Perhaps the most celebrated – and poignant – collaboration ever between a legacy performer and a newer musical star came to an end on Sept. 30, 2021, with the release of “Love for Sale,” the final album by legendary vocalist Tony Bennett, and his second with chart-topping singer-songwriter Lady Gaga. At the time, she was 35; he had turned 95 two months before.
The unlikely duo made their recording debut with “Cheek to Cheek” in 2014, then toured off and on together for the next seven years, their final live appearance coming just a month before “Love for Sale.” What made the collaboration poignant is that Bennett had been diagnosed with Alzheimer’s disease in 2016, but continued to record and perform as his memory deteriorated, and it was said that whatever his mental state at the time, when he was in front of a microphone, he came alive, remembering every word, every note.
Though both of the unlikely musical couple’s albums reached the top 10 on the Billboard 200, they never charted a single on the publication’s Hot 100. However, though the age differences are nowhere near as dramatic, there are numerous examples of newer, younger artists recording with performers who had their first Billboard chart hits decades ago – sometimes as far back as the 1960s. (These are the biggest comebacks in music history.)
To determine the most successful musical collaborations between newer artists and legacy acts, 24/7 Tempo reviewed chart performance from the Billboard Hot 100. Collaborations were ranked based on an inverse score wherein a week at No. 1 on the Hot 100 is worth 100 points, a week at No. 2 is worth 99 points, and so on, up to a week at No. 100 worth one point. Chart data is current through Sept. 9, 2023. (Billboard sources its data from Luminate, a company collecting data on music and other entertainment forms.)
Only songs whose artists first entered the Hot 100 at least 20 years apart were considered – and in some cases, the gap was much greater than that. Take, for example, the 2021 Elton John-Dua Lipa offering “Cold Heart (PNAU Remix).” Lipa’s initial entry into the Hot 100 came with “New Rules” on Aug. 19, 2018. Elton John – who appears more than any other performer on this list – made the first of his 68 (to date) appearances on the chart with “Border Song” on Aug. 15, 1970. (Here’s a catalog of Elton John’s biggest hits, according to Billboard.)
40. will.i.am ft. Mick Jagger & Jennifer Lopez, “T.H.E (The Hardest Ever)”
> Peak position on the Hot 100: No. 36 (for 1 week)
> Total time on the Hot 100: 8 weeks
> Entered the Hot 100: Dec. 10, 2011
39. Ed Sheeran & Elton John, “Merry Christmas”
> Peak position on the Hot 100: No. 42 (for 1 week)
> Total time on the Hot 100: 6 weeks
> Entered the Hot 100: Dec. 18, 2021
38. Kanye West ft. Paul McCartney, “Only One”
> Peak position on the Hot 100: No. 35 (for 1 week)
> Total time on the Hot 100: 8 weeks
> Entered the Hot 100: Jan. 17, 2015
37. Jimmy Buffett with Clint Black, Kenny Chesney, Alan Jackson, Toby Keith & George Strait, “Hey Good Lookin'”
> Peak position on the Hot 100: No. 63 (for 1 week)
> Total time on the Hot 100: 11 weeks
> Entered the Hot 100: June 19, 2004
36. Madonna ft. Nicki Minaj & M.I.A., “Give Me All Your Luvin'”
> Peak position on the Hot 100: No. 10 (for 1 week)
