Complete List Of Ricky Skaggs Songs From A to Z

Feature Photo: Steve Proctor, CC BY-SA 4.0, via Wikimedia Commons

Ricky Skaggs brought bluegrass musicianship into the mainstream of country music without losing the musical traditions that first inspired him. Born in Cordell, Kentucky, on July 18, 1954, he began playing mandolin as a young child and was performing with established musicians before reaching his teens. His unusually broad career has taken him from mountain bluegrass to platinum-selling country albums, gospel recordings, instrumentals, and collaborations with artists from several musical generations.

A defining early partnership developed with fellow Kentucky musician Keith Whitley. After performing for Ralph Stanley, the two teenagers joined his Clinch Mountain Boys and made recordings together, including a tribute to the Stanley Brothers and Second Generation Bluegrass. Skaggs subsequently worked with J.D. Crowe and the New South, helped lead Boone Creek, and became part of Emmylou Harris’s Hot Band. Those experiences shaped his mandolin, fiddle, and harmony singing long before his commercial country breakthrough.

His first major run of country success began with Waitin’ for the Sun to Shine in 1981. Recordings such as ‘Crying My Heart Out Over You,’ ‘Heartbroke,’ ‘Highway 40 Blues,’ ‘Don’t Cheat in Our Hometown,’ ‘Honey (Open That Door),’ ‘Uncle Pen,’ and ‘Country Boy’ made Skaggs one of country music’s defining voices of the 1980s. His arrangements used acoustic instruments and traditional material at a moment when much of Nashville favored a smoother production style.

Skaggs continued recording country music into the 1990s before returning decisively to bluegrass with Kentucky Thunder. Albums such as Bluegrass Rules!, Ancient Tones, Soldier of the Cross, and Brand New Strings showed a commanding bandleader who placed spirited instrumental playing alongside traditional gospel, mountain ballads, and original material. He also recorded with Tony Rice, Bruce Hornsby, the Whites, and his wife Sharon White, and assembled tributes to Bill Monroe and bluegrass’s early recording pioneers.

His catalog did not end with the acclaimed 2014 duet album Hearts Like Ours. Skaggs continued releasing collaborations and standalone recordings, including new music in 2025 and the 2026 single ‘Say a Prayer.’ Across this extensive body of work, his recordings reflect a musician who has continually connected country, bluegrass, faith, and the artistry of traditional American string music.

