13-year-old paperboy when he read the news, and the song's eight and a half minutes turn the crash into a myth.
Q 15'La Bamba', Ritchie Valens' 1958 hit, is a folk song from which Mexican state?
Veracruz
It is a son jarocho tune, and Valens' version is the only non-English song on Rolling Stone's 500 Greatest Songs list.
Q 16Valens' 'La Bamba' was originally released as the B-side of which single?
'Donna'
'Donna' was the ballad written for his girlfriend; the flip side became the more famous song.
Q 17Which cover of 'La Bamba' reached number one on the Hot 100 in 1987?
Los Lobos
It was only the fourth entirely non-English song to top the Hot 100.
Q 18'Johnny B. Goode' is one of 27 pieces of music carried on what, launched in 1977?
The Voyager Golden Record
It sits alongside Bach and Beethoven as humanity's greeting to whoever finds the probe.
Q 19'Great Balls of Fire' was recorded by Jerry Lee Lewis on October 8, 1957 where?
Sun Studio in Memphis
It topped the country chart and the UK singles chart, though it stalled at number two on the US pop chart.
Q 20How many copies did 'Great Balls of Fire' sell in its first ten days of US release?
One million
Otis Blackwell, who wrote it with Jack Hammer, also wrote 'Don't Be Cruel' and 'All Shook Up' for Elvis.
The Kingsmen's famous 1963 recording came from a one-hour session that cost somewhere between $36 and $50.
Q 24How long did the FBI investigate the Kingsmen's 'Louie Louie' for supposedly obscene lyrics?
31 months
The Bureau's conclusion was that it could not make out a single word; Indiana's governor had already asked for a ban.
Q 25Who wrote and originally recorded 'Respect' in 1965, two years before Aretha Franklin's version?
Otis Redding
Franklin's rearrangement, with her sisters on backing vocals, spent two weeks at number one and won her two Grammys in 1968.
Q 26'(Sittin' On) The Dock of the Bay' was the first record to achieve what on the US chart?
A posthumous number one
Redding recorded it three days before dying in a plane crash on December 10, 1967, and never heard the finished mix.
Q 27Who co-wrote '(Sittin' On) The Dock of the Bay' with its singer?
Steve Cropper
Nobody is sure who performed the whistling at the end; Cropper has said Redding was improvising a verse he never finished.
Q 28'Be My Baby' was the 1963 debut single of which group on Philles Records?
The Ronettes
Ronnie Spector is the only Ronette actually on the record; the rest of the wall was session singers and the Wrecking Crew.
Q 29Which Beach Boy has called 'Be My Baby' the greatest pop record ever made?
Brian Wilson
Hal Blaine's opening drum figure, suggested by arranger Jack Nitzsche, has been copied on hundreds of records since.
Q 30'The Lion Sleeps Tonight' descends from 'Mbube', a 1939 song written by which South African musician?
Solomon Linda
Linda died poor in 1962; his family finally won a royalty settlement in the 2000s after the song's use in The Lion King.