> Total time on the Hot 100: 6 weeks
> Entered the Hot 100: Feb. 18, 2012
35. Summer Walker & Usher, “Come Thru”
> Peak position on the Hot 100: No. 42 (for 1 week)
> Total time on the Hot 100: 19 weeks
> Entered the Hot 100: Oct. 19, 2019
34. Aretha Franklin/Whitney Houston, “It Isn’t, It Wasn’t, It Ain’t Never Gonna Be”
> Peak position on the Hot 100: No. 41 (for 1 week)
> Total time on the Hot 100: 8 weeks
> Entered the Hot 100: July 1, 1989
33. The Art Of Noise ft. Duane Eddy, “Peter Gunn”
> Peak position on the Hot 100: No. 50 (for 1 week)
> Total time on the Hot 100: 11 weeks
> Entered the Hot 100: May 17, 1986
32. LL Cool J ft. The-Dream, “Baby”
> Peak position on the Hot 100: No. 52 (for 1 week)
> Total time on the Hot 100: 11 weeks
> Entered the Hot 100: Aug. 9, 2008
31. Elton John & LeAnn Rimes, “Written In The Stars”
> Peak position on the Hot 100: No. 29 (for 1 week)
> Total time on the Hot 100: 10 weeks
> Entered the Hot 100: March 13, 1999
30. The Weeknd, Playboi Carti & Madonna, “Popular”
> Peak position on the Hot 100: No. 43 (for 1 week)
> Total time on the Hot 100: 13 weeks
> Entered the Hot 100: June 17, 2023
29. The Art Of Noise ft. Tom Jones, “Kiss”
> Peak position on the Hot 100: No. 31 (for 2 weeks)
> Total time on the Hot 100: 11 weeks
> Entered the Hot 100: Dec. 3, 1988
28. Kenny Chesney With Mac McAnally, “Down the Road”
> Peak position on the Hot 100: No. 47 (for 1 week)
> Total time on the Hot 100: 18 weeks
> Entered the Hot 100: Dec. 20, 2008
27. Kanye West ft. Theophilus London, Allan Kingdom & Paul McCartney, “All Day”
> Peak position on the Hot 100: No. 15 (for 1 week)
> Total time on the Hot 100: 15 weeks
> Entered the Hot 100: March 21, 2015
26. Lil’ Duval ft. Snoop Dogg & Ball Greezy, “Smile (Living My Best Life)”
> Peak position on the Hot 100: No. 56 (for 1 week)
> Total time on the Hot 100: 19 weeks
> Entered the Hot 100: Sept. 8, 2018
25. Janet ft. Missy Elliott, P. Diddy & Carly Simon, “Son of a Gun”
> Peak position on the Hot 100: No. 28 (for 1 week)
> Total time on the Hot 100: 12 weeks
> Entered the Hot 100: Nov. 24, 2001
24. Bizarrap & Shakira, “Bzrp Music Sessions, Vol. 53”
> Peak position on the Hot 100: No. 9 (for 1 week)
> Total time on the Hot 100: 15 weeks
> Entered the Hot 100: Jan. 28, 2023
23. Keith Urban Duet With Pink, “One Too Many”
> Peak position on the Hot 100: No. 52 (for 1 week)
> Total time on the Hot 100: 34 weeks
> Entered the Hot 100: Oct. 3, 2020
22. Kenny Chesney With The Wailers, “Everybody Wants To Go to Heaven”
> Peak position on the Hot 100: No. 41 (for 1 week)
> Total time on the Hot 100: 20 weeks
> Entered the Hot 100: Aug. 30, 2008
21. Brad Paisley ft. Dolly Parton, “When I Get Where I’m Going”
> Peak position on the Hot 100: No. 39 (for 1 week)
> Total time on the Hot 100: 20 weeks
> Entered the Hot 100: Dec. 3, 2005
20. Eurythmics & Aretha Franklin, “Sisters Are Doin’ It for Themselves”
> Peak position on the Hot 100: No. 18 (for 1 week)
> Total time on the Hot 100: 15 weeks
> Entered the Hot 100: Oct. 19, 1985
19. Post Malone ft. Ozzy Osbourne & Travis Scott, “Take What You Want”
> Peak position on the Hot 100: No. 8 (for 1 week)
> Total time on the Hot 100: 20 weeks
> Entered the Hot 100: Sept. 21, 2019
18. Mariah Carey ft. Miguel, “#Beautiful”