Complete List Of Ricky Skaggs Songs From A to Z

0–E

“21 Fiddle Salute” – That’s It! (1975)
“A Brand New Me” – Country Boy (1984)
“Across the Rocky Mountain” – Ricky Skaggs & Bruce Hornsby (2007), with Bruce Hornsby
“A Few More Seasons to Come” – Gospel Echoes and White Doves (1983)
“A Hard Row to Hoe” – Love’s Gonna Get Ya! (1986)
“Ain’t Love a Good Thing” – Life Is a Journey (1997)
“Ain’t Nobody Gonna Miss Me” – Boone Creek (1977), with Boone Creek
“All I Ever Loved Was You” – Second Generation Bluegrass (1972), with Keith Whitley
“Amanda Jewell” – Bluegrass Rules! (1997)
“A Night on the Town” – Ricky Skaggs & Bruce Hornsby (2007), with Bruce Hornsby
“Another Night” – Bluegrass Rules! (1997)
“Another Song, Another Drink” – Gospel Echoes and White Doves (1983)
“Appalachian Joy” – Brand New Strings (2004)
“Are You Afraid to Die” – Soldier of the Cross (1999)
“Are You Proud of America?” – Gospel Echoes and White Doves (1983)
“Artificial Heart” – Love’s Gonna Get Ya! (1986)
“A Vision of Mother” – Don’t Cheat in Our Hometown (1983)
“A Voice from on High” – Soldier of the Cross (1999)
“Away in a Manger” – A Skaggs Family Christmas Live (bonus DVD) (2011)
“A Work of Love” – Mosaic (2010)
“A Wound Time Can’t Erase” – Don’t Cheat in Our Hometown (1983)
“Baby Girl” – Sweet Temptation (1979)
“Baby I’m in Love with You” – Sweet Temptation (1979)
“Back Where We Belong” – Solid Ground (1995)
“Banks of the Ohio” – New South Live (1975)
“Battle Cry (Ram’s Horn)” – Soldier of the Cross (1999)
“Be Kind” – Hearts Like Ours (2014), with Sharon White
“Big Mon” – Big Mon: The Songs of Bill Monroe (2000), with various featured artists
“Big Wheel” – Salt of the Earth (2007), with the Whites
“Black Eyed Susie” – Live at the Charleston Music Hall (2003)
“Blessed Assurance” – Salt of the Earth (2007), with the Whites
“Blue and Lonesome Too” – One Way Track (1978), with Boone Creek
“Bluegrass Breakdown” – Honoring the Fathers of Bluegrass: Tribute to 1946 and 1947 (2008)
“Blue Moon of Kentucky” – Big Mon: The Songs of Bill Monroe (2000), with John Fogerty
“Blue Night” – Big Mon: The Songs of Bill Monroe (2000), with Mary Chapin Carpenter
“Blue Night (Simply Bluegrass)” – Blue Night (Simply Bluegrass) single (2021)
“Boone Creek” – Boone Creek (1977), with Boone Creek
“Boston Boy” – Ancient Tones (1999)
“Bowtie” – Bowtie single (2026), with Mark O’Connor, Vince Gill and Steve Wariner
“Branded Wherever I Go” – Solo: Songs My Dad Loved (2009)
“Brand New Strings” – Brand New Strings (2004)
“Brightest and Best” – Brightest and Best single (2021), with Keith & Kristyn Getty
“Buckwheat” – Gospel Echoes and White Doves (1983)
“Bugle Call Rag” – New South Live (1975)
“Bury Me Beneath the Weeping Willow” – Skaggs & Rice (1980), with Tony Rice
“Cajun Moon” – Live in London (1985)
“Cajun Moon (Bluegrass version)” – Country Hits Bluegrass Style (2011)
“Callin’ Your Name” – Solid Ground (1995)
“Calloway” – Solo: Songs My Dad Loved (2009)
“Can’t Control the Wind” – Solid Ground (1995)
“Can’t Shake Jesus” – Mosaic (2010)
“Can’t You Hear Me Callin'” – Highways & Heartaches (1982)
“Can’t You Hear Me Calling” – One Way Track (1978), with Boone Creek
“Carolina Mountain Home” – Ancient Tones (1999)
“Casting My Shadow in the Road” – Kentucky Thunder (1989)
“Cat’s in the Cradle” – Solid Ground (1995)
“Children Go” – A Skaggs Family Christmas: Volume Two (2011), with the Whites and family
“Children Go Where I Send Thee” – Don’t Cheat in Our Hometown (1983)
