Top 10 Kris Kristofferson Songs

Photo: Bryan Ledgard, CC BY 2.0 <https://creativecommons.org/licenses/by/2.0>, via Wikimedia Commons

Our Top 10 Kris Kristofferson Songs list looks at one of the most famous names in show business. Sadly, Kris Kristofferson passed away on September 29, 2024. Known originally as a songwriter, Kris Kristofferson also celebrated a successful recording career. Early on, Kris Kristofferson enjoyed success as a songwriter, composing multiple number-one hits for various artists in the late 1960s. In 1970, Kris Kristofferson released his first studio album, featuring versions of his hit songs and more. Throughout his career, Kris Kristofferson would collaborate with multiple musical artists, including a run of albums with his wife, Rita Coolidge. In 1985, he formed The Highwayman group with Johnny Cash, Waylon Jennings, and Willie Nelson.

Kris Kristofferson also appeared in several motion pictures. His most famous role was co-starring with Barbra Streisand in the 1975 motion picture A Star Is Born. It was a brilliant performance that some thought was inspired by his relationship with Janis Joplin, although the film was indeed a remake.

Our Top 10 Kris Kristofferson Songs list presents a variety of his songs, focusing on his songwriting, with a few exceptions. The list includes songs recorded by Kris Kristofferson and some of the artists who made his songs famous.

# 10 – Border Lord

We open our Top 10 Kris Kristofferson Songs list with one of the songwriter’s most underrated songs. The brilliant song “Border Lord” was released on Kris Kristofferson’s third solo album, Border Lord. The album was released in 1972. This one is dark, moody, and so captivating. The song was written by Kris Kristofferson, Stephen Bruton, Donnie Fritts, and Terry Paul,

# 9 – Highwayman

We had to include this one. This great Grammy Award-winning song entitled “Highwayman” was recorded in 1985 with the group The Highwaymen; it was a legendary collaboration between Kris Kristofferson, Johnny Cash, Waylon Jennings, and Willie Nelson, four legendary artists coming together in a group that was sort of an outlaw version of the Traveling Wilburys. Four of country music’s biggest stars of all time formed a supergroup for the ages. The four legends released three albums as the Highwaymen. The great song “Highwayman” was written by another songwriting legend named Mr. Jimmy Webb. This one went straight to number one on the Country music charts.

# 8 – The Taker

At number eight on this top 10 Kris Kristofferson songs list is the excellent song “The Taker.” The song was released on Kris Kristofferson’s debut album, Kristofferson. Presented here is the excellent Waylon Jennings version.

# 7 – Sunday Mornin’ Comin’ Down

“Sunday Mornin’ Comin’ Down” is one of the greatest Kris Kristofferson songs ever written. Kris Kristofferson composed the song in 1969. It was initially a hit for singer Ray Stevens. However, the memorable Johnny Cash version blew everyone away with its greatness. The Johnny Cash version hit number one on the Billboard Country music charts in 1970. “Sunday Mornin’ Comin’ Down” was also named Song Of The Year by the Country Music Association in 1970.

# 6 – Lover Please (with Rita Coolidge)

This great duet with Rita Coolidge appeared on the album Full Moon. It is one of the rare songs on this list recorded by Kris Kristofferson that he did not write. However, this recording, which he released with his wife, Rita Coolidge, was so stirring that we had to include it on this list. The music industry also agreed that Kris Kristofferson and Rita Coolidge’s version was brilliant. They were awarded a Grammy Award in 1975. The song was released on the album Breakaway.

# 5 – Lovin’ Her Was Easier (Than Anything I’ll Ever Do Again)

At the halfway point on our top 10 Kris Kristofferson songs list, we turn to Kris Kristofferson’s first single to chart, which he released on his own. This is a beautiful song. It was a top 30 hit on the U.S. Billboard Hot 100. It did even better on the Billboard Adult Contemporary charts, peaking at number four in 1971. The song was released on the album The Silver Tongued Devil and I.

# 4 – Why Me

While Kris Kristofferson had many number-one songs, other artists always performed them. Kris Kristofferson’s biggest hit single, released himself, was “Why Me.” The song was released on his 1973 album entitled Jesus Was a Capricorn. The song was released as the third single from the album. It hit number one on the Billboard Country music charts and broke the top 20 on the Billboard Hot 100.

# 3 – For The Good Times

The following three songs on this Kris Kristofferson Songs list were all released on Kris Kristofferson’s 1970 debut album entitled Kristofferson. However, some of them had already been recorded by other musical artists with huge hit singles. Kris Kristofferson’s legendary song “For The Good Times” was first recorded by Ray Price in 1968. Raye Price benefited greatly from recording Kris Kristofferson’s “For The Good Times,” as Price wound up with a number-one country record with “For The Good Times” on the Billboard Country music charts in 1968. Al Green would also have a big hit with the song in 1970. So many others would record the song, including Frank Sinatra, Elvis Presley, Jerry Lee Lewis, and Johnny Cash.

# 2 – Help Me Make It Through The Night

As we wind down our top 10 Kris Kristofferson Songs list, we turn to the classic Kris Kristofferson song “Help Me Make It Through The Night.” The song was released on Kris Kristofferson’s 1970 album, Kristofferson. However, country singer Sammi Smith would have a massive hit single with the song. Sammi Smith released the song “Help Me Make It Through The Night” as a single in 1970. Her version went straight to number one on the Billboard Country music charts. It also became a top 10 single on the Billboard Hot 100. It would become the singer’s signature song. Hundreds of artists have recorded the song, from Elvis Presley to Glen Campbell to Gladys Knight & the Pips to many more. The song “Help Me Make It Through The Night” won a Grammy Award for Song Of The Year in 1971.

# 1 – Me And Bobby McGee

We close out our Top 10 Kris Kristofferson Songs with one of the most famous songs Kris Kristofferson ever composed. The song “Me and Bobby McGee” was written by Kris Kristofferson and Fred Foster. The song has been covered by many artists over the years. However, it was widely covered early on when it was first released. The first cover version of the song was recorded by a country artist named Roger Miller. The country artist had a top 20 hit with the song on the Billboard Country Charts in 1969. However, the world would discover the song due to the great Janis Joplin version recorded in 1971.

Janis Joplin recorded the song “Me and Bobby McGee” to be included on her album Pearl. Sadly, Janis Joplin died just a few days after she recorded the song. Janis Joplin never got to see how big the song would become. Janis Joplin’s version hit number one on the Billboard Hot 100. It would become the singer’s only number-one hit.

“Me and Bobby McGee” was also recorded by Gordon Lightfoot, who had a top 20 hit with the song in Canada in 1970. Kenny Rogers and his band, The First Edition, released a version of “Me and Bobby McGee” in 1969. Jerry Lee Lewis had a top 40 hit with it on the Billboard Hot 100 in 1971. While the list of artists who have recorded the song exceeds the limits of space in this article, the ones we would also like to mention include great versions by The Grateful Dead, Joan Baez, Melissa Etheridge, Loretta Lynn, Johnny Cash, The Highwayman, and, of course the wonderful version released by the song’s composer, Kris Kristofferson.