In order to make some sense out of this list we had to make a rule that no duet partner can appear more than once on this list. The main reasons for that rule was fueled by the names Carly Simon and Carole King. James Taylor has sung so many songs with Carole King and Carly Simon we could fill a top 100 James Taylor Duets list just between the three of them. Some of our choices are studio recordings while some of the picks come from live concerts and television specials. There is something very special about each performance we have chosen. We hope you enjoy this list. You will be amazed at all of these performances.
# 10 –I Think It’s Gonna Work Out Fine (with Linda Ronstadt)
Well there is no better way to start out this list than with one of the greatest female voices in popular music history. Linda Ronstadt ruled the airwaves in the 1970’s with hit after hit. Her golden voice blends so perfectly with James Taylors. The song “I Think It’s Gonna Work Out Fine,” was released on Linda Ronstadt’s 1982 Get Closer album. The song was written by Rose Marie McCoy and Sylvia McKinney. It was originally a hit for Ike & Tina Turner in 1961.
# 9 – Baby It’s Cold Outside (with Natalie Cole)
“Baby It’s Cold Outside,” is one of the most popular recorded duets of all time. It has been recorded by some of the greatest singers in history. James Taylor‘s and Natalie Cole’s version stands at the top of that list of artists who have recorded this magical Christmas Song. This one has always been a song about chemistry, and Taylor and Cole play the part perfectly. The song was first released on the James Taylor record, James Taylor A Christmas Album. The album was released in 2004
# 8 – Oh Susanna (with Johnny Cash)
When you listen to James Taylor sing the opening line of “Oh Susanna,” you quickly realize that Taylor could basically take any melody and turn it into an enchanted listening experience. Taylor sings the majority of the song until Johnny Cash appears at the end. The camera angle of Cash simply defines how cool that man was. The performance in this video is from the Johnny Cash Television Show. The performance aired on Feb. 17, 1971
# 7 – For Free (with Joni Mitchell)
Although James Taylor only sings harmony at the end of this song, his guitar playing so beautifully blended with Joni’s voice and piano. It’s a clear representation that a brilliant duet does not have to only center around vocals. Listen to Taylor’s guitar lines dance in between Joni Mitchell’s rolling piano chords. It just gives you chills to hear something so organic and heartfelt. It defines the heart and soul of two artists of such depth. The performance was from their London Paris Show in 1970. It was aired on the BBC on the John Peel’s Sunday Show
# 6 – Crying in the Rain (with Art Garfunkel)
On the song “Crying in the Rain,” James Taylor teamed up with one of the greatest duet singers in music history. It can be easily argued that Art Garfunkel defines one of the most beautiful angelic male voices in the music industry. Garfunkel’s work with Paul Simon represented some of the most loved songs of the 1960’s to 70’s. It was destiny that the golden voice of James Taylor would eventually team up with angelic voice of Art Garfunkel. The duet appeared on Art Garfunkel’s 1993 album Up Till Now.
# 5 –Carolina in my Mind (with The Dixie Chicks)
“Carolina in my Mind,” has always been one of James Taylor’s most loved songs. His duet with the Dixie Chicks on the classic track was simply mesmerizing. The two artists traded back and forth songs on VH1’s Crossroads show. There were so many highlights from the broadcast that it was almost impossible to pick only one song to be represented here on the James Taylor Duets list. However, the beauty of the performance of “Carolina on my Mind,” was to mesmerizing to ignore. The original broadcast of the VH1 Crossroads show aired on Friday October 18th 2002.
# 4 – Mockingbird (with Carly Simon)
Do you remember when this songs was first released back in 1974? It was such a huge hit and one could not turn the radio dial without running into this one on multiple stations at any given minute of the day. James Taylor recorded so many classic songs with Carly Simon that it almost seems criminal to only include one song on the list. Nonetheless, in order to represent all those other wonderful artists we had to pick only one with Carly Simon. We simply thought “Mockingbird,” was the most fun.
# 3 – Her Town Two (with J.D. Souther)
The harmonizing on this one between James Taylor is J.D. Souther is as heavenly as it gets. It is also the only song that we included on both of the Top 10 James Taylor Songs and Top 10 James Taylor Duets lists. The video below is from a live performance in the 1980’s. The original version was released on James Taylor’s 1981 album Dad Loves His Work. The song was written by James Taylor, J.D. Souther and Waddy Wachtel.
# 2 – How’s The World Treating You (with Alison Krauss)
Well this one is quite striking. It may be hard to maintain one’s emotions when listening to this beautiful duet between Alison Krauss and James Taylor. At first, many fans may be surprised to see this one so high on the list. But one listen is all you need to be convinced the song’s importance. The song was written by Chet Atkins and Boudleaux Bryant and had been originally recorded by Elvis Presley. This version appears on the Alison Krauss album, A Hundred Miles or More: A Collection.
# 1 – You Got a Friend (with Carole King)
Well how could this one not be No.1? The beauty of this duet is so striking it’s almost unbearable. Two of America’s most loved singer songwriters together singing one of the greatest loves songs ever written. Listening to them sing together awakens a roller-coaster of memories for so many people who grew up in the 1970’s. The song was written by Carole King in 1971. It was recorded in two versions that appeared simultaneously on both Carole King’s and James Taylor’s solo albums in 1971.
Updated Nov 10, 2020