“Christmas Time Is Here” – A Skaggs Family Christmas: Volume One (2005), with the Whites and family
“Christmas Time’s a-Coming” – A Skaggs Family Christmas: Volume Two (2011), with the Whites and family
“City That Lies Foursquare” – Solo: Songs My Dad Loved (2009)
“Close By” – Big Mon: The Songs of Bill Monroe (2000), with Patty Loveless
“Cluck Ol’ Hen” – Cluck Ol’ Hen (2013)
“Coal Minin’ Man” – Ancient Tones (1999)
“Colonel Prentiss” – Solo: Songs My Dad Loved (2009)
“Come on Out” – Ricky Skaggs & Bruce Hornsby (2007), with Bruce Hornsby
“Connemara” – Ancient Tones (1999)
“Could You Love Me One More Time” – Sweet Temptation (1979)
“Country Boy” – Country Boy (1984)
“Country Boy (Bluegrass version)” – Country Hits Bluegrass Style (2011)
“Crossing the Briney” – Instrumentals (2006)
“Crossville” – Live at the Charleston Music Hall (2003)
“Crown of Jewels” – Ricky Skaggs & Bruce Hornsby (2007), with Bruce Hornsby
“Cry, Cry Darlin'” – Big Mon: The Songs of Bill Monroe (2000), with Dolly Parton
“Cry, Cry Darling” – Solid Ground (1995)
“Crying My Heart Out Over You” – Waitin’ for the Sun to Shine (1981)
“Crying My Heart Out Over You (Bluegrass version)” – Country Hits Bluegrass Style (2011)
“Cryin’ Holy” – J.D. Crowe & the New South (1975), with J.D. Crowe and the New South
“Daddy Was a Hard Working Honest Man” – Love’s Gonna Get Ya! (1986)
“Daniel Prayed” – One Way Track (1978), with Boone Creek
“Dark Hollow” – New South Live (1975)
“Dark Is the Night” – Boone Creek (1977), with Boone Creek
“Darktown Strutters Ball” – That’s It! (1975)
“Darlin’ Corey” – Big Mon: The Songs of Bill Monroe (2000), with Bruce Hornsby
“Darling Corey” – Cluck Ol’ Hen (2013)
“Dawg’s Breath” – Instrumentals (2006)
“Daybreak Blues” – The Three Pickers (2003)
“Daybreak in Dixie” – Second Generation Bluegrass (1972), with Keith Whitley
“Deck the Halls” – A Skaggs Family Christmas: Volume One (2005), with the Whites and family
“Dim Lights, Thick Smoke (And Loud, Loud Music)” – History of the Future (2001)
“Dixieland” – Boone Creek (1977), with Boone Creek
“Doin’ My Time” – The Three Pickers (2003)
“Don’t Cheat in Our Hometown” – Second Generation Bluegrass (1972), with Keith Whitley
“Don’t Cheat in Our Hometown (1983 country recording)” – Don’t Cheat in Our Hometown (1983)
“Don’t Get Above Your Raising” – Waitin’ for the Sun to Shine (1981)
“Don’t Get Above Your Raising (Bluegrass version)” – Country Hits Bluegrass Style (2011)
“Don’t Let Your Deal Go Down” – The Three Pickers (2003)
“Don’t Let Your Sweet Love Die” – Highways & Heartaches (1982)
“Don’t Step Over an Old Love” – Don’t Cheat in Our Hometown (1983)
“Don’t Stop Gypsy” – Love’s Gonna Get Ya! (1986)
“Don’t Think I’ll Cry” – Highways & Heartaches (1982)
“Don’t You Believe” – That Down Home Feeling (1977), with Buck White and the Down Home Folks
“Down Home Waltz” – That Down Home Feeling (1977), with Buck White and the Down Home Folks
“Down in the Valley to Pray” – The Three Pickers (2003)
“Do You Hear What I Hear?” – A Skaggs Family Christmas: Volume One (2005), with the Whites and family
“Dream of a Miner’s Child” – Second Generation Bluegrass (1972), with Keith Whitley
“Drifting Too Far from the Shore” – Boone Creek (1977), with Boone Creek
“Drunken Driver” – Bluegrass Rules! (1997)
“Earl’s Breakdown” – The Three Pickers (2003)
“East Virginia Blues” – New South Live (1975)
“Enjoy the Ride” – Brand New Strings (2004)
“Every Drop of Water” – Solid Ground (1995)

