Earl Thomas Conley
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40 free Earl Thomas Conley trivia questions with answers — music quiz, new questions added Oct 2026.
Earl Thomas Conley was one of the most dependable hitmakers in 1980s country music, a songwriter first and a star second, whose records were often called thinking man's country for the way they dwelt on doubt, temptation and regret. 'What I'd Say', his 1988 single about a man practising a speech he may never get to give, is the song many listeners still search for by name. This quiz covers the full career: the long apprenticeship writing for other singers, the streak of chart-toppers, the duets that crossed genre lines, the songwriters and producers behind the records, and the covers and tributes that followed. Several questions look closely at 'What I'd Say' itself, from its story to the artists who later recorded it. It is written for fans of classic country radio. The early questions stick to the big songs and famous names, and the later ones are for listeners who know the album tracks and the liner notes.
30 of 40 questions with answers and explanations. Play the quiz
Q 01Earl Thomas Conley's 1986 R&B duet earned him a rare country booking on which syndicated dance show?
Soul Train
Soul Train had Conley on to sing his crossover duet, and he is widely cited as the only country artist ever to appear on the show.
Q 02Which country star, co-writer of 'All Over Me' with Earl Thomas Conley, called him his all-time favorite singer?
Blake Shelton
Blake Shelton broke the news of Conley's death in 2019, calling him his hero and friend. Their song, written with Michael Pyle, was a top twenty country hit for Shelton in 2002.
Q 03In Earl Thomas Conley's 'What I'd Say', the narrator rehearses imaginary conversations with which absent person?
The woman who left him
The woman who left him never hears the speech: the song ends with her having to wait until they meet to find out. It became Conley's seventeenth country number one.
Q 04Which Eagles member first recorded the song Earl Thomas Conley released in 1989 as 'You Must Not Be Drinking Enough'?
Don Henley
Don Henley cut it in 1984 as 'You're Not Drinking Enough' on his solo album Building the Perfect Beast, with soul singer Sam Moore on harmony.
Q 05Which Dukes of Hazzard actor co-wrote Earl Thomas Conley's 1991 top ten country single 'Shadow of a Doubt'?
Tom Wopat
Tom Wopat, who played Luke Duke, wrote it with Robert Byrne and released a string of country singles of his own. Conley's recording reached number eight.
Q 06Earl Thomas Conley's 1991 duet 'Brotherly Love' stalled at number two behind 'Shameless', a hit for which superstar?
Garth Brooks
Garth Brooks held the top spot with his cover of a Billy Joel song from Ropin' the Wind. The duet became the last top ten hit for both of its singers.
Q 07Which singer joined Earl Thomas Conley on the 1988 number one duet 'We Believe in Happy Endings'?
Emmylou Harris
Emmylou Harris scored her final country number one with the duet, and the pair earned a Grammy nomination for Best Country Collaboration with Vocals.
Q 08Earl Thomas Conley's 1986 crossover duet partner Anita sang with which Grammy-winning family group from Oakland?
The Pointer Sisters
The Pointer Sisters won their first Grammy for a country song, 'Fairytale', which Anita co-wrote, and were the first Black female group to perform at the Grand Ole Opry.
Q 09Only Ronnie Milsap and which band scored more number one country singles in the 1980s than Earl Thomas Conley?
Alabama
Alabama and Milsap were the only acts ahead of him: Conley's 18 chart-toppers were the third most by any artist in any genre that decade.
Q 10Which country star took the Earl Thomas Conley song 'This Time I've Hurt Her More Than She Loves Me' to number one?
Conway Twitty
Conway Twitty topped the chart with it in 1975, years before Conley had a hit of his own. Conley later recorded the song himself.
Q 11Which Kentucky-born singer, who died in 1989, is heard with Earl Thomas Conley on the duet 'Brotherly Love'?
Keith Whitley
Keith Whitley and Conley recorded it in 1987, but it sat unreleased until 1991, when it appeared on albums by both men and earned a Grammy nomination.
Q 12Earl Thomas Conley's 'What I'd Say' topped the country chart in the United States and which other nation?
Canada
Canada's RPM country chart also put the single on top. In the US it was the third single from its album and spent fourteen weeks on the chart.
Q 13Which branch of the US military did Earl Thomas Conley join after turning down a scholarship?
