The Fifty Best Debut Singles of All-Time: Part 3

The Fifty Best Debut Singles of All-Time

Part 3: #30-#21

#30     Toby Keith, “Should’ve Been a Cowboy”

Debut: March 6, 1993/Peak: #1

Take your pick: it’s the introduction of one of the best male vocalists of the past fifteen years, or the debut of one of its best songwriters. In the first verse of the song, he creates a fully believable back story to the Gunsmoke saga of Marshal Dillon and Miss Kitty, then pours his heart out with vocal conviction in the chorus, communicating the intensity of his wistful desire to have been a cowboy.

#29     LeAnn Rimes, “Blue”

Debut: May 25, 1996/Peak: #10

One of the few country records in modern times that launched a truly palpable buzz upon its launch, with Rimes being hailed as the second coming of Patsy Cline, despite being barely a teen as the single hit the airwaves. Eleven years later, the voice is still there, but she’s emerged as a surprisingly incisive songwriter as well.

#28     Faith Hill, “Wild One”

Debut: October 16, 1993/Peak: #1

What better way to launch the career of a fresh-faced young female vocalist than with a story song focused on a free-spirited teenage girl? It was a huge hit, but what’s most amazing listening to it today is to hear how her vocal style has changed. She started off with a mixture of Dolly’s sweetness and Reba’s twangy trills which sounds positively quaint next to her more recent recordings, but fits perfectly with the spirit of the song.

#27     Aaron Tippin, “You’ve Got to Stand For Something”

Debut: November 3, 1990/Peak: #6

We’re in an era where the voice of the working class has virtually disappeared from the country radio dial. Let’s be honest, country radio spends more time dealing with the highs and lows of teenage girls these days than it does on the working stiffs for whom high school is a distant memory. Aaron Tippin was country music’s last great working man’s hero, and his career started with an espousal of the values that he’d explore in most of his biggest hits.

#26     Loretta Lynn, “I’m a Honky Tonk Girl”

Debut: June 13, 1960/Peak: #14

Six years before she tore down the wall between what woman sing about and what they actually think and feel, Lynn traveled the country with her husband Mooney, personally promoting her debut single on Zero records. The trip is immortalized in Coal Miner’s Daughter – the book and the film – but on its own, it’s a fitting introduction to a fantastic singer-songwriter. She’s still singing like Kitty Wells, and the trademark sass is almost non-existent, but it’s a solid start nonetheless.

#25     Jan Howard, “The One You Slip Around With”

Debut: January 11, 1960/Peak: #13

Howard’s first major solo single finds her wishing she could be her husband’s mistress, because it would be a hell of a lot more fun than waiting for him to get home, after all his love and affection has been spent. That it got as high as #13 in 1960 is nothing short of astounding.

#24     Darryl Worley, “When You Need My Love”

Debut: April 1, 2000/Peak: #15

A record so good that it’s hard to believe a brand new artist was behind it. Worley’s tale of a man verbalizing his frustration at being the “rebound guy” for a woman he truly loves captures all of the conflicted emotions that go along with it, right down to his half-hearted insistence that someday, he won’t answer the call when she comes running into his arms.

#23     Lee Ann Womack, “Never Again, Again”

Debut: March 15, 1997/Peak: #23

Womack had them from the first twangy note of her debut single, and she was instantly heralded as country music’s traditional savior – the anti-Shania, if you will. Her talent has since proven to be quite versatile, but every time she returns to this style, like she did with the classic “I May Hate Myself in the Morning”, she’s at her musical best.

#22     The Judds, “Had a Dream (For the Heart)”

Debut: December 17, 1983/Peak: #17

I can only imagine what it was like to be around when this song first hit, hearing those perfect harmonies for the first time. When Wynonna went solo, some people sneered that Naomi wasn’t bringing much to the table in the first place, other than some pretty dresses. Some of their later singles did sound more like Wynonna was on her own, but when they first broke through, it was those perfect two-part harmonies that made them huge.

#21     Roger Miller, “You Don’t Want My Love”

Debut: October 31, 1960/Peak: #14

Also known as “In the Summertime,” Miller’s first chart hit is a head-spinning number, moving at a rapid-fire pace and connecting stream-of-consciousness vignettes with bursts of scatting in between. There’s been nothing like him in country music, before or since. When they call him a genuis, they’re not exaggerating.


  1. I was surprised to see “Blue” this early. I remember reading the charts in the Sunday Daily News and not knowing how to pronounce LeAnne because they wrote it LEANNE. It bothered me because the song was at #1 one for several weeks if I recall correctly and I hadn’t heard it or seen her.

    when you did the criteria did you count crossover success (eg a #15 country charting but a #1 pop) less than stricty country success?

  2. “Blue” didn’t reach #1 on any charts (#10 country, #26 Hot 100). Her only #1 songs have been “One Way Ticket” (country) and “How Do I Live” (adult contemporary).

  3. The album was #1 for like 28 weeks, but the song peaked at #10. It went up quickly and back down quickly, almost like a novelty hit would do.

    I didn’t think much about crossover success because it varies depending on the era. The period where the most artists had their first song be a hit (early-mid 90’s) was also the period where country artists got the least crossover exposure. It’s ultimately about the quality of the song, in addition to how well it established the artist and/or their sound. The songs that are higher on the list meet all three of those more consistently.

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