F–J

“Fancy Dan” – That Down Home Feeling (1977), with Buck White and the Down Home Folks
“Farther Along” – Salt of the Earth (2007), with the Whites
“Father Knows Best” – My Father’s Son (1991)
“Feast Here Tonight” – The Three Pickers (2003)
“Fire from the Sky” – Mosaic (2010)
“Flight to Egypt” – A Skaggs Family Christmas: Volume Two (2011), with the Whites and family
“Florida Blues” – That’s It! (1975)
“Foggy Mountain Top” – The Three Pickers (2003)
“Foggy River” – Solo: Songs My Dad Loved (2009)
“Forever’s Not Long Enough” – Hearts Like Ours (2014), with Sharon White
“Forgive Me” – Sweet Temptation (1979)
“From the Word Love” – My Father’s Son (1991)
“Gallatin Rag” – Instrumentals (2006)
“Gathering Flowers for the Master’s Bouquet” – Gospel Echoes and White Doves (1983)
“General Greene” – General Greene single (2025)
“Get Up John” – Bluegrass Rules! (1997)
“Give Us a Happy Home” – My Father’s Son (1991)
“Give Us Rain” – Ancient Tones (1999)
“God Holds the Future in His Hands” – Solo: Songs My Dad Loved (2009)
“God’s Own Singer” – New South Live (1975)
“Going Back to Old Kentucky” – Honoring the Fathers of Bluegrass: Tribute to 1946 and 1947 (2008)
“Going to Richmond” – Instrumentals (2006)
“Goin’ to the Ceili” – Live at the Charleston Music Hall (2003)
“Gone Home” – Soldier of the Cross (1999)
“Gonna Settle Down” – Boone Creek (1977), with Boone Creek
“Go Tell It on the Mountain” – A Skaggs Family Christmas Live (bonus DVD) (2011)
“Go Thee Down” – A Skaggs Family Christmas: Volume One (2005), with the Whites and family
“Green Pastures in the Sky” – Solo: Songs My Dad Loved (2009)
“Gulf of Mexico Fishing Boat Blues” – Ricky Skaggs & Bruce Hornsby (2007), with Bruce Hornsby
“Halfway Home Cafe” – History of the Future (2001)
“Hallelujah I’m Ready” – Family & Friends (1982)
“Hangin’ Around the Mistletoe” – A Skaggs Family Christmas: Volume One (2005), with the Whites and family
“Have Yourself a Merry Little Christmas” – A Skaggs Family Christmas: Volume One (2005), with the Whites and family
“Have You Someone (In Heaven a Waiting)” – Skaggs & Rice (1980), with Tony Rice
“Head Over Heels” – One Way Track (1978), with Boone Creek
“Head Over Heels in Love with You” – Don’t Cheat in Our Hometown (1983)
“Heartbreak Hurricane” – Kentucky Thunder (1989)
“Heartbroke” – Highways & Heartaches (1982)
“Heartbroke (Bluegrass version)” – Country Hits Bluegrass Style (2011)
“Hearts Like Ours” – Hearts Like Ours (2014), with Sharon White
“Hearts Like Ours (Sweethearts)” – Hearts Like Ours (Sweethearts) single (2022), with Sharon White
“Heavy Traffic Ahead” – Big Mon: The Songs of Bill Monroe (2000), with Steve Wariner
“He Was On to Somethin’ (So He Made You)” – Kentucky Thunder (1989)
“He Was On to Somethin’ (So He Made You) (Bluegrass version)” – Country Hits Bluegrass Style (2011)
“Highway 40 Blues” – Highways & Heartaches (1982)
“Highway 40 Blues (Bluegrass version)” – Country Hits Bluegrass Style (2011)
“Hillbilly Highway” – Life Is a Journey (1997)
“Hills of Mexico” – Ricky Skaggs & Bruce Hornsby (2007), with Bruce Hornsby
“Hold On Tight (Let It Go)” – My Father’s Son (1991)
“Hold On Tight (Let It Go) (2014 duet with Sharon White)” – Hearts Like Ours (2014)
“Hold Whatcha Got” – Comin’ Home to Stay (1988)
“Home Is Wherever You Are” – Comin’ Home to Stay (1988)
“Home Is Wherever You Are (2014 duet with Sharon White)” – Hearts Like Ours (2014)
“Homesick for Heaven” – Salt of the Earth (2007), with the Whites
“Home Sweet Home Revisited” – J.D. Crowe & the New South (1975), with J.D. Crowe and the New South
“Honey (Open That Door)” – Don’t Cheat in Our Hometown (1983)
“Honey (Open That Door) (Bluegrass version)” – Country Hits Bluegrass Style (2011)
“Hook and Line” – That’s It! (1975)
“How Mountain Girls Can Love” – Ancient Tones (1999)
“Hulla Gull” – Gospel Echoes and White Doves (1983)
“Hummingbird” – Kentucky Thunder (1989)
“I Ain’t Never” – Solid Ground (1995)
“I Am a Pilgrim” – Big Mon: The Songs of Bill Monroe (2000), with Charlie Daniels
“I Am Bluegrass” – I Am Bluegrass single (2026), with bluegrass all-star ensemble
“I Believed in You Darling” – Ancient Tones (1999)
“I Believe in Music” – That Down Home Feeling (1977), with Buck White and the Down Home Folks
“I Corinthians 1:18” – Brand New Strings (2004)
“I Don’t Care” – Waitin’ for the Sun to Shine (1981)
“I Don’t Care (Bluegrass version)” – Country Hits Bluegrass Style (2011)
“I Don’t Remember Forgetting” – Life Is a Journey (1997)
“If I Had It All Again to Do” – Brand New Strings (2004)
“If I Lose” – Bluegrass Rules! (1997)
“If I Needed You” – Hearts Like Ours (2014), with Sharon White
“If That’s the Way You Feel” – Waitin’ for the Sun to Shine (1981)
“If You Don’t Believe the Bible” – Comin’ Home to Stay (1988)
“I Had but Fifty Cents” – Solo: Songs My Dad Loved (2009)
“I Heard My Mother Call My Name in Prayer” – Live at the Charleston Music Hall (2003)
“I Hope You’ve Learned” – Bluegrass Rules! (1997)
“I Know What It Means to Be Lonesome” – Sweet Temptation (1979)
“I’ll Stay Around” – Sweet Temptation (1979)
“I’ll Take the Blame” – Sweet Temptation (1979)
“I Long to See the Old Folks” – Tribute to the Stanley Brothers (1971), with Keith Whitley
“I Love No One but You” – Tribute to the Stanley Brothers (1971), with Keith Whitley
“I’m Awake Now” – Mosaic (2010)
“I’m Beside Myself” – Love’s Gonna Get Ya! (1986)
“I’m Lost and I’ll Never Find the Way” – Family & Friends (1982)
“I’m Ready to Go” – Country Boy (1984)
“I’m Tired” – Comin’ Home to Stay (1988)
“I’m Walkin'” – J.D. Crowe & the New South (1975), with J.D. Crowe and the New South
“In Heaven We’ll Never Grow Old” – Gospel Echoes and White Doves (1983)
“Instead” – Mosaic (2010)
“In the Pines” – One Way Track (1978), with Boone Creek
“Intro” – Boone Creek (1977), with Boone Creek
“I Run to You” – Hearts Like Ours (2014), with Sharon White
“It’s Mighty Dark to Travel” – Ancient Tones (1999)
“It’s Never Too Late (To Start Over New)” – Tribute to the Stanley Brothers (1971), with Keith Whitley
“It Sure Rains Hard in Tennessee” – That Down Home Feeling (1977), with Buck White and the Down Home Folks
“It Takes Three” – Hearts Like Ours (2014), with Sharon White
“I’ve Got a New Heartache” – Live in London (1985)
“I Was Meant to Love You” – Hearts Like Ours (2014), with Sharon White
“I Wonder If I Care as Much” – Love’s Gonna Get Ya! (1986)
“I Won’t Let You Down” – Love’s Gonna Get Ya! (1986)
“I Wouldn’t Change You If I Could” – Highways & Heartaches (1982)
“I Wouldn’t Change You If I Could (Bluegrass version)” – Country Hits Bluegrass Style (2011)
“Jacob’s Vision” – Soldier of the Cross (1999)
“J.D.’s Words of Wisdom” – Bluegrass Rules! (1997)
“Jesus Hold My Hand” – Jesus Hold My Hand single (2023), with Jeff & Sheri Easter
“Jingle Bells” – Jingle Bells single (2019), with Dionne Warwick, John Rich and the Oak Ridge Boys
“Jordan” – Jordan single (2023), with Mo Pitney and Mark Fain
“Joy to the World” – A Skaggs Family Christmas: Volume Two (2011), with the Whites and family
“Just the Two of Us” – Solid Ground (1995)

