In March 1990, Doug Stone took his first steps into the country music world with the release of his self-titled debut album. His lead single, "I'd Be Better Off (In a Pine Box)," became a massive success, hitting the Top 5 on Billboard's Country Songs chart and positioning him as one of the most intriguing new artists of the decade.

Over the next few years, the Georgia native continued to build on that initial success with a string of hits, including eight No. 1 singles. In 1992, his career trajectory was almost derailed after illness caused him to cancel multiple shows and appearances. After doctors discovered numerous blockages in his heart, Stone underwent quadruple bypass surgery in Nashville. Thankfully, he was able to recover and released his third record, From the Heart, just a few months later.

Stone's love for country music started early — he began learning how to play the guitar at the age of five. He earned a slot opening for the late Loretta Lynn when he was just seven years old, a moment that only reinforced his drive to make country music the center of his life.

Let's take a look back at these 15 Doug Stone songs from the 1990s that showcase his incredible talents.

  • "In a Different Light"

    From: 'Doug Stone' (1990)

    Penned by Bob McDill, Dickey Lee and Bucky Jones, "In a Different Light" was released in 1991 as the final single from Stone's breakout self-titled debut. The wistful tale of an office romance also became the first No. 1 hit of his career.

  • "A Jukebox with a Country Song"

    From: 'I Thought It Was You' (1991)

    Stone's early career was marked by a rapid-fire release of impressive tracks, including his 1991 single "A Jukebox with a Country Song." In the tune, he retreats to an old honky-tonk for comfort after a lover's quarrel, only to find that his favorite hideaway has been transformed into something unexpected.

  • "Too Busy Being in Love"

    From: 'From the Heart' (1992)

    This sweet, charming love song from writers Victoria Shaw and Gary Burr became a No. 1 hit for Stone shortly after its release in late 1992.

    "I could have written a play so sweet and so funny / Given old Mr. Shakespeare a run for his money / Written the words to the prettiest tune / That would never leave a dry eye in the room," he proclaims. "My only excuse for not doing enough / Well I was too busy being in love."

  • "Why Didn't I Think of That"

    From: 'From the Heart' (1992)

    Although Stone continued to release well-received music through the mid-to-late 90s, this track from Bob McDill and Paul Harrison marks his most recent No. 1 hit to date. The playful "Why Didn't I Think of That" finds him looking back on a relationship he took for granted, coming to terms with his own shortcomings.

  • "I Never Knew Love"

    From: 'More Love' (1993)

    Stone gave fans a first taste of his fourth studio album More Love with this heartfelt lead single from brilliant songwriters Larry Boone and Will Robinson. Initially released in 1993, the track peaked at No. 2 on the country charts and became a surprise crossover success, even landing on Billboard's all-genre Hot 100 chart.

  • "Come In Out of the Pain"

    From: 'I Thought It Was You' (1991)

    Sent to radio in early 1992, this cut from I Thought It Was You is a lyrical plea for vulnerability from his partner. Instead of bottling up their emotions, Stone asks them to let the pain pour out to let the healing begin.

    "I'm happy that you're sad, I know that sounds so wrong / But darlin' you must know the pains gone on too long," he explains softly.

  • "Addicted to a Dollar"

    From: 'More Love' (1993)

    Stone teamed up with fellow songwriters Ray Hood, Kim Tribble and Ray Maddox to pen "Addicted to a Dollar," which gives a nod to hardworking blue-collar workers. The track, which peaked at No. 4 on country radio, vocalizes the everyday stresses of those just trying to make ends meet.

    "Got me more payments than I've got checks / Ten more to go on this car, it's a wreck," he explains with frustration. "Landlord's at my door, it's a life of hard knocks / When all I really want is my piece of the rock."

  • "Warning Labels"

    From: 'From the Heart' (1992)

    Stone's lead single from From the Heart is all about finding solace and healing through songs by country music icons like. In the track, he comes to the conclusion that those weepy, heartbreaking tunes can sometimes hit a little too hard.

    "They ought to put warning labels on those sad country songs," he declares. "Harmful to your heart when you're left all alone. "

  • "I Thought It Was You"

    From: 'I Thought It Was You' (1991)

    Written by Gary Harrison and Tim Mensy, "I Thought It Was You" served as the first single and title track off of Stone's second record, released in 1991. This engaging ballad finds the hitmaker lamenting over a lost love while finding himself searching for their face in passing crowds.

  • "These Lips Don't Know How to Say Goodbye"

    From: 'Doug Stone' (1990)

    Penned by legendary songwriter Harlan Howard, the declarative "These Lips Don't Know How to Say Goodbye" climbed into the Top 5 on the country airwaves following its release in 1990. In the song, Stone explains to his significant other how any attempt at ending their love affair would simply be in vain.

    "If you'd ask me, for the stars that shine above you / Then I could come much closer to the mark," he explains. "So don't stand there & tell me not to love you / Unless you stop the beating of my heart."

  • "I'd Be Better Off (In a Pine Box)"

    From: 'Doug Stone' (1990)

    Stone's impressive first single, "I'd Be Better Off (In a Pine Box)," was the perfect introduction into the genre. The magical combination of traditional country songwriting with his soulful vocal performance set the stage for a successful career, climbing to No. 4 on the country airplay chart and earning him a Grammy Award nomination for Best Male Country Vocal Performance.

  • "Fourteen Minutes Old"

    From: 'Doug Stone' (1990)

    The pain of a fresh heartbreak can make everything feel like it's happening in slow motion. In this Top 10 hit from 1990, Stone watches the clock as time slowly ticks by moments after his significant other says goodbye.

  • "Made for Lovin' You"

    From: 'From the Heart' (1992)

    Previously recorded by both Dan Seals and Clinton Gregory individually just a few years earlier, this co-write from acclaimed country songsmiths Sonny Throckmorton and Curly Putman also connected with Stone, who recorded it for his third record From the Heart. A celebration of a love that was built to last, "Made for Lovin' You" was another success for Stone, becoming a Top 10 hit on country radio.

  • "More Love"

    From: 'More Love' (1993)

    Many of Stone's most successful tracks are centered around the regret of letting a special relationship slip through the cracks. That type of mournful reflection is at the core of the Top 10 single "More Love," which Stone co-wrote along with Gary Burr.

    "I'd give her more love, more time / More of her knowing that she's on my mind," Stone admits in the sweeping chorus. "More of her heart would have suited her fine / Cause that's what she was dreaming of."

  • "Little Houses"

    From: 'Greatest Hits, Vol. 1' (1994)

    When Stone released Greatest Hits, Vol. 1 in 1994, just four years after his debut into the country music scene, he recorded "Little Houses" to serve as the only new track included in the collection. Written by Mickey Cates and Skip Ewing, the imagery-centered celebration of family and community became yet another Top 10 success for Stone.

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