The Army
Q 21Which country singer covered Earl Thomas Conley's 'What I'd Say' on her 2016 album Letting Go...Slow?
Lorrie Morgan
Lorrie Morgan set it beside songs by Patsy Cline, Bobbie Gentry and Bob Dylan on an album that mixed covers with new material.
Q 22Which guitarist and producer, son of a bluegrass banjo legend, co-wrote Earl Thomas Conley's 'Chance of Lovin' You'?
Randy Scruggs
Randy Scruggs, son of Earl Scruggs, shared the writing on five of Conley's number ones, starting with 'Your Love's on the Line' in 1983.
Q 23Which Thom Schuyler song gave Earl Thomas Conley his eighteenth and final country number one in 1989?
Love Out Loud
The Army is where Conley's singing talent first showed, and after his discharge he began commuting to Nashville to chase a music career.
Q 14Which major label released seven of Earl Thomas Conley's ten studio albums, ending with 1991's Yours Truly?
RCA Records
RCA Records signed Conley once his independent single had hit number one, then dropped him in 1992 as his sales fell.
Q 15Before enlisting, Earl Thomas Conley turned down a scholarship to study which subject?
Art
Art was his first talent: an older sister encouraged his drawing, and in later life he painted his two daughters on a jewelry box he made as a gift.
Q 16What style of music did Earl Thomas Conley sing in a trio with his aunt and uncle before chasing country stardom?
Gospel
Gospel gave Conley his first stage: the family trio made its debut at the Palace Theater in his Ohio hometown.
Q 17Which 1983 Earl Thomas Conley number one, written by Walt Aldridge and Tom Brasfield, earned him a Grammy nomination?
Holding Her and Loving You
Holding Her and Loving You became one of Conley's best-known songs, and Clay Walker put a live version of it back on the country chart in 1998.
Q 18Which Ohio River city, the birthplace of Earl Thomas Conley, has a riverside park nearby named in his honor?
Portsmouth
Portsmouth was a steelworking town when Conley was born there in 1941, and he later put in a spell at a steel mill himself before music paid.
Q 19Which self-written single became Earl Thomas Conley's first country number one in the summer of 1981?
Fire and Smoke
Fire and Smoke reached the top in July 1981 on a small independent label, and the major-label deal that followed produced seventeen more chart-toppers.
Q 20Which California country singer covered Earl Thomas Conley's 'What I'd Say' on the 2001 album Alright Guy?
Gary Allan
Gary Allan put it on the platinum-selling album that also gave him 'Man to Man', his first number one.
Love Out Loud closed a run that began in 1981. Its follow-up single stalled at number 26, and Conley never topped the chart again.
Q 24In which nation was Earl Thomas Conley stationed for two years when country music first caught his interest?
West Germany
West Germany hosted him for two years of service. Back home in Ohio, he started making regular trips to Nashville to pitch his songs.
Q 25Robert Byrne, co-writer of Earl Thomas Conley's 'What I'd Say', worked mainly at FAME Studios in which music town?
Muscle Shoals
Muscle Shoals writer Byrne supplied four of Conley's number ones, and he later co-produced the band Shenandoah's records with FAME founder Rick Hall.
Q 26Earl Thomas Conley left home at 14 after his father lost a job in which industry?
The railroad
The railroad laid his father off as steam engines were phased out, and the teenager was taken in by his older sister Joyce in another Ohio town.
Q 27Which 1988 Earl Thomas Conley album produced four number one singles, including 'What I'd Say'?
The Heart of It All
The Heart of It All sent four straight singles to the top, with 'What I'd Say' the third of them, released in October 1988.
Q 28Earl Thomas Conley's record of four number one singles from one album fell to Diamonds & Dirt, by which singer?
Rodney Crowell
Rodney Crowell sent all five singles from his 1988 album to the top. Conley had set the mark with Don't Make It Easy for Me in 1984.
Q 29Which 1984 single became the record fourth number one from Earl Thomas Conley's album Don't Make It Easy for Me?
Angel in Disguise
Angel in Disguise came with a David Hogan video in which Conley daydreams about a string of glamorous women, who then turn up to visit him.
Q 30In which Southern city did Earl Thomas Conley settle after leaving Nashville, and meet the producer who signed him?
Huntsville
Huntsville, the Rocket City, is where he met the producer who took him to GRT Records in 1974, though none of his four singles there became hits.