The 10 Best Ricky Skaggs Songs of All-Time

Ricky Skaggs

Rickie Lee Skaggs is an American neotraditional country and bluegrass singer, musician, producer, and composer born in Cordell, Kentucky, on July 18, 1954. He is a player of multiple instruments: mandolin, fiddle, guitar, mandocaster, and banjo, among others. At the age of 7, he first received a mandolin and started his musical career. He began playing bluegrass music with his brother and father, who had taught him how to play guitar during childhood. In 1976, he founded progressive bluegrass band Boone Creek and launched his solo career in 1980 after college graduation. Skaggs achieved 12 No. 1 hits, 8 CMA awards, and 8 ACM awards throughout his career. In 1982, he became a member of the Grand Ole Opry and is currently one of its most famous members there today. In 2016, he was inducted into the Musicians Hall of Fame and Museum. In 2018, he was inducted into the Country Music Hall of Fame. Thus, throughout his career, Skaggs has released 27 solo studio albums, with about 20 million copies sold worldwide. So far, he has received 29 Grammy Awards nominations winning 14 of them.

10. Honey (Open That Door) (1985)


“Honey Open That Door” was released in March 1985 under Highways & Heartaches. The best way to describe this song is that it’s a simple but fun and infectious tune that you could play over and over again without ever getting tired of it. He sings about good times with his good friend, who happens to be a beautiful woman to whom he has a strong attraction and wants nothing more than to get closer. In other words, he sings about having a crush on her and wanting to build a strong friendship with her while working his way up from being just friends to being more than that.

9. Don’t Cheat in Our Hometown (1993)


“Don’t Cheat in Our Hometown” was released under Skaggs’s album Super Hits. The song talks about Skaggs’ hometown where everything happens, like telling off someone who cheats in it or talking about all the great people who live there. The song sounds nostalgic with its storytelling about a place that’s always been good to its residents despite their faults, but it still has room for improvement.

8. You’ve Got A Lover (1982)


“You’ve Got A Lover,” released 1982 under Highways & Heartaches album, talks about how there is always someone special in one’s life who keeps one warm and happy no matter what happens in life. Someone worth having in your life when times get hard and give you peace of mind when everything else fails. So he would do anything to keep that person with him forever so they’ll never part ways because he knows she means too much for him to ever lose her like that as he did once before, which convinced him not to let go of her again but fight to keep her by his side this time around.

7. Highway 40 Blues (1985)


“Highway 40 Blues” was released in 1985 under Skaggs’s album Highways & Heartaches. The song talks about how he loves to drive on that highway. Still, sometimes other drivers are inconsiderate of other drivers, creating a dangerous situation and making him fear his life. As a result, he would like them to know how it feels whenever they make someone feel like they might not make it because of their selfishness.

6. I Wouldn’t Change You If I Could (1982)


“I Wouldn’t Change You If I Could” from Highways & Heartaches album released in 1982 under the same title. The song talks about him falling hard for a woman he’s known for a while and wishes that she would see how much of a good person he is, or else it will all be a waste because nothing will ever happen between them if she doesn’t realize what her true feelings are for him. He compares himself to a bed of roses wanting to be given away by her, but at the same time, he knows no matter what anyone says about him, he’ll still love her until the day comes when they can be together forever.

5. Heartbroke (1982)


“Heartbroken” was released under Highways & Heartaches album in 1982 with the same title. The song talks about how he has been heartbroken from losing someone who meant a lot to him, which made him realize how fragile love can be and that one should never take it for granted. How sometimes what you thought was true love ends up being a lie, leaving you heartbroken and alone after realizing you wasted all those years of your life on something that wasn’t even worth it at the end of the day. Skaggs sings this song with conviction making listeners feel his pain while empathizing with his situation because we’ve all been there at least once.

4. I Don’t Care (1981)


“I Don’t Care” from Skaggs’s album Waitin’ for the Sun to Shine was released in 1981 under the same title with a bluegrass music sound which talks about a man who is very much in love with a woman and doesn’t care if she has faults as long as he gets to spend his life with her forever. He’s willing to put up with whatever it takes to make that happen even if they argue over something as little as what time the sun rises, as long as they can be together doing it all over again another day because loving her fills him up inside making him whole again after losing someone else he loved before.

3. Crying My Heart Out Over You (1981)


“Crying My Heart Out Over You” was released in 1981 under Skaggs’s album Waitin’ for the Sun to Shine with the same title. The song talks about how even though he is falling in love, his heart seems to be mourning someone he loved before. He imagines if it had been another day where they would have met again at some point, but of course, it wasn’t giving him any choice but to let go of all those memories and move on with his life eventually. However, there are times when he can’t help himself yet can’t do anything about it because of afraid of being rejected by her again, which would only make him feel worse.

2. You May See Me Walkin’ (1981)


“You May See Me Walkin'” was released in 1981 under Skaggs’s album Waitin’ for the Sun to Shine with the same title. The song talks about how he loves a woman, but she doesn’t know it yet. He watches her whenever they are together, noticing how happy she seems when being surrounded by all those people, wishing that one day maybe she’ll notice him the way he does to her. There are times where he can see himself walking away if things didn’t work out between them wondering if there would be anything that could bring him back to her or if he should just leave because it might be better off that way knowing how hard loving her can be.

1. Don’t Get Above Your Raising (1981)


“Don’t Get Above Your Raising” from Skaggs’s album Waitin’ for the Sun to Shine, released in 1981 under the same title, talks about a man who doesn’t care what kind of life he leads or how much money he has because all that matters is getting to spend forever with his loved one doing whatever it takes to make sure their relationship lasts and is strong even when times get tough. Despite everything, they manage to pull through them together with no matter what happens. The song brings out feelings we all have at least once in our lives when it comes to love, making listeners feel just as happy and content as if they were the ones being sung to.


Ricky Skaggs is an outstanding country music singer-songwriter who has helped shape today’s music by introducing bluegrass sounds into mainstream country songs. His talent and genius influenced countless artists such as Keith Urban, Patty Loveless, and even Brad Paisley. He has earned many prestigious awards over his 42 -year career in the industry, including Grammy Awards, Country Music Association Awards, Dove Awards, among others which attest to how well respected he is in the business making him one of the best vocalists of all time.

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