K–O

“Katy Hill” – The Three Pickers (2003)
“Keep a Memory” – Don’t Cheat in Our Hometown (1983)
“Keep My Love with You” – Gospel Echoes and White Doves (1983)
“Kentucky Thunder” – Kentucky Thunder (1989)
“Lead Me to the Rock” – Soldier of the Cross (1999)
“Leaning on Jesus” – Gospel Echoes and White Doves (1983)
“Let It Be You” – Kentucky Thunder (1989)
“Let It Shine” – Salt of the Earth (2007), with the Whites
“Let It Snow, Let It Snow” – A Skaggs Family Christmas: Volume One (2005), with the Whites and family
“Let Me Walk Lord, by Your Side” – Gospel Echoes and White Doves (1983)
“Let’s Keep Old Glory Waving” – Gospel Echoes and White Doves (1983)
“Let’s Love the Bad Times Away” – Highways & Heartaches (1982)
“Let’s Put Love Back to Work” – Life Is a Journey (1997)
“Life’s Too Long (To Live Like This)” – My Father’s Son (1991)
“Light of the Stable” – A Skaggs Family Christmas: Volume Two (2011), with the Whites and family
“Little Bessie” – Ancient Tones (1999)
“Little Cabin Home on the Hill” – Sweet Temptation (1979)
“Little Community Church” – One Way Track (1978), with Boone Creek
“Little Drummer Boy” – A Skaggs Family Christmas: Volume One (2005), with the Whites and family
“Little Glass of Wine” – Tribute to the Stanley Brothers (1971), with Keith Whitley
“Little Maggie” – Bluegrass Rules! (1997)
“Lonesome and Dry as a Bone” – Brand New Strings (2004)
“Lonesome Dove” – Life Is a Journey (1997)
“Lonesome for You” – Kentucky Thunder (1989)
“Lonesome Night” – Ancient Tones (1999)
“Lonesome River” – Tribute to the Stanley Brothers (1971), with Keith Whitley
“Lonesome Wind Blues” – That Down Home Feeling (1977), with Buck White and the Down Home Folks
“Lord She Sure Is Good at Lovin’ Me” – Comin’ Home to Stay (1988)
“Lost to a Stranger” – Waitin’ for the Sun to Shine (1981)
“Love Came Gently” – A Skaggs Family Christmas: Volume One (2005), with the Whites and family
“Love Can’t Ever Get Better Than This” – Love’s Gonna Get Ya! (1986)
“Love Can’t Ever Get Better Than This (2014 duet with Sharon White)” – Hearts Like Ours (2014)
“Love Does It Every Time” – Brand New Strings (2004)
“Love’s Gonna Get You Someday” – Love’s Gonna Get Ya! (1986)
“Love Will Be Enough” – Salt of the Earth (2007), with the Whites
“Loving You Too Well” – Tribute to the Stanley Brothers (1971), with Keith Whitley
“Lovin’ Only Me” – Kentucky Thunder (1989)
“Lovin’ Only Me (Bluegrass version)” – Country Hits Bluegrass Style (2011)
“Low and Lonely” – Waitin’ for the Sun to Shine (1981)
“Make God First” – Mosaic (2010)
“Mandolin Rain” – Ricky Skaggs & Bruce Hornsby (2007), with Bruce Hornsby
“Mansions for Me” – Skaggs & Rice (1980), with Tony Rice
“Mary, Did You Know?” – A Skaggs Family Christmas: Volume One (2005), with the Whites and family
“Meetin’ House Branch” – That’s It! (1975)
“Memories of Mother” – Second Generation Bluegrass (1972), with Keith Whitley
“Memories of Mother and Dad” – Skaggs & Rice (1980), with Tony Rice
“Missing Vassar” – Instrumentals (2006)
“Mississippi Queen” – One Way Track (1978), with Boone Creek
“Monroe Dancin'” – Brand New Strings (2004)
“Montana Slim” – Instrumentals (2006)
“Mosaic” – Mosaic (2010)
“Mother No Longer Awaits Me at Home” – Tribute to the Stanley Brothers (1971), with Keith Whitley
“Mother’s Only Sleeping” – History of the Future (2001)
“Music to My Ears” – Music to My Ears (2012)
“My Cup Runneth Over” – Mosaic (2010)
“My Deceitful Heart” – Second Generation Bluegrass (1972), with Keith Whitley
“My Father’s Son” – My Father’s Son (1991)
“My Little Georgia Rose” – Big Mon: The Songs of Bill Monroe (2000), with Travis Tritt
“Nashville Blues” – J.D. Crowe & the New South (1975), with J.D. Crowe and the New South
“Near the Cross” – Salt of the Earth (2007), with the Whites
“New Jerusalem” – Music to My Ears (2012)
“New Star Shining” – Love’s Gonna Get Ya! (1986)
“No Doubt About It” – Hearts Like Ours (2014), with Sharon White
“No Mother or Dad” – One Way Track (1978), with Boone Creek
“Nothing Beats a Family” – Music to My Ears (2012)
“Nothing Can Hurt You” – Highways & Heartaches (1982)
“O Come, O Come, Emmanuel” – A Skaggs Family Christmas: Volume Two (2011), with the Whites and family
“Old Enough” – Consolation (2008), with The Raconteurs and Ashley Monroe
“Old Home” – History of the Future (2001)
“Old Home Place” – J.D. Crowe & the New South (1975), with J.D. Crowe and the New South
“Old Kind of Love” – Comin’ Home to Stay (1988)
“On a Lonesome Night” – Live at the Charleston Music Hall (2003)
“One Seed of Love” – Salt of the Earth (2007), with the Whites
“One Way Rider” – Highways & Heartaches (1982)
“One Way Track” – One Way Track (1978), with Boone Creek
“Only Daddy That’ll Walk the Line” – My Father’s Son (1991)
“On the Old Kentucky Shore” – Big Mon: The Songs of Bill Monroe (2000), with Joan Osborne
“Our Last Goodbye” – Tribute to the Stanley Brothers (1971), with Keith Whitley