> Peak position on the Hot 100: No. 15 (for 2 weeks)
> Total time on the Hot 100: 16 weeks
> Entered the Hot 100: May 25, 2013
17. Elton John & Britney Spears, “Hold Me Closer”
> Peak position on the Hot 100: No. 6 (for 1 week)
> Total time on the Hot 100: 20 weeks
> Entered the Hot 100: Sept. 10, 2022
16. The KLF ft. Tammy Wynette, “Justified and Ancient”
> Peak position on the Hot 100: No. 11 (for 2 weeks)
> Total time on the Hot 100: 18 weeks
> Entered the Hot 100: Feb. 1, 1992
15. Macklemore & Ryan Lewis ft. Eric Nally, Melle Mel, Kool Moe Dee & Grandmaster Caz, “Downtown”
> Peak position on the Hot 100: No. 12 (for 1 week)
> Total time on the Hot 100: 20 weeks
> Entered the Hot 100: Sept. 12, 2015
14. Fat Boys & The Beach Boys, “Wipeout”
> Peak position on the Hot 100: No. 12 (for 2 weeks)
> Total time on the Hot 100: 19 weeks
> Entered the Hot 100: July 11, 1987
13. Brandy, Tamia, Gladys Knight & Chaka Khan, “Missing You (From “Set It Off”)”
> Peak position on the Hot 100: No. 25 (for 3 weeks)
> Total time on the Hot 100: 20 weeks
> Entered the Hot 100: Aug. 24, 1996
12. Aretha Franklin & George Michael, “I Knew You Were Waiting (For Me)”
> Peak position on the Hot 100: No. 1 (for 2 weeks)
> Total time on the Hot 100: 17 weeks
> Entered the Hot 100: Feb. 21, 1987
11. Toby Keith Duet With Willie Nelson, “Beer for My Horses”
> Peak position on the Hot 100: No. 22 (for 1 week)
> Total time on the Hot 100: 20 weeks
> Entered the Hot 100: May 3, 2003
10. Santana ft. Chad Kroeger, “Into the Night”
> Peak position on the Hot 100: No. 26 (for 2 weeks)
> Total time on the Hot 100: 21 weeks
> Entered the Hot 100: Oct. 20, 2007
9. Pet Shop Boys & Dusty Springfield, “What Have I Done To Deserve This?”
> Peak position on the Hot 100: No. 2 (for 2 weeks)
> Total time on the Hot 100: 18 weeks
> Entered the Hot 100: Dec. 12, 1987
8. Zac Brown Band ft. Jimmy Buffett, “Knee Deep”
> Peak position on the Hot 100: No. 18 (for 1 week)
> Total time on the Hot 100: 20 weeks
> Entered the Hot 100: May 28, 2011
7. Dr. Dre ft. Eminem & Skylar Grey, “I Need a Doctor”
> Peak position on the Hot 100: No. 4 (for 1 week)
> Total time on the Hot 100: 20 weeks
> Entered the Hot 100: Feb. 19, 2011
6. Rihanna & Kanye West & Paul McCartney, “FourFiveSeconds”
> Peak position on the Hot 100: No. 4 (for 1 week)
> Total time on the Hot 100: 20 weeks
> Entered the Hot 100: Feb. 7, 2015
5. Uncle Kracker ft. Dobie Gray, “Drift Away”
> Peak position on the Hot 100: No. 9 (for 1 week)
> Total time on the Hot 100: 35 weeks
> Entered the Hot 100: March 29, 2003
4. Santana ft. Michelle Branch, “The Game of Love”
> Peak position on the Hot 100: No. 5 (for 3 weeks)
> Total time on the Hot 100: 37 weeks
> Entered the Hot 100: Oct. 5, 2002
3. Lil Nas X ft. Billy Ray Cyrus, “Old Town Road”
> Peak position on the Hot 100: No. 1 (for 19 weeks)
> Total time on the Hot 100: 45 weeks
> Entered the Hot 100: March 16, 2019
2. Elton John & Dua Lipa, “Cold Heart (PNAU Remix)”
> Peak position on the Hot 100: No. 7 (for 1 week)
> Total time on the Hot 100: 52 weeks
> Entered the Hot 100: Aug. 28, 2021
1. Santana ft. Rob Thomas, “Smooth”
> Peak position on the Hot 100: No. 1 (for 12 weeks)
> Total time on the Hot 100: 58 weeks
> Entered the Hot 100: July 31, 1999