Ricky Skaggs songs are some of the most beloved and most awarded in country music history.

The singer, producer and multi-instrumentalist has earned an astounding 14 Grammy Awards over the course of his career, which encompasses an early stint with bluegrass legend Ralph Stanley as well as appearances on a number of key albums from other artists before he struck out on his own as a commercial country solo artist with a decidedly traditional slant.

Skaggs' uncanny sense for picking songs with popular appeal, coupled with his vocal and instrumental prowess and that of his band, has landed him 12 No. 1 hits and a shelf full of Grammys, CMAs and IBMAs. He's scored success in several different genres, but The Boot's list of the Top 10 Ricky Skaggs Songs draws from his output as a commercial country artist.

  • 10

    "Uncle Pen"

    From: 'Don't Cheat in Our Hometown' (1983)

    Skaggs gives a nod to his traditional roots with this song, which Bill Monroe wrote as a tribute to his uncle and musical mentor, Pendleton Vandiver. The uptempo, fun tune is a perfect match for Skaggs' vocal and instrumental skills, and it gave him a No. 1 hit that was quite unlike the kind of music that was being recorded by any of his contemporaries.

  • 9

    "Cajun Moon"

    From: 'Live in London' (1985)

    Skaggs expanded his repertoire to include some Louisiana influences for this track, which was written by Jim Rushing. Released as the second single from Live in London, "Cajun Moon" was another excellent showcase for Skaggs and his top-notch band, and another No. 1 hit.

  • 8

    "Don't Cheat in Our Hometown"

    From: 'Don't Cheat in Our Hometown' (1983)

    Skaggs brought the tempo down for the title song of his sixth studio album. "Don't Cheat in Our Hometown" features a decidedly traditional slant, with steel, a classic groove and the high lonesome sound of Skaggs' lead vocal. The harmony stacks on the tag line alone make this one of the Top 10 Ricky Skaggs Songs.

  • 7

    "I Wouldn't Change You If I Could"

    From: 'Highways & Heartaches' (1982)

    "I Wouldn't Change You if I Could" is another track that allowed Skaggs to demonstrate that he could handle mid-tempo, vocal-oriented material as effectively as scorching instrumental fare. But the track is still perfectly framed in pedal steel and twin fiddles, adding just the right traditional touch for yet another No. 1 hit.

  • 6

    "Lovin' Only Me"

    From: 'Kentucky Thunder' (1989)

    Skaggs returned to No. 1 after an absence of several years with the first single from his 10th studio album. Written by Hillary Kanter and Even Stevens, "Lovin' Only Me" features a mid-tempo groove, big harmony vocals and twangy guitars that are in the classic style but just different enough from the rest of Skaggs' output to stand out. The song is his most recent No. 1 single to date.

  • 5

    "Love Can't Ever Get Better Than This"

    From: 'Love's Gonna Get Ya!' (1986)

    Skaggs and his wife, Sharon White of the Whites, scored a huge success with "Love Can't Ever Get Better Than This," their first-ever duet to be recorded and released as a single. The song not only scored them a Top 10 hit, it also earned them a CMA Award for Vocal Duo of the Year in 1987, though label politics prevented them from following up with an entire collaborative album until 2014's Hearts Like Ours.

  • 4


    From: 'Highways & Heartaches' (1982)

    Skaggs scored one of his most recognizable hits with this Guy Clark song. Previously recorded by Rodney Crowell, the tune was also cut by George Strait, but it was Skaggs' version that defined the song, reaching No. 1. In keeping with his policy of not recording any songs that he wouldn't feel comfortable singing in front of his parents, Skaggs changed one line to omit a curse word from his version.

  • 3

    "Honey (Open That Door)"

    From: 'Don't Cheat in Our Hometown' (1983)

    Skaggs scored one of his most spirited hits with "Honey (Open That Door)." The track contains some sweet instrumental fills and solos but really centers around Skaggs' vocal performance, as well as some enormous harmony vocal stacks that make the record sound panoramic. This tongue-in-cheek Mel Tillis song tells the story of a man who's asking his woman to let him back in after he's "lost everything but my name" in an ill-fated poker game.

  • 2

    "Highway 40 Blues"

    From: 'Highways & Heartaches' (1982)

    Skaggs is probably the only commercially successful country artist of his generation who could have even attempted "Highway 40 Blues" as a single and gotten away with it. The Larry Cordle song tells the story of a traveling musician who's wandered the highway for years and "squandered youth in search of truth," but it's the impressive instrumental solos that dominate the track and make it something truly special, with Skaggs' inimitable touch.

  • 1

    "Country Boy"

    From: 'Country Boy' (1984)

    Perhaps the defining song of Skaggs' career is "Country Boy," which brings together all of the elements that make his music special: The track features long instrumental interludes that may very well be the hottest bluegrass-style solos ever to appear on a commercial No. 1 hit, while none other than bluegrass pioneer Monroe appears in the entertaining video as Skaggs' Uncle Pen -- a humorous nod to a song of his that Skaggs also took to No. 1. "Country Boy" helped Skaggs earn the CMA Awards' Entertainer of the Year trophy and comes in at No. 1 on our list of the Top 10 Ricky Skaggs Songs.

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