P–T

“Patiently Waiting” – Country Boy (1984)
“Pick Along” – The Three Pickers (2003)
“Pickin’ in Caroline” – Solo: Songs My Dad Loved (2009)
“Picture” – Mosaic (2010)
“Pig in a Pen” – Ancient Tones (1999)
“Polk City” – Instrumentals (2006)
“Poor Monroe” – Second Generation Bluegrass (1972), with Keith Whitley
“Put It Off Until Tomorrow” – Sweet Temptation (1979)
“Rain” – That Down Home Feeling (1977), with Buck White and the Down Home Folks
“Raisin’ the Dickens” – Love’s Gonna Get Ya! (1986)
“Rank Stranger” – Bluegrass Rules! (1997)
“Rawhide” – Bluegrass Rules! (1997)
“Reasons to Hang On” – Hearts Like Ours (2014), with Sharon White
“Red Apple Rag” – That’s It! (1975)
“Remember the Cross” – Soldier of the Cross (1999)
“Rendezvous” – Country Boy (1984)
“Restless” – The New Nashville Cats (1991), with Mark O’Connor, Vince Gill and Steve Wariner
“Restless (2026 recording)” – Restless single (2026)
“Return to Sender” – Mosaic (2010)
“Reunion Song” – A Skaggs Family Christmas: Volume Two (2011), with the Whites and family
“Ridin’ That Midnight Train” – Bluegrass Rules! (1997)
“River of Memory” – Family & Friends (1982)
“River Underground” – Gospel Echoes and White Doves (1983)
“Road to Spencer” – History of the Future (2001)
“Rock Bottom” – Gospel Echoes and White Doves (1983)
“Rockin’ the Boat (Live)” – Live in London (1985)
“Rock Salt & Nails” – J.D. Crowe & the New South (1975), with J.D. Crowe and the New South
“Rocky Road Blues” – Big Mon: The Songs of Bill Monroe (2000), with Dwight Yoakam
“Rollin’ in My Sweet Baby’s Arms” – History of the Future (2001)
“Roll in My Sweet Baby’s Arms” – New South Live (1975)
“Sally Gooden” – One Way Track (1978), with Boone Creek
“Sally Goodin” – J.D. Crowe & the New South (1975), with J.D. Crowe and the New South
“Sally Jo” – Brand New Strings (2004)
“Salt of the Earth” – Salt of the Earth (2007), with the Whites
“Same Old Train” – Tribute to Tradition (1998), with various artists
“Same Ol’ Love” – My Father’s Son (1991)
“San Antonio Rose” – Comin’ Home to Stay (1988)
“Santa Claus Is Coming to Town” – A Skaggs Family Christmas Live (bonus DVD) (2011)
“Satisfy My Mind” – Boone Creek (1977), with Boone Creek
“Saviour, Save Me from Myself” – Kentucky Thunder (1989)
“Sawin’ on the Strings” – History of the Future (2001)
“Say a Prayer” – Say a Prayer single (2026)
“Say Won’t You Be Mine” – Family & Friends (1982)
“Sea of Regret” – Second Generation Bluegrass (1972), with Keith Whitley
“Seven Bridges Road (Live at the Grand Ole Opry)” – Seven Bridges Road (Live at the Grand Ole Opry) single (2019)
“Seven Hillsides” – Soldier of the Cross (1999)
“Shady Grove” – History of the Future (2001)
“She Didn’t Say Why (Live)” – Live in London (1985)
“Sheep Shell Corn” – Ricky Skaggs & Bruce Hornsby (2007), with Bruce Hornsby
“Shepherd’s Voice” – Mosaic (2010)
“She’s More to Be Pitied” – Don’t Cheat in Our Hometown (1983)
“Shouting on the Hills of Glory” – Gospel Echoes and White Doves (1983)
“Silent Night” – A Skaggs Family Christmas: Volume Two (2011), with the Whites and family
“Simple Life” – My Father’s Son (1991)
“Sin City” – New South Live (1975)
“Sinner You’d Better Get Ready” – Solo: Songs My Dad Loved (2009)
“Sis Draper” – Brand New Strings (2004)
“Soldier of the Cross” – Soldier of the Cross (1999)
“Soldier’s Joy” – The Three Pickers (2003)
“Soldier’s Son” – Music to My Ears (2012)
“Solid Ground” – Solid Ground (1995)
“Somebody’s Prayin'” – My Father’s Son (1991)
“Somebody’s Prayin’ (Bluegrass version)” – Country Hits Bluegrass Style (2011)
“Someday Soon” – Mosaic (2010)
“Somehow Tonight” – Bluegrass Rules! (1997)
“Some Old Day” – J.D. Crowe & the New South (1975), with J.D. Crowe and the New South
“Something in My Heart” – Country Boy (1984)
“Somewhere Nice Forever” – Live at the Charleston Music Hall (2003)
“Son of Hobert” – Second Generation Bluegrass (1972), with Keith Whitley
