Top Duet Songs of All Time – Kickin’ it Old School

Happy Valentine’s Day to you all. This is supposed to be one of the most romantic days of the year and when I think of romance, I think of music. When I was checking out the Retro Crush website like I regularly do I noticed that they had a feature on the 25 greatest duets of all time. Since many duets are love songs and today is Valentine’s Day, I thought I would put together my own list.

First, there is some confusion between what constitutes a duet or a collaboration, so I am just going to go with collaboration to simplify things. Second, I will not consider Christmas songs in this particular list because there are so many holiday duets and it is difficult to compare them to non-holiday songs. Third, I will only consider songs where the singers are not already a member of the same group, so songs by Simon & Garfunkel or Hall & Oates will not count towards my list. Last, I will only consider songs where the collaboration is between two vocalists and not only a musician, so songs featuring Santana or Jim Brickman will not count towards my list. Those are the rules that I used to compile my list and also remember these are what I consider to be my favorites and not necessarily the “best” of the category.

I usually give you just the top 10, but because there are so many great songs in this category I will give you a bonus 15 for a total of 25 songs. Actually, there will be even more than 25 songs because I will combine multiple songs featuring the same artist for the sake of this list. Also enjoy the links to the videos for most songs.  Let’s get right to it. Here are OLD SCHOOL’S TOP 10 FAVORITE SONG COLLABORATIONS/DUETS (+ Bonus 15):
Honorable Mention. “Walk This Way” by Run DMC with Aerosmith. Run DMC AerosmithThis was a groundbreaking crossover song for rap music at the time. It broke down so many barriers for rap and hip hop music at the time and that is why I have to at least give it honorable mention.

25. “You’ve Got a Friend in Me” by Randy Newman with Lyle Lovett – From the movie Toy Story [link to video of live performance]

24. “Crazy In Love” Beyonce JayZby Beyoncé with Jay-Z [link to video]


23. “My Boo” by Usher with Alicia Keys [link to video]  

22. “Heard ‘em Say” by Kanye West with Adam Levine (from Maroon 5) [link to video]

21. “Over and Over” by Nelly with Tim McGraw [link to video]

20. “Somewhere Out There” by James Ingram with Linda Rondstadt AND “Baby Come To Me” by James Ingram with Patti Austin – Both songs feature the great James Ingram who is a fantastic duet partnerEasy Lover [link to video for “Somewhere Out There”]

19. “Easy Lover” by Phil Collins with Philip Bailey (from Earth, Wind & Fire) [link to video]

18. “Silent Prayer” by Shanice with Johnny Gill [link to song playing]

17. “Almost Paradise” by Ann Wilson and Mike Reno – From the movie Footloose [link to video] – also ranks on my Top Songs from 80s Movies list

16. “Endless Love” by Lionel Richie and Diana Ross – Also an outstanding remake by Luther Vandross with Mariah CareySay Say Say [link to live performance]

15. “Say Say Say” by Paul McCartney with Michael Jackson – The two also combined for the song “The Girl is Mine” [link to video]

14. “Crazy Love” by Aaron Neville with Robbie Robertson – Outstanding version of this song featured in the film Phenomenon [link to video of scene from movie featuring song]

13. “Love Is” by Brian McKnight with Vanessa Williams AND “My Kind of Girl” by Brian McKnight with Justin TimberlakeMcKnight – Both songs feature Brian McKnight who is one of my favorite voices in all of music [link to video for “Love Is”]

12. “U Got the Look” by Sheena Easton with Prince AND “We’ve Got Tonight” by Sheena Easton with Kenny Rogers – Both songs feature Sheena Easton [link to video for “We’ve Got Tonight”]

11. “You and I” by Eddie Rabbit and Crystal Gayle – This was one of our wedding songs, so it will always hold a dear place for me [link to song playing]

10. “Don’t Give Up” by Peter Gabriel with Kate Bush – I recently came across an amazing remake of this haunting song by Bono and Alicia Keys [link to video]

9. “Leather and Lace” by Stevie Nicks with Don Henley AND “Whenever I Call You Friend” by Kenny Loggins with Stevie Nicks AND “Stop Dragging My Heart Around” by Stevie Nicks with Tom Petty – All three songs feature Stevie Nicks who is a natural at duets after her time as part of Fleetwood Mac [link to song playing for “Leather and Lace”]