“So Round, So Firm, So Fully Packed” – Waitin’ for the Sun to Shine (1981)
“Southern Moon” – That’s It! (1975)
“Southern Select” – That Down Home Feeling (1977), with Buck White and the Down Home Folks
“Spam Jelly” – Instrumentals (2006)
“Spontaneous Worship” – Mosaic (2010)
“Spread a Little Love Around” – Brand New Strings (2004)
“Step of Faith” – Step of Faith (1996), with Carman
“Stoney Creek” – New South Live (1975)
“Straight to You” – Life Is a Journey (1997)
“Stubb” – Ricky Skaggs & Bruce Hornsby (2007), with Bruce Hornsby
“Sugar Daddy” – Boone Creek (1977), with Boone Creek
“Sugarfoot Rag” – That Down Home Feeling (1977), with Buck White and the Down Home Folks
“Summer Wages” – J.D. Crowe & the New South (1975), with J.D. Crowe and the New South
“Super Freak” – Ricky Skaggs & Bruce Hornsby (2007), with Bruce Hornsby
“Sweet Georgia Brown” – That’s It! (1975)
“Sweetheart You Done Me Wrong” – Honoring the Fathers of Bluegrass: Tribute to 1946 and 1947 (2008)
“Sweet Temptation” – Sweet Temptation (1979)
“Swing Down Sweet Chariot” – That Down Home Feeling (1977), with Buck White and the Down Home Folks
“Take Me Back” – Gospel Echoes and White Doves (1983)
“Talk About Sufferin'” – Skaggs & Rice (1980), with Tony Rice
“Ten Degrees” – J.D. Crowe & the New South (1975), with J.D. Crowe and the New South
“Tennessee Blues” – Skaggs & Rice (1980), with Tony Rice
“Tennessee Stud (For Doc Watson)” – Music to My Ears (2012)
“Thanks Again” – Comin’ Home to Stay (1988)
“Thanks Again (Sweethearts)” – Thanks Again (Sweethearts) single (2022), with Sharon White
“Thank You Lord” – That Down Home Feeling (1977), with Buck White and the Down Home Folks
“That’s It” – That’s It! (1975)
“The Angels Are Singing in Heaven Tonight” – Tribute to the Stanley Brothers (1971), with Keith Whitley
“The Banks of the Ohio” – The Three Pickers (2003)
“The Bubble Gum Song” – That’s It! (1975)
“The Christmas Guest” – A Skaggs Family Christmas: Volume One (2005), with the Whites and family
“The Darkest Hour Is Just Before Dawn” – Gospel Echoes and White Doves (1983)
“The Darkest Hour Is Just Before the Dawn” – Soldier of the Cross (1999)
“The Dreaded Spoon” – Ricky Skaggs & Bruce Hornsby (2007), with Bruce Hornsby
“The Fields of Home” – Kentucky Thunder (1989)
“The First Noel” – A Skaggs Family Christmas: Volume Two (2011), with the Whites and family
“The Joshua Generation” – Soldier of the Cross (1999)
“The Memory of Your Smile” – Boone Creek (1977), with Boone Creek
“The Old Crossroad Is Waiting” – Skaggs & Rice (1980), with Tony Rice
“The Old Crossroads” – Honoring the Fathers of Bluegrass: Tribute to 1946 and 1947 (2008)
“There’s More Pretty Girls Than One” – Skaggs & Rice (1980), with Tony Rice
“The River of Jordan” – Family & Friends (1982)
“The Selfishness in Man” – Life Is a Journey (1997)
“The Solid Rock” – Salt of the Earth (2007), with the Whites
“The Storms Are on the Ocean” – The Three Pickers (2003)
“The Way It Is” – Cluck Ol’ Hen (2013)
“The Will” – The Will single (2024), with Sharon White
“The Window Up Above” – Country Boy (1984)
“Things in Life” – Music to My Ears (2012)
“Think of What You’ve Done” – Family & Friends (1982)
“This Old House” – Salt of the Earth (2007), with the Whites
“This Weary Heart You Stole Away” – Second Generation Bluegrass (1972), with Keith Whitley
“This World Is Not My Home” – Solo: Songs My Dad Loved (2009)
“Those Two Blue Eyes” – Second Generation Bluegrass (1972), with Keith Whitley
“Time Is a Bandit” – Life Is a Journey (1997)
“Too Far Down to Fall” – History of the Future (2001)
“Too Late to Cry” – Tribute to the Stanley Brothers (1971), with Keith Whitley
“Toy Heart” – Family & Friends (1982)
“Try a Little Kindness” – That Down Home Feeling (1977), with Buck White and the Down Home Folks
“Two Highways” – Country Boy (1984)

U–Z

“Uncle Pen” – Don’t Cheat in Our Hometown (1983)
“Uncle Pen (Bluegrass version)” – Country Hits Bluegrass Style (2011)
“Used to Be” – Big Mon: The Songs of Bill Monroe (2000), with the Whites
“Voices Singin'” – Life Is a Journey (1997)
“Waitin’ for the Sun to Shine” – Waitin’ for the Sun to Shine (1981)
“Waiting at the Gate” – Soldier of the Cross (1999)
“Walkin’ in Jerusalem” – Boone Creek (1977), with Boone Creek
“Walk On Boy” – The Three Pickers (2003)
“Walk Softly on This Heart of Mine” – Big Mon: The Songs of Bill Monroe (2000), with the Dixie Chicks
“Walls of Time” – Ancient Tones (1999)
“Wayward to Hayward” – Instrumentals (2006)
“We Live in Two Different Worlds” – Family & Friends (1982)
“We’ll Be Sweethearts in Heaven” – Tribute to the Stanley Brothers (1971), with Keith Whitley
“Well Glory!” – Bluegrass Rules! (1997)
“Were You There When They Crucified My Lord” – Soldier of the Cross (1999)
“What Are You Waiting For” – Music to My Ears (2012)
“What Child Is This?” – A Skaggs Family Christmas: Volume One (2005), with the Whites and family
“What Is a Home Without Love?” – The Three Pickers (2003)
“What Is a Home Without Love” – Solo: Songs My Dad Loved (2009)
“What Songs Were Sung” – A Skaggs Family Christmas: Volume Two (2011), with the Whites and family
“What Would You Give in Exchange for Your Soul?” – The Three Pickers (2003)
“Wheel Hoss” – Country Boy (1984)
“When” – Solid Ground (1995)
“When I Love” – Kentucky Thunder (1989)
“When I’m Good and Gone” – Hearts Like Ours (2014), with Sharon White
“When Life Hits Hard” – Life Is a Journey (1997)
“When We Meet on That Evergreen Shore” – That’s It! (1975)
“When You’re Lonely” – Honoring the Fathers of Bluegrass: Tribute to 1946 and 1947 (2008)
“Where I Stand (Acoustic)” – Where I Stand (Acoustic) single (2014), with High Valley
“Where the Soul Never Dies” – Skaggs & Rice (1980), with Tony Rice
“White Christmas” – A Skaggs Family Christmas: Volume One (2005), with the Whites and family
“White Dove” – Tribute to the Stanley Brothers (1971), with Keith Whitley
“White House Blues” – Boone Creek (1977), with Boone Creek
“Whitesburg” – That’s It! (1975)
“White Wheeled Limousine” – Cluck Ol’ Hen (2013)
“Who Will Sing for Me?” – The Three Pickers (2003)
“Why Did I Wait So Long” – Brand New Strings (2004)
“Why Did You Wander” – Live at the Charleston Music Hall (2003)
“Why Don’t You Tell Me So” – New South Live (1975)
“Why I’m Walkin'” – Comin’ Home to Stay (1988)
“Wildwood Flower” – Second Generation Bluegrass (1972), with Keith Whitley
“Willie Is Coming Home” – Willie Is Coming Home single (2025)
“Will the Roses Bloom (Where She Lies Sleeping)” – Skaggs & Rice (1980), with Tony Rice
“Wings of a Dove” – Salt of the Earth (2007), with the Whites
“Wings of Angels” – Gospel Echoes and White Doves (1983)
“Winter Wonderland” – A Skaggs Family Christmas Live (bonus DVD) (2011)
“Woman You Won’t Break Mine” – Comin’ Home to Stay (1988)
“Won’t It Be Wonderful There” – Family & Friends (1982)
“Working on a Building” – Gospel Echoes and White Doves (1983)
“Wreck on the Highway” – Salt of the Earth (2007), with the Whites
“You Are Something Else” – Music to My Ears (2012)
“You Are What I Am” – New South Live (1975)
“You Can’t Hurt Ham” – Music to My Ears (2012)
“You Can’t Take It with You When You Go” – My Father’s Son (1991)
“You Don’t Count the Cost” – My Father’s Son (1991)
“You’ll Find God” – Mosaic (2010)
“You Make Me Feel Like a Man” – Live in London (1985)
“You May See Me Walkin'” – Waitin’ for the Sun to Shine (1981)
“You’re Going Away” – Gospel Echoes and White Doves (1983)
“Your Old Love Letters” – Waitin’ for the Sun to Shine (1981)
“Your Selfish Heart” – History of the Future (2001)
“You’ve Got a Lover” – Highways & Heartaches (1982)
“You’ve Got a Lover (Bluegrass version)” – Country Hits Bluegrass Style (2011)