8. “What Have I Done To Deserve This” by The Pet Shop Boys with Dusty Springfield – One of the most under-rated songs from the 80’sCetera [link to video]

7. “Feels Like Heaven” by Peter Cetera with Chaka Khan AND “After All” by Peter Cetera with Cher AND “The Next Time I Fall in Love” by Peter Cetera with Amy Grant – What can I say? I love Peter Cetera duets. [link to video of live performance of “Feels Like Heaven”]

6. “I Knew You Were Waiting (For Me)” by George Michael with Aretha Franklin – One of my favorite 80’s tunes [link to video]

5. “Don’t Go Breaking My Heart” by Elton John with Kiki Dee – Fun from start to finishDr. Dre [link to video]

4. “Nuthin’ But a G Thang” by Dr. Dre with Snoop Dogg AND “California Love” by Dr. Dre with 2pac AND “Forgot About Dre” by Dr. Dre with Eminem – All three songs feature the incredible Dr. Dre [link to video for “Nuthin’ But a G Thang”]

3. “Under Pressure” by Queen with David Bowie [link to video]

2. “One Sweet Day” by Mariah Carey with Boyz II MenGaye & Terrell [link to video]

1. “You’re All I Need to Get By” by Marvin Gaye with Tammi Terrell AND “Ain’t Nothing Like the Real Thing” by Marvin Gaye with Tammi Terrell AND “Ain’t No Mountain High Enough” by Marvin Gaye with Tammi Terrell – These two made a perfect combination and went on to make some of the best duets of all time [link to song playing for “You’re All I Need to Get By”]

There’s my list. This was difficult because I found that there are a lot of quality duets and collaborations out there. The order can be debated and I kind of cheated by combining some songs within the same rank if I felt it made sense. What songs do you feel are missing??? If you have never heard any of the songs on this list, I suggest you go give them a listen since I provided links for most of the songs. I would say that at least 17 of the 25 would be considered love songs, so it makes this list very appropriate on this romantic holiday.  IF YOU LIKE THIS LIST, you should definitely check out my list of Best Duets from the 80s which includes video links to many of the songs.

That will do it for this issue of Kickin’ it Old School. Hope you enjoyed it and thanks so much for reading. Please click on the archive buttons on the left to make sure you have not missed any previous issues. If you like what you read, please tell a friend or two. Peace and much love.

Check this out: Here is a link to some interesting information regarding the history of Valentine’s Day… www.history.com/minisites/valentine/

Quote of the day: “Knowledge is gained by learning; trust by doubt; skill by practice; and Love by Love.” -Thomas Szasz
+ Bonus Quote for Valentine’s Day: “Love one another and you will be happy. It’s as simple and difficult as that.” -Michael Leunig

Download this: I would recommend any of the songs from the above list, but I am just going to pick just two for this feature… “Crazy Love” by Aaron Neville with Robbie Robertson and “Don’t Give Up” by Peter Gabriel with Kate Bush


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  1. I think Paul should have been higher on the list, but well, it WAS with MJ, so that explains it all LOL.

  2. Personally, I have a soft spot for Natalie Cole and Nat King Cole singing “Unforgettable”

  3. Reply to: emerging
    That’s a good one, E. I guess I did not think of that one since she did not make the song until after her father had passed already. They made that song similar to the way Alicia Keys and Frank Sinatra performed together at last Sunday’s Grammy’s. Either way it is still a good song.
    Thanks for reading and commenting.

  4. sometimes love just aint enough by Patti Smyth & Don Henley, It’s your love by Tim-McGraw and Faith Hill, I wanna take forever toninght by Peter Cetera & Crystal Bernard

  5. Awesome songs; I can name duet after duet because there are so many good ones. You’ve listed some of the best! I’d add: All of Me by Diana Ross and Julio Iglesias…..there are SO many!

  6. Old school, you left out Donny Hathaway and Roberta Flack, “The Closer I Get To You” and “Where Is The Love” Hathaway, and Flack can duet with the best of them.

  7. you forgot if this world were mine by luther vandross and cheryl lynn…should be your no. 1…you have to listen to it…

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